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Characters / Sly Cooper: Villains

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The various Rogues Galleries and independent villains for all the games are listed here. Sneak through here to return to the main page. Warning: unmarked spoilers ahead.

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Sly Cooper and the Thievius Raccoonus


The Fiendish Five

A gang of five criminals who broke into Sly's home and killed his parents, dividing the parts of the Thievius Raccoonus among themselves and taking off to the furthest corners of the world. Tropes involving them:

    Sir Raleigh
"How delightful! We have a guest. The only thing is... I HATE unexpected guests!"
Voiced by: Kevin Blackton

The Fiendish Five's chief machinist, Sir Raleigh is an aristocratic frog from Wales who, having grown bored with the high life, took up piracy on a whim and found it to his liking. Raleigh set up a shipwrecking operation on an island off the coast of Wales using a weather machine he made.

  • Aristocrats Are Evil: In his backstory, he was born into wealth and privilege before turning to a life of crime out of sheer boredom.
  • Balloon Belly: His main form of attack.
    "Soooo, without further ado, let me make amends by... what? BLOATING TO GARGANTUAN SIZE AND SQUASHING YOU LIKE THE INSIGNIFICANT BUG THAT YOU ARE!!"
  • British Teeth: As seen in the picture above.
  • The Cameo: He's seemed to be pretty well-liked amongst the games' developers, as he's referenced in almost every game except the third.
    • In the tie-in comics, he's shown to be an inmate at the same prison McSweeny is being held in.
    • In Sly 2, two pieces of art depicting him are used as portraits on the walls of the Museum in Egypt, as are the suits of armor and statue props from his level.
    • In the Goodbye, My Sweet short, his hat is in the first shot, resting in a bookshelf.
    • In Thieves in Time, his hat is a findable item in Medieval England that helpfully eliminates all water damage.
  • Chewing the Scenery
    "If you lazylow-brow…technically incompetent pack of guttersnipes DID YOUR JOBS RIGHT, we'd have sunk a hundred ships by now!"
    "And if any of you let him get his hands on that key, I'll personally flog the lot of you! FOR AN ENTIRE FORTNIGHT!"
  • Evil Brit: Speaks with a British accent, even though he comes from Wales. It helps that his voice actor is also from England.
  • Faux Affably Evil: He comes off as a Benevolent Boss at first on his P.A. announcements to his flunkies... before lapsing into berating them for various screw-ups and threatening to "flog them for an entire fortnight" if they can't catch the thief prowling around his lair... only to calm right back down, praising their current work and telling them to carry on with their business.
  • For the Evulz: He became a criminal out of boredom and quickly took to it.
  • Gadgeteer Genius: Not that he actually uses his machines in his boss-fight, which is actually rather gutsy, all things considered.
  • Half-Dressed Cartoon Animal: Wears a top hat, gloves, and spats, but no other clothing.
  • I Shall Taunt You: Should he manage to hit you, he pulls out his tongue and plucks it like a guitar string before deflating to his normal size.
  • Jerkass: At least the other members of the Fiendish Five had some sort of Freudian Excuse for turning to a life of crime. Him? He simply became a criminal because he was bored. For him, crime started out as a hobby and turned into an addiction.
  • Nice Hat: It seems to be a steampunk top-hat. In Thieves in Time, it can be found as an item that lets you avoid drowning.
  • Large Ham: Especially when he starts ranting.
  • Mood-Swinger: Drastically switches between sarcastic politeness and loud, scathing disdain at the slightest provocation.
  • Pirate: Turned to this out of boredom, and found it to his liking.
  • Pitiful Worms: He outright calls Sly an "insignificant bug" before their fight.
  • Put on a Bus: After being thrown in jail, Raleigh appeared in a few cameos within later games and had his hat show up as a treasure in Thieves in Time. Sir Raleigh has not been talked about or been relevant to the plot since the first game.
  • Salvage Pirates: His current operation hinges on causing shipwrecks, and scavenging the goods afterward.
  • Smug Snake: His bite isn't anywhere near the level of his bark.
  • Starter Villain: The first boss of the first game, and thus the series.
  • Suddenly SHOUTING!: Likes to flip from barely above a mumble to bellowing at the top of his lungs in the space of a single syllable.
  • Warmup Boss: As the first member of the Fiendish Five that Sly fights, Raleigh is an incredibly easy boss fight. As intimidating as he tries to make it sound, his bloating only grants him a slow, predictable pattern that is simple to come to grips with. He also lacks the stamina to do anything truly devastating with his strategy.
  • Would Hurt a Child: He states that he and the rest of the Fiendish Five should have killed Sly when he was a child.

"You break into my place, steal my stuff, trash the joint... I feel transgressed and violated! Let's rock!"
Voiced by: Kevin Blackton

An American bulldog with a serious inferiority complex who once had total control of Mesa City, Utah, until the Cooper Gang took him down. He returns to threaten the gang again in Holland but is taken out by a combination of Penelope's RC skills, Bentley's defense systems, Murray's strength, Sly's guile, and Carmelita's shock pistol. Before becoming a criminal, Muggshot was picked on as a puppy. Inspired by gangster movies, he dedicated his life to becoming big, strong and intimidating so he would never be picked on again.

  • Astonishingly Appropriate Appearance: Due to his exercise regime as a teen, an adult Muggshot developed into an immensely Top-Heavy Guy. It references the similarly front-loaded builds of non-anthropomorphic bulldogs.
  • Badass Mustache: That almost resembles a letter "M."
  • Berserk Button: "No one talks that way about my mother! NOBODY!"
  • The Brute: Fits the trope like a glove, seeing as he acted as the Fiendish Five's muscle. He acts in the same way when he goes independent, such as during the Flight of Fancy episode in Honor Among Thieves.
  • Bully Bulldog: When he was younger, that wasn't the case due to him being the bullied one; as he got older, though...
  • The Bus Came Back: Last time he was seen, he got beaten in the first Sly game. He came back in Honor Among Thieves as a pilot for the Black Baron's dogfighting games, and again in the short cartoon "Timing is Everything."
  • Butt-Monkey:
    • Muggshot, while still a credible threat in combat, is easily the most ineffectual and unlucky Fiendish Five member. In Sly 1's "Sunset Snake Eyes," his casino scheme is barely turning a profit because he drove everyone out of Mesa City and orders his henchmen to shoot up any potential visitors due to a tip that a police officer is snooping around. He also got the short end of the stick regarding his share of the Thievius Raccoonus pages; he not only fails to understand his section, but he's unlikely to benefit from its teachings even if he could.
    • Later, in Sly 3's "Flight of Fancy," he's beaten up badly twice over. During his first bout, Murray repeatedly slams an engine block into Muggshot's chest. During the second encounter, Bentley gravely insults his mother to goad Muggshot into a fight, then tricks him into fighting Carmelita instead. She arrests Muggshot again, disqualifying him and his team from the ACES Competition.
  • Charles Atlas Superpower: When he was young, he was a normal pup. Fast-forward to adulthood after constant strength training, and he's a one-dog wrecking crew by just relying on his fists.
  • Cigar Chomper: Just look at the picture here.
  • Didn't Think This Through: His grand scheme for Mesa City was to drive out everyone living there to set up his gambling ring. Not just rival criminals or casinos, absolutely everyone in the city. Shortly after Mesa City becomes a ghost town, he realizes that this leaves no customers for his casinos.
  • Dumb Muscle: Shown punching through a bank's vault door in his introduction, but seems to have given up on getting smarter while beefing himself up. Muggshot is pretty stupid for being a mob boss.
    • His response to nobody being around to gamble (after he drove out everyone in Mesa City) has him announce to his goons that they should welcome anyone coming into town... only to then order them to greet any visitor with a hail of lead seconds later, since he received a "reliable" tip that a cop might be snooping around. The tip is right and is foreshadowing Carmelita's presence (again), but he's really hurting for cash after kicking everyone out of the city.
    • Also can't even pronounce "Thievius Raccoonus" and didn't care about his section of the book because it had too many words. He instead fights Sly since he's messing up his gambling operation.
    • Surprisingly, despite his low intelligence, he does know the words "transgressed" and "violated", refers to his opponents as "troglodytes", and he also knows what a "solar plexius" is.
  • Even Bad Men Love Their Mamas: Muggshot refuses to fight Bentley in Honor Among Thieves despite the turtle deliberately trying to rile him up. Insulting his mother proves to be the critical point for Bentley luring him into a fight in the town square.
  • Even Evil Has Standards: Even he is hesitant about attacking Bentley, who is confined to a wheelchair.
  • Freudian Excuse: He was picked on by other dogs as a child, leading him to take up gym lessons and adopt a personality like those of the gangsters in the Mafia films he so loved.
  • Guns Akimbo: With a pair of submachine guns, that are roughly the size of Sly's BODY.
  • Incredibly Lame Pun: One of the Mafia films he loves so much is called The Dogfather.
    • In Honour Among Thieves he reappears in Holland with his own team of pilots for the air races, thus making him a dogfighter.
  • I Shall Taunt You: In Sly 1 Muggshot has two taunts depending on how he interacts with Sly. If he successfully shoots Sly, Muggshot will proudly fire some rounds into the air. If Sly strikes him with his cane to no avail, Muggshot briefly stops what he's doing to laugh in Sly's face.
  • Jerkass: A big, tough, stupid gangster that loves to throw his weight around. A hot-tempered one at that.
  • Large and in Charge: The biggest member of his gang by far, and the top dog.
  • Made of Iron: He can't be hurt by Sly's cane or Murray's fists, and can take multiple shots to the "solar plexius" with an engine block without significant damage. It takes focused sunlight (in the first game) and multiple rounds from Carmelita's shock pistol (in the third game) to finally bring him down.
  • Power Fist: His arms and hands are so big that he uses them to walk.
  • Puzzle Boss: Muggshot's boss fights in the series all revolve around finding something capable of actually hurting the big lug since his massive muscles make melee weapons or punches simply bounce off Muggshot with no effect. You either have to use methods that outright bypass his defense (the aforementioned sunlight or shock pistol rounds) or hit him with something tougher than he is.
  • "Shaggy Dog" Story: Pun unintentional. He's somewhat miffed that his cut from the Thievius Raccoonus "heist" he committed with the rest of the Fiendish Five was a collection of pages that he had no real use for.
  • Top-Heavy Guy: His lower body is so small in comparison to his torso that he has to walk around on his knuckles. In the "Timing is Everything" shorts, however, his proportions are far more normal with usable legs.
  • Who's Laughing Now?: His introduction video depicts him beating the stuffing out of his childhood tormentors when they're all adults.

    Mz. Ruby
"See you in the next world, Sly Cooper!"
Voiced by: Presciliana Esparolini

A Cajun alligator, the chief mystic of the Fiendish Five, and an accomplished wielder of black magic, whose command of forces beyond this world allow her to break both the laws of man and nature. She is based in the deepest, darkest parts of the Haitian jungle. Before becoming a criminal, Mz. Ruby had no living friends because of her voodoo powers. The only friends she had were the spirits she would summon with her powers. As an adult, she used her powers on the people who shunned her.

  • All of the Other Reindeer: In her backstory, she was avoided by other children thanks to her love of dead things and voodoo, which most people are normally afraid of.
  • Dance Battler: More like Dance Caster. She forces you to play a Rhythm Game as her boss fight.
  • Dark Action Girl: The only female in the Fiendish Five.
  • Fat and Proud: If Mz. Ruby successfully attacks Sly, she excitedly, rapidly drums her belly before cheering; it's big enough to offer a decently deep sound when struck.
  • Fat Bitch: A rare female example. She's got quite a large gut. Being an alligator, that's saying something.
  • Foreshadowing: The first sequence at the start of "A Deadly Dance" subtly signals what the rest of the encounter will entail. She uses her magic to cause her hideout's crocodile skull entrance to repeatedly open and bite in time with the background music. And during her idle animation, shown prominently when she and Sly first exchange words, she appears to be dancing in place, as if mentally preparing herself for the rhythm game ahead of her. Sure enough, the same animation plays as she waits for Sly to complete his turn, and like her hideout entrance, she too dances in time with the music.
  • Freudian Excuse: Her Hollywood Voodoo background caused her to be avoided by other children, leading her to animate corpses for companionship.
  • "Get Back Here!" Boss: Sly is forced to approach Mz. Ruby through a gauntlet of spell barrages. When he hits her, she'll teleport a good distance away to repeat the process until she runs out of stamina.
  • Glass Cannon: She can put out multiple impressive barrages of magical spells from a great distance. To make up for this, Mz. Ruby has a glass jaw (in spite of her size) and can only take 4 hits before going down. Compare this to other bosses in the series, who can at least weather a beating before being defeated.
  • Half-Dressed Cartoon Animal: One of the few female examples. Wears a pink tank-top, but no pants. She probably can't find one pair in her size anyway.
  • Hollywood Voodoo: Embraces every voodoo magic trope in the book, but used it to rob banks and other crimes.
  • Jive Turkey: Speaks in a very sassy tone with colorful words. Much more understandable than other examples in the series.
  • Large and in Charge: She's almost as large as Mugshot, but she doesn't take advantage of it, going down pretty quickly for her size.
  • Never Smile at a Crocodile: She's a crocodile and a very dangerous woman!
  • Only One Name: "Madame Ruby". That's just about it.
  • Psychopathic Womanchild: Mz. Ruby's game of Voodoo Simon Says, in addition to being incredibly silly compared to its environment, implies that she has a childish sense of fair play. So long as Sly dodges her heavily-telegraphed spells during his approach, she effectively hands him a promised opportunity to strike, doing little to defend herself. She's clearly more focused on the game than her self-preservation, something compounded by her accompanying flock of dancing chickens during her first two phases. It's possibly justified, considering other kids wouldn't play with Mz. Ruby as a child and she grew up lonely.
  • Put on a Bus: Despite all the members of the Fiendish Five being sent to jail, she and Raleigh are the only ones not to be seen in any of the games outside the first. Got it slightly worse than Raleigh, seeing as she's never so much as referenced again.
  • Ritual Magic: Her magic is based entirely around this. When Sly shows up in Haiti to get his pages back, Mz. Ruby and her minions were performing a gigantic one to create a ghost army to invade and take over Mexico.
  • Squishy Wizard: She only takes around four hits before going down for good, but she fills in the boss fight by making you dodge her spells in tune to the music, at least in the PS2 version before you reach her.
  • Tail Slap: When finally fought face-to-face, she attacks by slamming her tail down on the ground to kick up a concussive shockwave.
  • Woobie, Destroyer of Worlds: Poor girl. She was treated as an outcast at a young age and turned evil growing up as a result. Now, she's serving a life sentence.

    The Panda King 
See Allies page

"Clockwerk is... superior!"
"Perfection has no age."
Voiced by: Kevin Blackton

The leader of the Fiendish Five, Clockwerk is a monstrous robotic owl of unknown origin. He turned himself into a robot in order to hunt down and destroy the Cooper family, his greatest rival. He is at least 3200 years old, showing up even in the earliest parts of the Thievius Raccoonus (Thieves in Time marks him as even older, as he's visible even in the background of the ice age level). He possessed an incredibly well-fortified hideout in the Krakarov Volcano in Russia, before being defeated by Sly and his parts sent to a museum in Cairo. But then the Klaww Gang stole his body parts and repurposed them for their criminal schemes. The Cooper Gang managed to steal these powerful components back, only to have them stolen by Jean Bison after the Lumberjack Games. From there, the parts were passed on to Arpeggio, which turned out to be part of an Evil Plan to not only acquire Clockwerk's powerful body for himself but also his immortality, all through a complex scheme involving the operations of the rest of the Klaww Gang. However, Neyla betrayed Arpeggio and took the Clockwerk frame for herself, dubbing herself "Clock-La" and engaging the Cooper Gang in battle. Clock-La was defeated, and Carmelita destroyed Clockwerk's Hate Chip, which caused his mechanical body to rust and to corrode into nothingness. However, while the threat of Clockwerk was presumably eliminated forever, victory came at a great cost; Bentley lost the use of his legs due to a crushing bite from Clock-La's beak, which was a serious blow to Murray's morale.

  • Arch-Enemy: Of the Cooper Clan as a whole.
  • Attack of the 50-Foot Whatever: Clockwerk is HUGE.
  • Badass Boast: Throws these out during the fight against him.
    "My skills are superior. My intellect is refined. My experience is greater."
  • Batman Gambit: His plan to lure Sly into the gas chamber in his volcano lair pretty much counted on Sly's willingness to risk his life to save Carmelita Fox.
  • Big Bad: Of the first game.
  • Bond Villain Stupidity: Subverted. When Sly walks into his death trap in the first game, Clockwerk immediately activates it, and then gloats as the poison gas starts taking effect.
  • The Cameo: He shows up in the background of every episode in Thieves in Time. What's more, is that there are two treasures you can find that reference him in some way, namely his eye and the Dragon's Claw, since the bottom has "Clockwerk was here" scratched into it.
  • Cartoonish Supervillainy: This might be one's first impression of him as you ride towards his lair. A padlocked, ominous door guarding his entrance? Check. A bunch of mindlessly obedient servants? Check. A death ray? Double-check. But then, as you progress through his levels, you will slowly discover that he has worked very, very, VERY hard to show you he means business.
  • Contemporary Caveman: If his cameo appearance in Sly 4's "Clan of the Cave Raccoon" is any indication, Clockwerk has existed since prehistoric times.
  • Continuity Nod: His cameo appearances in Sly 4 are evidence that he really has been after the Coopers for millennia.
  • Crazy-Prepared: His base in the first game. The security measures were extensive on their own, but just in case Sly got past them, Clockwerk set up a deadly trap — a gas chamber with Carmelita Fox trapped inside. It was pretty easy to tell that it was a trap, but Sly couldn't just leave Carmelita in there... which is exactly what Clockwerk was counting on.
    • And just in case Sly brought along a friend who was technically savvy enough to disable the gas, Clockwerk created a computer firewall system that would not be easy to hack through.
  • Creepy Monotone: He speaks with a grating, robotic voice that sounds almost eerily calm. However, there's always an undertone of menace in his words, which sometimes comes through in full. Take his incensed response to Sly's Kirk Summation in the first game:
    Clockwerk: Enough, Sly Cooper! It ends here!
  • Cruel Mercy: As he explained to Sly, he only spared Sly as a child when he stole the Thievius Raccoonus because he was convinced that the Cooper Clan was only as successful as they are because of it and wanted to show the world as such. Sly, of course, proves him wrong.
  • Cyborg: Just about the only organic part of him that's still left is his brain, if even that.
  • Death by Irony: He spent thousands of years forging himself into the ultimate anti-thief predator only to be undone by standard law enforcement equipment such as Carmelita's jetpack and her helicopter.
  • Determinator: He has lived thousands of years just to get his revenge on the Cooper Clan. Not to mention all the damage he takes during the battle, only to keep on coming.
  • Diabolus ex Nihilo: Beyond his feud with the Cooper family, not much is known about him.
  • The Dreaded: A subtle one for Sly. In the second game, Sly is vehemently opposed to the idea of Clockwerk's body becoming reassembled.
  • Enemy Rising Behind: His reveal at the end of the first game is majestically terrifying. Or, as Bentley puts it:
    Bentley: Sly! BEHIND YOU!
  • Energy Ball: Utilizes dark purple ones as his main attack in his first and third phases during the final battle of the first game. Notably, in the third phase, he doesn't so much as fire them directly at Sly, but sends them up in arcs that create electrified pillars beneath them to impede his progress over the lava.
  • Evil Cannot Comprehend Good: He sees having empathy for others as a weakness. See Lack of Empathy below.
    • Furthermore, he simply sees the Thievius Raccoonus as a means to an end: it itself is the treasure, and not the memories and legacies of the family that built it. When Sly points this out, Clockwerk gets...upset.
  • Evil Is Petty: He waged a personal war with one goddamn family for generations spanning millenia, all because he didn't like how successful they were.
  • Eye Beams: His reassembled body in the second game has this ability.
  • Family Extermination: Clockwerk has this as his overall goal. A massive owl that's thousands of years old, he so despises the Cooper family that he's gradually replaced his entire body with cybernetic parts just so he can keep tormenting them across the centuries. He's spent his immortal life trying to wipe out every single one of the raccoon thieves, and it's eventually revealed that the combination of his determination to massacre them and the sheer hatred in his heart have made him functionally immortal—he wants to kill the Coopers so badly that he can't die until he does.
  • The Ghost: How he's played up until you actually meet him in the first game. He doesn't have intercom banter with his henchmen, his levels immediately progress from one to the next (unlike the "hub" worlds of the other Fiendish Five members), and until Sly gets caught in the gas chamber, you don't even hear him speak. Then, at the very end, as you fly above the ruins of his death ray, you think everything is all good and — HOLY SHIT.
  • Greater-Scope Villain: Of the second game. He's the reason everything is happening but doesn't influence the plot directly.
  • Green-Eyed Monster: Nourishes on a "steady diet of jealousy and hate".
  • Guide Dang It!: Since his cameos in Thieves in Time can only be seen during specific jobs in each episode, finding them all can be very difficult.
  • He Who Must Not Be Seen: Up until the end of the first game, he remains a silhouette and is never seen directly. The same applies to his appearances in Thieves in Time since you can only see the "Mini-Clockwerks" watching you.
  • Hell Is That Noise: The sound of his wings flapping is powerful... and menacing. If you hear them, it's too late for you... especially if your name is Cooper.
  • Immortality Immorality: His immortality is fueled by The Power of Hate, and he's spent centuries hunting down and killing the Coopers.
  • Implacable Man: Considering that he survived a plunge into a volcano's molten crater and came rising up for round twonote , this trope applies.
    Bentley: Wow, that's one tough owl.
  • It's Personal: His vendetta against the Cooper line. For him to keep himself alive for centuries just to see it through, whatever sparked this rivalry in the first place had to be serious. Not to mention that murdering Sly's parents made it personal for Sly, as well...
  • Knight of Cerebus: The other members of the Fiendish Five have personality quirks, Freudian Excuses, and other subtle elements that lend a hint of comedy to them, villains though they may be. Not Clockwerk. He's a cold, ruthless, no-nonsense sociopath who speaks with a grating robotic voice, nearly kills Sly and Carmelita with a death trap, and generally comes across as much more serious and threatening than the rest of the Fiendish Five... to say nothing of many of the other villains in the series.
    • Even though he doesn't hijack the second game, he's still this since once his parts reassembled, it gets much darker and Neyla, after becoming one with his body, drops all comedic moments.
  • Lack of Empathy: It's not just that he lacks empathy, he identifies it as a weakness in others.
    "Sentimental fool! Empathy will always be the downfall of the Cooper Clan."
  • Large and in Charge: The leader of the Fiendish Five and by far the largest.
  • Laser-Guided Karma: Stole and divided the Thievius Raccoonus to make it difficult to reassemble. The same thing happens to his corpse in the second game.
  • Last Words: "COOPER! You will never be rid of me...! Clockwerk is... superior…!"
    • These might not seem like much, but think about the end of the second game. Even if Clockwerk's Hate Chip was destroyed, even if the reign of terror he's held over the Cooper Clan is finally over… he was directly responsible (well, technically Neyla) for Bentley's paralysis. So no matter what, whenever Sly sees his dear friend in a wheelchair, he will be reminded of that mechanical owl. Sly will never be rid of Clockwerk. From a Certain Point of View, The Bad Guy Wins.
  • MacGuffin: In the second game, various parts of his body are collected and used by the Klaww Gang to power their empire via spice trade. Sly's gang makes it their mission to prevent Clockwerk's body from becoming reassembled.
  • Mysterious Past: His backstory is never once elaborated on throughout the entire series. It makes him all the more menacing: he comes across less as a character and more of a force of evil.
  • Mysterious Watcher: His role in the fourth game. He appears in the background of various stages, doing nothing but watching. This is a Call-Back to the first game, where each picture of the thieves had his Silhouette in the picture.
  • New Powers as the Plot Demands: When his body is reassembled in the second game, it displays attacks he didn't have in the original.
    • This is most likely fridge brilliance: Arpeggio had planned to take control of the Clockwerk frame. No doubt he wasn't satisfied with the original model and intended a few more upgrades.
  • No Kill Like Overkill: When he finally tracked down Sly and his parents, he made sure he brought along four nigh-superpowered criminals to outnumber and gang up on his current rival.
  • No Name Given: If he had a name beyond "Clockwerk," it's never been shown.
  • No Nonsense Villain: Clockwerk does not fuck around.
  • Non-Standard Character Design: Contrasting with the cartoonish designs of the rest of the cast, and the artwork of him in cutscenes, in-game he looks like a more realistic depiction of an owl, albeit a mechanical one.
  • Noodle Incident: It is never stated why exactly he hates the Cooper Clan so much. We know he was jealous of their thieving ability, but something must have happened to amass a hatred this big...
  • Ominous Owl: He's a villainous cyborg owl. He's as ominous as you can get.
  • Paranoia Fuel: In-universe reputation, if your name is Cooper. This guy could suddenly crash in and kill you and your family at any moment, and the moment you actually heard his wings, it's already far too late — Sly's parents learned this the hard way.
    • In Sly Cooper — Thieves in Time, you can actually see him in the background. He also stalks you around the map. Remember, Clockwerk outright kills the majority of Sly's ancestors sooner or later. Who's to say he's not going to kill your ancestors again off-screen?
    • The cameos also add another layer when you consider that "Clockwerk" appears much smaller than he did originally and he is completely robotic in the Ice Age, which means that either he's back and has time travel or someone started making "Mini-Clockwerks" which only appear in the past because they are stalking Sly's gang.
  • Pass Throughthe Rings: Another one of his attacks from the first game (and one that Neyla retains as Clock-La) is to launch mechanical rings with electrified outer rims once he reaches his second phase. Sly must weave THROUGH the middle of the rings to evade the attack- if he doesn't, the rings will unleash an unavoidable wave of electricity from their sides.
  • The Pirates Who Don't Do Anything: Despite being described as a master thief, he's never shown to steal anything but Sly's cane, and that was through a minor minion.
  • Posthumous Character: Is firmly deceased throughout the second game, but his body parts are the main crux of the game's plot and the Cooper gang are collecting them specifically so Clockwerk can't be brought back to life.
  • The Power of Hate: Clockwerk is a firm believer in this. In fact, the second game revealed that it was a "Hate Chip" that served as the essential core for Clockwerk's immortality.
  • Purpose-Driven Immortality: Thanks to his "diet" and robotics, he has been able to stalk the Cooper Clan for centuries.
  • Red Eyes, Take Warning: He had those before turned himself into a cyborg. His new body had gold eyes, which flicker red when he speaks.
  • Red Herring: His appearances in Thieves in Time have nothing to do with the plot, simply serving as Easter Eggs to observant players.
  • Revenge: Has lived for centuries — perhaps even millennia — with the sole intention of taking vengeance on his rivals, the Cooper family line.
  • The Rival: To the Cooper family.
  • The Sociopath: See Lackof Empathy above.
  • Soul Jar: The Hate Chip is what keeps Clockwerk alive and even keeps all his parts pristine (being broken off into individual pieces notwithstanding). When it's destroyed at the end of Sly Cooper 2: Band of Thieves, the effect is immediate as all of Clockwerk's parts rust and corrode into trash before the gang's eyes.
  • Talking Animal: In a world of furries, this is all the more prominent because he resembles an ACTUAL owl.
  • Time Abyss: Evidently, Clockwerk is at least old enough to have been around during the Ice Age.
  • Tranquil Fury: Despite being stated to be literally fueled by hate, he's pretty calm and composed, even when confronting Sly.
  • Unknown Rival: The Sly Collection Official Strategy Guide reveals that, besides Sly and his father, very few Coopers even knew about Clockwerk's existence. The only one known to have interacted with him was Henriette Cooper.
    • This somewhat implies that he killed several members of the Cooper Clan, and was so effective that they never knew he was doing so.
    • However, the Thievius Raccoonus makes references to Clockwerk such as his wings being his symbol, his eyes being able to leave his victims transfixed and his talons being able to cut through steel. This implies that they did eventually come to learn about him over time.
  • Vile Villain, Saccharine Show: Oh yes. Not just for the first game, but for the entire series. The Sly Cooper series is a cartoonish, Lighter and Softer series than most. And though it has its dark moments, its villains are typically Laughably Evil, have some altruistic qualities, and some even reform. Clockwerk, however, is the exact opposite of every other villain in the series, as he has no redeemable qualities, is never played for comedy, and is for all intents and purposes, a Serial Killer played competently, completely, and horrifyingly straight in a kids game.
  • Virtue Is Weakness: He views the Coopers' empathy as a weakness to be exploited.
  • The Voiceless: Applies to him in the fourth game.
  • We Can Rebuild Him: The real point of the plot of Sly 2. Only this time, it wasn't HIM in control of the frame...
  • Wouldn't Hurt a Child: He states that the only reason why he didn't kill Sly when he was a kid is that he wanted Sly to either fail to become a thief or get himself killed trying to steal back the Thievius Raccoonus, as a way to prove to the world that, without the book, the Coopers were nothing.
  • You Killed My Father: Inverted. He's the one who murdered Sly's parents.
  • You Monster!: Invoked by Sly.
    Sly: Is it inappropriate to refer to him as a monster? No. Not at all.

Sly 2: Band of Thieves

    The Klaww Gang 

A group of five powerful crime lords and a powerful Interpol official from across the world, united for mutual profit, particularly through the spice trade. Tropes related to them:

  • Meaningful Background Event: All of them, sans Dimitri who at that point has been arrested, appear at Rajan's party in episode 2. Most of them only make appearances during the recon, though Jean Bison shares a bit of dialogue with Rajan.
  • Multinational Team: The members consist of a French iguana, two Indian tigers, a Czech spider, a Canadian bison and their leader is a British parrot.

    Dimitri Lousteau 
See Allies page.

"Come, face the might of Rajan, lord of these hills!"
Voiced by: David Scully

An Indian tiger spice lord who ships his spice to Jean Bison, and purchases an "ancestral palace" to further his pretension of royalty. He is, in actuality, a former Street Urchin who made it rich through drug smuggling. Even though he goes to great lengths to convince others of his "royalty", it's mostly to convince himself.

  • Aristocrats Are Evil: Given his obsession with putting on airs and seeming like a noble lord, Rajan gives this impression during "A Starry Eyed Encounter".
  • Believing Their Own Lies: As Sly puts it, his attempts to pass himself off as royalty are as much to convince himself as such as it is about convincing others.
  • Berserk Button: He hates being humiliated or getting wet.
  • Cats Are Mean: He's an evil tiger, and not the only one.
  • Cats Hate Water: Curiously enough Bentley notes that Rajan has an aversion to water despite being a tiger, the only species of feline that does not mind being wet.
  • Damage-Sponge Boss: Even though the player controls Murray for the fight, Rajan takes A LOT of damage before going down.
  • Evil Is Hammy: When he finally steps forward and challenges Sly, he isn't just Chewing the Scenery... he practically inhales it!
  • From Nobody to Nightmare: Went from from street rat to international drug lord.
  • Fatal Flaw: Wrath. Rajan's short temper was used against him by the Cooper Gang and Neyla to lure him out of the old temple, and he overreacts when they ruin his spice operations and flood the area.
  • Flunky Boss: Half of his boss fight is fending off his goons, and he tends to end up killing them by electrifying the water arena.
    Rajan: Defend your lord!
  • Getting High on Their Own Supply: During "The Predator Awakes", he can be heard (through a bug planted in his office) starting to use his own spice recreationally, and one of Bentley's briefings during the episode outright calls him "spice-addled". This likely contributes to how angry he gets during the episode's finale.
  • Heel–Face Turn: In the epilogue, he becomes a legitimate businessman and owns a rug business all across North America.
  • I Hate Past Me: He's ashamed of his past as a street rat and goes to great lengths to convince himself and others that he's actually Indian royalty.
  • Lean and Mean: Compared to his peers in the Klaww Gang, Rajan is noticeably thinner and taller.
  • Maniac Monkeys: His basic thugs.
  • Mundane Utility: While he uses the Clockwerk Heart fairly intelligently, he thought that the best way to exploit the high-tech, rare-alloy Clockwerk Wings was through simple (and gaudy) decoration for his palace's throne.
  • Nouveau Riche: Lives in a "newly purchased ancestral home" as part of his efforts to buy his way into respectability.
  • Old Shame: In-Universe, he's completely disgusted with his own homeless background.
  • Punctuated! For! Emphasis!: "Who's "The Murray"? All I see is a Fat. Pathetic. WEAKLING!"
  • Self-Made Man: Sly even calls him this while describing his background. In an interesting variation on the trope, Rajan is not proud of this fact in the slightest and goes to great lengths to hide his humble roots.
  • Shock and Awe: When it comes time to fight him, he uses half of Clockwerk's mechanical heart to generate streams of high-voltage energy.
  • Slasher Smile: His depiction for the 3rd episode depicts him with this, signaling his villainous breakdown.
  • Street Urchin: What he was during his childhood. He does not like to be reminded.
  • Underestimating Badassery: He dismisses Murray as a "fat, pathetic weakling," and gets his butt handed to him by Murray subsequently.
  • Villainous Breakdown: When the Cooper Gang floods his temple hideout, he comes charging out and starts Chewing the Scenery, hamming it up with such terms as "Black Clouds and Thunderbolts," "Clockwerk's Black Heart," and the Badass Boast: "This place is mine! *growls* Here, I am king!". Considering that the primary objective of Episode 3 is to aggravate him enough so that he comes out of hiding, this was fully intended.
    • Even before this, his embarrassing loss of the Clockwerk Wings, Carmelita's immediate arrest of several guests at his Ball, and being forced to flee his own palace completely breaks his composure.
  • "Where Are They Now?" Epilogue: Rajan served his prison sentence and became a rug and carpet merchant.

    The Contessa
"Oh, I'm sorry...was that an immoral act?"
Voiced by: Gloria Manon

A Slavic (likely Czechoslovakian) spider and senior Interpol official who is secretly brainwashing prisoners to make them lead a civilized life against their will...but only after they tell her the location of their loot so she can take it for herself.

  • Above Good and Evil: She practically quotes this trope verbatim when dismissing Sly's warnings regarding the Clockwerk Eyes. Sly, however, responds that, since she believes herself above morality, he's definitely not letting her have the Clockwerk Eyes.
  • Affably Evil: Hard to tell. She uses mocking politeness when "treating" her patients, but her respect for Sly after being beaten seems genuine.
  • American Gothic Couple: In her epilogue, a hypnotized couple in that pose and background is shown.
  • Arachnid Appearance and Attire: Well, she is a Spider-Taur and as it's hard to see the trademark red "hourglass" symbol of her species on her back having it as her belt buckle in addition to the web designs on her dress makes sense.
  • Aristocrats Are Evil: Subverted. She got her wealth and presumably her title by marriage, not by birth.
  • Bat Out of Hell: The basic minions for her levels.
  • Black Widow: She got her wealth from marrying an aristocrat, then poisoning his wine.
  • Dark Chick: She's less physically violent than her fellow teammates but her hypnotism's a far more invasive process towards her victims and her policies are particularly strict.
  • Deadpan Snarker: Particularly shown when Carmelita keeps vowing that "she'll get her" when trying to resist brainwashing.
  • Dirty Cop: An Interpol agent who uses hypnotherapy to get crooks to reveal their hidden loot so she can take it for herself and is part of the Klaww Gang.
  • Dirty Coward: Zigzagged. She won't go anywhere without bodyguards and she runs away from Carmelita, but she's willing to face Sly directly in battle.
  • Everyone Calls Him "Barkeep": Despite the likelihood of her title by her short-lived marriage we never learn of any other name for her, not even her husband's surname.
  • Giant Spider: A Black Widow spider fittingly enough, though as an interesting case her upper body's arms count as "legs" as her most spider-like portion only has 6 legs.
  • Gold Digger: Rather convenient her previous rich husband died soon after their wedding... or maybe it's simply because she's a black widow spider?
    • If one looks carefully during a cutscene, her husband's drink seems to be bubbling with...something...that the Contessa's drink doesn't have. It's heavily implied that she poisoned him.
  • Graceful Loser: When Sly beats her for the second time, she remarks that his mind is much stronger than she ever expected.
  • Heel–Face Turn: Subverted twice. She does it first as a Wounded Gazelle Gambit with Sly, and is shown to be hypnotizing real estate customers in the epilogue.
  • Hypnotic Eyes: Made even worse when she has the Clockwerk Eyes on her.
  • Hypocrite: She calls Sly Cooper's view of morality lopsided, yet she believes herself to be Above Good and Evil.
  • The Mole: Has been working for the Klaww Gang the whole time.
  • Non-Mammal Mammaries: A truly bizarre case all things considered, but it does suit her corset-topped outfits well.
  • Not-So-Well-Intentioned Extremist: She's introduced as a top member of Interpol who brainwashes criminals into reforming. It turns out that she really brainwashes them into revealing where they hide their loot, and she's been The Mole for the Klaww Gang the whole time.
  • Obviously Evil: She's a giant spider with red eyes who makes her homes in creepy Gothic buildings and employs nasty-looking bats, wolves, and vultures. Yet Interpol trusts her enough to give her a high-ranking position. Even Carmelita trusted her, being willing to let Neyla sit in on the prologue stakeout as "a favor to the Contessa." Of course, Carmelita loses the trust when she's betrayed by both Neyla and Contessa.
  • Opera Gloves: Fitting her aristocratic title she wears long gloves to complement her preference for low-cut sleeveless dresses in both her "casual" outfit and wedding dress, which also makes her upper body look more humanoid until you reach the claws which make up her "hands".
  • Praetorian Guard: Her Shadow Guards, who only show up in the background in the sixth level. According to Bentley, "Tough" is too wimpy a word for describing them. Of course, we never confront them directly, so there's no way of knowing for sure.
  • Red Eyes, Take Warning: Unusual for spiders but certainly emphasizes how Obviously Evil she is.
  • Rip Tailoring: Probably so the dress will fit over her Spider-Taur lower half.
  • The Shrink: Played with. She does seem to genuinely cure criminals but also makes them give up the location of their loot for her own gain. Bentley states that it was a particularly heinous crime, an insult to both thieves AND the law.
  • Spider People: An odd-looking case as being built more like a Spider-taur makes her upper body the most humanoid thing in-universe as everyone else is strictly a Funny Animal.
  • Suspiciously Similar Substitute: To Mz. Ruby, as a master of magic and voodoo and the sole female member (except for Neyla) of the Klaww Gang.
  • Tampering with Food and Drink: Presumably, this is how she killed her aristocratic husband. In the cutscene describing her backstory, the drink in said husband's hand bubbles as Bentley mentioned how he 'mysteriously died shortly after the honeymoon'.
  • Villain with Good Publicity: She's seen as a well-respected hypnotherapist until the Cooper Gang busts out of her prison and Neyla declares open war on her.
  • We Can Rule Together: She attempts this on Murray if it means retaking control over him for her hypnosis program. He rejects out of fury, citing the only help he needs is not to be reminded of her again.
  • "Where Are They Now?" Epilogue: The Contessa became a real estate agent, using her hypnosis to become successful.
  • Wounded Gazelle Gambit: She fakes a Heel–Face Turn to trick Sly into letting his guard down during her second boss fight. Sly doesn't believe her, but accidentally lets his guard down anyway.
  • You Gotta Have Blue Hair: Assumedly as a side effect of Hair Color Dissonance and how dark her level design is as her Black Widow lower body is in the same boat but an even lighter shade.

    Jean Bison
"Oh, it's tough being this tough. It sure is, yeah."
Voiced by: Ross Douglas

A Canadian Bison and former prospector and woodsman at the time of the Wild West. He was frozen in a freak avalanche for 100 years and unfrozen by global warming, bringing his Saruman-like aspirations of taming the wild north into the modern age.

  • Anti-Villain: He's often shown being A Father to His Men, and even Sly feels sorry for him given his Fish out of Temporal Water status.
  • Bad Boss: While normally a Benevolent Boss, he has shades of this in the lumberjack games, where he threatens his men acting as judges if they don't give him all perfect scores. (He even implies that he killed the previous judges)
  • Benevolent Boss: But unlike most of the villains in the series, he seems pretty nice to his men (besides the judges) and compliments them for their work, though when the Clockwerk parts in his possession were stolen, he states he had them punished according to the "Lumberjack's code."
  • Born in the Wrong Century: Technically, he was born in the right one, but after a century of cryogenic suspension, his efforts at taming the wilderness are no longer appreciated.
  • Blade on a Stick: His Simple Staff when the Clockwerk Talons are affixed to it.
  • The Brute: Serves as one for the Klaww Gang, but is smarter than other examples in the series. Bison is definitely a strong fighter when he has to be, but he's more of a threat due to his physical prowess instead of sheer muscle.
  • Canada, Eh?: Occasionally says "eh" at the end of his sentences, but otherwise averted. His own men play it more straight, though.
  • Fantastic Racism: Bison has a very low opinion of turtles, which he isn't afraid to share with Bentley.
    Jean-Bison: I wouldn't expect one of your kind to understand the finer points of commerce. You turtles are too stew-pid to know a woodcutter from a woodchuck!
    Bentley: That's it! Time I showed you just how "stew-pid" we turtles really are!
  • Fish out of Temporal Water: As Sly says, he's just a regular guy from the 19th century. He would have been a hero in his day for pushing the frontier forward, but in the modern-day, he's considered an ecological villain.
    • In the epilogue, he seems to have realized the full impact of deforestation, as he was seen working for the Environmental Protection Agency.
  • Flunky Boss
    Bison: Come on in here boys! Let's get this varmint.
  • Heel–Face Turn: In the epilogue, he's shown to be working for the Environmental Protection Agency. Sadly, he ends up frozen again when rescuing baby penguins in the arctic.
  • Hoist by His Own Petard: Bentley defeats him, thanks to Sly, by giving him commands on using Bison's own wood cutting equipment against him. Made all the more ironic because Jean Bison didn't believe that turtles were very bright.
  • Human Popsicle: Was buried in an avalanche and frozen during the Gold Rush of 1852, and thawed out in the present day thanks to global warming.
  • Karma Houdini: He's the only member of the Klaww Gang to escape being arrested or killed, as the Cooper Gang just leave him behind after defeating him, and he isn't mentioned in the following cutscene.
  • Large and in Charge: Much bigger and broader than his henchmen, and is more physically intimidating than the other Klaww Gang members as a result.
  • Puzzle Boss: Makes sense, given who you're playing as for the fight.
  • Sequential Boss: Every time you take out some of his health during his boss fight, he adds a new trick to his repertoire. First, he starts calling for his guards to help him out, then he starts throwing dynamite, and finally combines both of them.
  • Sore Loser: In the Lumberjack Games that he holds. Admittedly, he's very good at them, as Bison is legitimately the previous champion for the previous games; Bentley deduces that even with the Gang's preparations, it's literally impossible for the Cooper Gang to beat him without cheating. But he hates losing so much that not only does he hire the judges to make sure they give him the best scores, Bison also threatens them with bodily harm if they give him less than perfect ones. The Cooper Gang eventually has to lure the judges away to replace them in a desperate last move - but Bison sees through their disguise and knocks them out.
  • Species Surname: In his case, it is pronounced "Bih-Sawn".
  • Terra Deforming: Bison's ultimate goal is to tame the wilds of Canada by damming every river and deforesting every square acre of land he can get his hands on. He claims the Clockwerk Talons for their durability and cutting power, which would apparently let Bison cut down an entire forest in hours.
  • "Where Are They Now?" Epilogue: Jean Bison joined EPA, only to be frozen again when he saved a family of penguins.

"Oh, my poor naive meticulous mind has found a way."
Voiced by: Sam Mowry

A British parrot with great wealth and an enormous airship. The machinist of the Klaww Gang, and arguably its leader. Before becoming a criminal, Arpeggio went to a prestigious boarding school where he excelled mentally, but he suffered from a condition that left him with tiny wings and thus was unable to fly as his peers did. Angry at his weak body, he sought out Clockwerk's body for himself so he can not only fly but become immortal.

  • Affably Evil: When Sly confronts him at the end of the game, he's unfailingly polite to the master thief, and even admits that his plan to hypnotize Paris into a rage to empower Clockwerk's Hate Chip is rather cruel. Being a villain, of course, he dismisses this as "necessary."
  • Big Bad: Of the second game. Or so it would appear until Neyla took over.
  • Big Bad Wannabe: You would expect this parrot to be the main villain of Sly 2, him being the head honcho of Klaww Gang and trying to rebuild Clockwerk. Turns out, the real main villain is Neyla.
  • Cutscene Boss: Only appears in a cutscene and is never fought.
  • Cut Lex Luthor a Check: Considering Arpeggio is clearly rich enough to own a giant flying fortress, there is absolutely no reason that he couldn't have designed himself some sort of mecha-suit that allowed him to fly and be stronger.
  • Driven by Envy: Being bitterly envious towards other birds because of their ability to fly is a major reason behind his desire to use Clockwerk's parts to become immortal. Sly calls him on it.
    Sly: All this...because you can't fly. You're pathetic.
    Arpeggio: Immortality! Immortality is what I seek!
  • Evil Brit: Let's see: British accent? Check. Evil ambitions? Check. Rebuilding Clockwerk? Check. Yep, this man probably majored in Evil from the University of London.
  • Evil Is Petty: Again, as Sly's comment above points out, the whole reason that Arpeggio (most likely) masterminded the Interpol raid that stole the Clockwerk parts and nearly resurrected the "homicidal robot owl" note ? Because he wanted to fly.
  • Freudian Excuse: He was born a genius, but was never able to fly or keep up with the other students physically. This is part of the reason he seeks the Clockwerk frame, the other being immortality.
  • High-Class Glass: He's rocking a stylish monocle. Which is flung away when Clock-La crushes him; it ends up rolling over to Sly's feet.
  • Horrible Judge of Character: He's completely shocked when Neyla betrays him to take the Clockwerk frame for herself, apparently forgetting that she had double-crossed just about everyone else in the game already; Neyla even lampshades it.
  • Immortality Immorality: He's willing to go to some pretty heinous lengths in pursuit of Clockwerk's hatred-fueled immortality.
  • Killed Off for Real: He's crushed in Clock-La's beak, and is the only member of the Klaww Gang not to be mentioned in the "Where Are They Now?" Epilogue.
  • Know-Nothing Know-It-All: Though he is clearly brilliant when it comes to being book smart, he is actually rather poor at interpreting peoples' true intentions. Neyla played him like a fiddle.
  • Minor Major Character: His initial appearance is a non-speaking role at the party in Rajan's "ancestral palace", while his second and final appearance is a scene near the end of the game, where he reveals his master plan to hypnotize Paris using hypnotic lights devised by the Contessa and powered by Jean Bison's Northern Lights battery to send a Paris addled by spice sold by Dimitri, delivered by Jean Bison, and produced by Rajan into a hate frenzy, in order to make himself immortal and able to fly using the Clockwerk frame. However, he is betrayed by Neyla, and apparently dies soon afterward.
  • Non-Action Big Bad: Due to his physical weakness, he is obviously unable to engage in combat himself.
  • Only One Name: He was only addressed as "Mr. Arpeggio".
  • Too Clever by Half: He is clearly established as a brilliant mind, and he must have some degree of leadership to have brought such a disparate group as the Klaww Gang together. But he never considers the thought that Neyla would betray him, and this ends up killing him.
  • Too Dumb to Live: Besides the fact that he put his trust in someone who had betrayed literally every other person who thought she was an ally, when Neyla goes into the Clockwerk frame to merge with Clockwerk herself, Arpeggio yells that she's his only his protege and demands she exit the Clockwerk frame, apparently forgetting that Neyla is now a 30 foot long mechanical owl and gets crushed to death.
  • The Unfought: Only appears in cutscenes and is never fought.

    Constable Neyla
"No one likes to have their affections played with."
Voiced by: Alesia Glidewell

A wily Indian tigress who acquired a scholarship in England after being discovered to have set up a ring of her friends to do her work for her. A powerful opponent, with both strength and guile. In truth, she's Arpeggio's protégé and is helping him get all the Clockwerk parts, but only so she can betray him and take them for herself.

  • All There in the Manual: Her backstory is only revealed in the game’s instruction manual, which also makes note of her tendency for betrayal.
  • Bare Your Midriff: She is seen wearing a short top 2 times: on the job as a constable and when she was dancing with Sly.
  • Betty and Veronica: The "Veronica" to Carmelita's "Betty," with Sly being the "Archie" in this triangle.
  • Big Bad: Of the second game.
  • Body Horror: As a result of merging with Clockwerk, Neyla is reduced to some...ethereal...thing that is a mix of technology and organic. It's like looking at a demented hologram, and further proof that whatever humanity (for lack of a better way to put it) she once had is long gone.
  • Cats Are Mean: Nice at first, up until her thorough betrayal of the Cooper Gang and Carmelita. Just another evil tiger.
  • The Chessmaster: Manipulates all the different factions in the game throughout the game.
  • Chronic Backstabbing Disorder: Oh. Dear. Cthulhu. She betrays Interpol, Dimitri, Rajan, the Cooper Gang, Carmelita, the Contessa, and finally Arpeggio. In that order. When Arpeggio expresses amazement at Neyla's betrayal, her response is to be expected.
    Neyla: "Stupid Arpeggio. I double crossed the Cooper Gang, Interpol and Carmelita... what made you think I wouldn't do the same to you?"
  • Contrasting Sequel Antagonist: Neyla is a far more active antagonist compared to Clockwerk, not at all shy to go out in the field to get her hands dirty to further her goals. Whereas Clockwerk was already established as a villain due to being part of the Fiendish Five, Neyla initially comes off as a charming, friendly Interpol agent who is sympathetic towards Sly's goals and acts as a Friend on the Force to the Cooper Gang by helping them in their heists. This is before gradually revealing the nasty and traitorous individual she truly is, becoming more and more despicable by selling out Sly and Murray to Interpol, along with Carmelita by framing her for working with the gang the whole time to get Clockwerk's parts so she can get promoted, then turning out to be a mentee to the Klaww Gang's tech expert and de facto leader Arpeggio by helping him take down the Cooper Gang and the other members of the Klaww Gang to get at whatever Clockwerk parts they have so Arpeggio can reassemble Clockwerk, then stabbing Arpeggio in the back by knocking him down, jumping into the completed Clockwerk frame to become Clock-La, and crushing him to death with her beak once the merging process was complete. While little to no information of Clockwerk's background was revealed until the end of the first game, anyone who read the instruction manual for the second game would know that Neyla was once a penniless guttersnipe from New Delhi whose natural powers of persuasion allowed her to get into an exclusive British University where she conned classmates into doing schoolwork for her until the con was discovered and broken by the authorities, who were impressed enough to offer her a job at Interpol on the belief that she could win over any criminal she faced. Also, up until merging with the Clockwerk frame at the final stage of the game, Neyla is for the most part a Badass Normal who could give Sly a run for his money and needed little more than her wits and whip to get ahead in the game.
  • Dark Action Girl: She is more aggressive than Carmelita, in that she actually will attack anything in her way during the missions where she leads Sly (willing or while being chased) somewhere.
  • Dark Chick: Once she is proven to be a Klaww Gang member, her entire character suddenly turns to a good example of the trope.
  • Detective Mole: Neyla acts as this for the Klaww Gang, along with the Contessa.
  • Dirty Coward: During their final fight as Clock-La, she brags about her strength, but Sly writes her off as "The same coward we've beaten time and time again." Case in point, she always goes after the Clockwerk parts when she feels she has an advantage, like having a personal plane to fight Sly and Bentley with.
  • The Dragon: To Arpeggio, for as long as it suits her interests.
  • Dragon Ascendant: She becomes this after killing Arpeggio.
  • Dragon with an Agenda: She was most likely planning to betray Arpeggio and take Clockwerk's immortality for herself since the beggining.
  • Enigmatic Minion: Neyla seeks out Sly on her own in Paris to help him get into Dimitri's club, and is knowingly going behind Carmelita's back for no discernible reason. She keeps this up until India, where she drops the act to betray the Cooper Gang to Interpol. She continues to act as the long arm of the law throughout Prague and Canada, before revealing herself as the final member of the Klaww Gang aboard Arpeggio's blimp.
  • Evil Cannot Comprehend Good: Unfortunately, her attempts to insult Sly during "Operation: Choo-Choo" failed because of his brother-like friendship with Bentley and Murray.
  • Faux Affably Evil: She starts out friendly and sociable to the Cooper Gang, even helping Sly in his missions because she claims to understand the threat Clockwerk's parts pose. After double-crossing the Cooper Gang after they beat Rajan, she quickly reveals the true monster behind the mask.
  • Final Boss: At the end, she fused with Clockwerk and became Clock-La. Sly and the gang had quite a struggle with her, mainly because she stole their entire base! Also, she crippled Bentley.
  • Insult Backfire: Neyla tries to insult Sly during "Operation: Choo-Choo", but it backfires because of The Power of Friendship.
    Neyla: What's the problem Poodle? Afraid you can't take me on? Have to call up your little friends for help?
    Sly: (speaking into a transmitter) Come in "little friends", Neyla's got me pinned down.
  • Interpol Special Agent: Is assigned to work with Carmelita to pursue the Clockwerk Parts and to track down the most likely suspects, i.e. the Cooper Gang. She eventually betrays Interpol during "He Who Tames The Iron Horse".
  • It's All About Me: Neyla was noticed by adults in childhood through setting up her friends to do her work for her. And her conduct during the story makes it clear she's only after her own gain.
  • Jumping Off the Slippery Slope: After merging with Clockwerk, Neyla goes absolutely nuts.
  • Karmic Death: Her desire for immortality as Clock-La only leads to an early death. At the hands of the very Interpol Special Agent she betrayed back in India.
  • Killed Off for Real: She gets blown up along with Clockwerk's parts, and if she was still alive after that, she definitely wasn't after the Hate Chip was destroyed and the parts rusted into nothing.
  • Manipulative Bitch: A very fine example of this, seeing as once she drops the mask of Contessa's agent, she starts betraying absolutely everyone she can while being very smug about it.
  • One-Winged Angel: As Clock-La.
  • Private Military Contractors: She hires a mercenary army consisting of tanks and fighter planes to take down the Contessa. Possibly justified in that the Contessa had a private army of her own as well; she was likely matching force with force.
  • Reasonable Authority Figure: Compared to her partner, Neyla stands out for actually listening to Sly about his gang trying to stop a catastrophe from Clockwerk's parts being stolen. Only not so much.
  • Red Oni, Blue Oni: The blue oni to Carmelita's red oni.
  • The Rival: To Carmelita, both professionally and as a possible love interest for Sly. And after The Reveal, potentially to Sly in terms of acrobatic ability.
  • Small Role, Big Impact: Neyla only appears in the second game, and is killed at the very end. But as Clock-La, her last action is to crush Bentley in her beak as he is grabbing the Hate Chip, crippling him. This results in the trio's break-up, but eventually, leads to their reunion and the defeats of Don Octavio and the Mask of Dark Earth. Unfortunately for Bentley, his cripping leads to his ill-fated relationship with the sociopathic Penelope.
  • Split-Personality Takeover: Implied. Neyla is just as much of a sociopath as Clockwerk, but it seems like once she becomes Clock-La that some of Clockwerk's personality is starting to infect her own. She probably wouldn't have destroyed Sly regardless, but the sheer hatred she proclaims for him is very uncharacteristic of her. It's possible that if given time, Neyla's soul would've been merged with Clockwerk's.
  • The Starscream: She hijacks Arpeggio's plan for Clockwerk's body and France successfully and kills him (and all of his remaining mooks in the Final Battle).
  • Villain with Good Publicity: She's considered to be a well-respected Interpol officer until the very end of the game, even getting promoted to Captain after she sets up the Cooper Gang to be arrested, and framing Carmelita as being in league with them.
  • Villainous Breakdown: After her plane is shot down in Canada, and after being wounded as Clock-La by Carmelita and Sly. During the final portion of the Clock-La fight, she's pretty much snapped, screaming that she'll hunt Sly down and kill him in his sleep. There's also a nice little bit where she throws a tantrum after Sly steals back a Clockwerk Eye.
    Neyla: Don't you dare! That eye is MINE! IT'S MINE!
  • Walking Spoiler: This girl is full of surprises in the game, though her spot on this page lets her out of the bag.
  • Whip It Good: Her weapon of choice is a bullwhip, which she can use to fell enemies and set off nearby traps.

Sly 3: Honor Among Thieves

    Don Octavio
"This recital is over!"
Voiced by: David Scully

An Italian lion and former opera singer who was cast aside after rock and roll supplanted his career just as it was getting off the ground. While the new music took away most of his fame, Octavio retained fans in the Italian Mafia. They initiated the old singer into the business out of respect of his talent, with him rising to the position of Don. Octavio now runs a powerful Mafia operation in Venice, virtually controlling entire neighborhoods just based on his reputation.

  • Arc Villain: Octavio is this for "An Opera of Fear", though Carmelita briefly ups him during "Operation: Tar-Be Gone!".
  • Authority Equals Asskicking: His mafia controls all of Venice, and, despite his age, he's still able to go toe-to-toe with Murray.
  • The Bad Guy Wins: His plan to destroy a part of Venice still succeeded, regardless of the gangs' interference and the following defeat at Murray's hands. It nets him 30 years behind bars... but even then, he likely won't serve the full sentence due to dying from old age, and he now has a (literal) captive audience that appreciates his singing.
  • Berserk Button: Having something upstage him, which caused his Start of Darkness, or more subtly the new generations' childish and fickle tastes in entertainment (action and explosions), unfortunately, Murray presses the latter, and Octavio succeeds in his plan to destroy a large chunk of the city.)
  • Cats Are Mean: His basic minions are cats, and he himself is a lion, and not another tiger.
  • Cut His Heart Out with a Spoon: He has a rather… interesting threat when he briefly kidnaps Bentley.
    Octavio: Oh, I know all about you and your cracked little gang. You ain't nothing without this-a little guy's brains! So, I figure I just scoop 'em out real slow and use them to fertilize my tomato plants!
  • Evil Cannot Comprehend Good: He's baffled when he learns that the Cooper gang wasn't trying to stop him from blowing up Venice neighbourhoods to make a go for his territory or his life, but out of moral concerns.
  • Expy: His appearance is obviously a take on The Phantom of the Opera.
  • Fatal Flaw: Wrath. The several times he's encountered or heard, he's voicing his Hair-Trigger Temper-caliber anger on whatever's recently set him off, and he pulls no punches when he actually encounters Sly and Bentley. He technically succeeds in kidnapping Bentley in that he managed to return to his base with what he's taken, but then in a fit of anger throws it back at Sly, which stupidly returned a valuable asset to the Cooper Gang (all he needed to do at that point is walk inside his base and Sly would probably have severe issues getting the asset back). All that motivates him is anger he feels towards the changing times and trends that incidentally upstaged him. Even the first part of the big job portion of Venice is Bentley distracting him by openly competing with him in a Duet, making him angrily focus on the turtle and not notice Sly disconnecting the chandelier.
  • Freudian Excuse: If only rock and roll didn't prematurely end his opera career, he might not have fallen in with the mafia.
  • Hoist by His Own Petard: Without his tar pumping operation providing pools for him to get stuck in, he would have been almost guaranteed to defeat the Cooper Gang in a straight-up fight.
  • Ignored Epiphany: When Octavio is beat and caused to crash his boat in the motorboat driving segment, Sly tries to reason with him, demanding that he give them the detonation remote and they ALL make a break for it and avoid the cops. Octavio actually considers, and is about to cut his losses and accept his defeat gracefully when Murray lets loose a childish outburst of enthusiasm over the explosion from the boats crashing, angering Octavio enough to blow up several buildings.
  • Laser-Guided Karma: Almost as soon as he knocks Bentley down, he hits Murray's Berserk Button, and ass-kicking ensues.
  • Le Parkour: Even at his age, he's able to scale buildings with ease. And one of his attacks in the boss battle has him turning backflips.
  • Lightning Bruiser: Octavio is so fast and strong that Murray is only able to attack him when the ground is soaked with tar, which slows him down. Even then, the Don's only slightly slowed down by the stuff, it's more that Murray has actual openings with the tar involved.
  • Mad Artist: As an opera singer who's turned to villainy, this is a given.
  • Mad Bomber: He plans to threaten the whole of Venice with bombings unless they turn out to bear audience to his opera recitals.
  • The Mafia: They took him in after opera fell out of popularity, and now he's a high-ranking don.
  • Make Me Wanna Shout: The second part of his boss battle has him singing at you as a form of attack.
  • Nice Hat: Part of his operatic costume.
  • Only One Name: Only his last name is given to us; "Don" is just a title.
  • Panthera Awesome: He's a lion, people.
  • Politically Incorrect Villain: Has no qualms against kicking Bentley out of his wheelchair and mocking him while he's down. Unfortunately, he ends up hitting Murray's Berserk Button and getting his butt kicked in the process.
  • Smug Snake: The Don is very smug and confident when faced with threats during the episode, and it's not too hard to see why; he's in his home turf, he's got total control of the streets, and the local police can't even touch him on their own. Shame he doesn't take the Cooper Gang seriously.
  • Starter Villain: The first master criminal that Sly and Bentley run into while they're trying to rebuild the Cooper Gang by finding Murray. The Don's scheme is only a threat to Venice, but it could destroy the entire city.
  • Suspiciously Similar Substitute: To Rajan as a Wicked Cultured big cat that fights Murray.
  • Verbal Tic: Not him, but his voice actor. Tom Scully, who voiced Rajan in the previous game, snarls the same way when Octavio is making an announcement over an intercom.
  • Villain Ball: His plan to make opera popular again is, in contrast to the lucrative and mundane crimes that made him rich and powerful, as elaborate as it is insane. He even briefly acknowledges that it's a bit extreme during the boat battle with Sly and Murray, and is almost about to drop the ball before Murray sets him off.
  • Wake-Up Call Boss: Despite being the first boss of Sly 3, he is NOT an easy battle, and often trips up first time players of the game.
  • Wicked Cultured: Justified, what with him being an opera singer and all.

    Mask of Dark Earth
An ancient and evil spirit mask that can possess its victims, enlarging them and giving them super strength while giving the mask control over them.
  • Diabolus ex Nihilo: A perfect example of the trope. The Mask is never explained but is treated as an extremely dire threat by the Guru. It also gets destroyed at the end of "Rumble Down Under"
  • Dug Too Deep: The dingo miners unearthed this mask while searching for opals. It starts taking over various members of the digging operation.
  • Eldritch Abomination: There is no backstory for the Mask. Accordingly, we also have no idea how it became sentient and capable of making people into giants.
  • Floating Mask: When it doesn't have a host, it can float to get around.
  • Mask of Power: Whoever wears it becomes enormous and ballistic!
  • Recurring Boss: It is fought not once, but five times, two of which were indirect and the latter of which was unintentional.
  • The Unintelligible: Speaks through its wearers, but none of it is understandable, and unlike the Guru nobody understands what it's saying.

    The Black Baron
"Tonight, sleep like geese. And tomorrow, soar like eagles...high!"
Voiced by: Loren Hoskins

A master aviator who owns a castle in Holland, a whole town, and a whole stadium for dogfighting. He turns out to be an alias for Penelope.

Definitely not to be confused with THAT Black Baron.

  • Ace Pilot: A skilled pilot, though he relies a lot on his minions providing heavy fire.
  • Arc Villain: Of "Flight of Fancy", since Penelope challenges the Cooper Gang to defeat him in the ACES Championship for her to join the Gang's heist crew.
  • Badass Moustache: Subverted, as the moustache is only part of the disguise.
  • Everything's Messier with Pigs: Not really messy, but his pig henchmen use gasoline and wrenches.
  • Flunky Boss: Calls his men to assist when things look bad during the fight against him.
    "Earn your pay, you clods!"
  • Good Old Fisticuffs: He claims to have trained for ten years in fisticuffs just before he and Sly duke it out.
    "Pugilism is my passion!"
  • Hypocrite: He's introduced while giving a welcoming speech to the competitors of the ACES Dogfighting Championship, centered around the previous year's teams constantly sabotaging each other. The Baron ends the speech by angrily stating that the current Championship will be a fair competition. In spite of his anger at previous cheaters, the Baron has armed zeppelins waiting on his command to attack anyone who's likely to beat him in the dogfight finals and calls in some heavy backup (who also bring a huge replacement plane) when Sly blows him out of the sky.
  • Loophole Abuse: The Baron's reasoning for how he hasn't lost to Sly after landing on the giant plane mentioned above? He claims that since both he and Sly are still airborne, the victor has yet to be decided. This is after the declarations that if a competitor's biplane is destroyed, they are out of the Championship.
  • Killer Rabbit: OK, not literally, but his basic minions are rabbits with pitchforks (Fun Fact: They're a Palette Swap of Dimitri's rat goons from Sly 2).
    • And then made literal with revealing that Penelope is the boxing champion.
  • Red Baron: He's only known as the Black Baron, and explicitly set up the ACES tournaments to attract worthy opponents.
  • Samus Is a Girl: Penelope was stated as a repairman for the Baron until the disguise came off.
  • Token Human: The Baron's design doesn't resemble any sort of animal, looking more like an aviator version of Yosemite Sam.

    General Tsao
"Jing King is mine!"
Voiced by: Leo Chin

A northern Chinese rooster from an ancient line of powerful warlords, with command over dark magic. He aspires to merge his bloodline with the Panda King's through marrying his daughter, Jing King... despite the fact that she doesn't want to marry him.

  • 0% Approval Rating: None of his subjects are sad to see him go once he's arrested.
  • Arc Villain: Of "A Cold Alliance"
  • Authority Equals Asskicking: At least, that's what he believes. And he can back it up, as he's no slouch in a battle against Sly Cooper.
  • Black Magic: The vampires and the giant dragon Sly fights with.
  • Chinese Vampire: He summons a legion of praying mantises/"Hopping Vampires" that seem to be the equivalent of these.
  • Everything's Messier with Pigs: His basic thugs. Different from The Black Baron's own, in that they're dressed more elegantly and fight with martial arts instead of industrial tools.
  • Evil Cannot Comprehend Good: He believes that having obedient servants are better than having loved ones and friends.
  • Genius Bruiser: All his arrogant talk isn't just for show. He's a considerably skilled warrior coming from a long-line of warriors as well as a dangerous necromancer, and is deceptively clever. He was able to constantly outmaneuver Bentley and was the only Cooper villain to directly break into the Cooper Gang's hideout and steal their laptop to uncover their entire plan against him.
  • Half-Dressed Cartoon Animal: No pants.
  • Hate Sink: He is almost tailor-made to have a punchable face, especially compared to the more Laughably Evil and/or sympathetic villains in the rest of the game. He's a misogynist who forces Jing King to marry him against her will (with possible intentions of marital rape), he believes that having friends pales to having obedient servants, he unleashes a plague of Jiangshi on the populace as security and he kicked a puppy! Twice!
  • I Have You Now, My Pretty: Does this with Jing King. Not to mention his plan to forcibly merge their bloodlines means he had some heinous plans for her after the wedding.
  • It's All About Me: Tsao believes himself to be the most powerful warrior in the world and that everyone else is beneath him.
    Tsao: Why have friends when you can have servants? Why have love when you can have obedience?
  • Jerkass: Even Muggshot, who has a Freudian Excuse, a hesitancy to attack a crippled Bentley, and a soft spot for his mother, pales in comparison to him. Sly specifically tells him to his face that, out of all of the villains he's faced, Tsao is undoubtedly the worst.
    Tsao: Who needs friends when you can have servants? Who needs affection when you can have obedience? Ah, why try to convince you when I can simply destroy you.
  • Karmic Death: Well, more of a Karmic Arrest. Tsao looks down on women, as demonstrated with his treatment of Jing King. It's Carmelita, a female police officer, who ends up busting him. Poetic justice at its finest.
  • Kick the Dog:
    • Parodied during Bentley's initial slideshow in China. Bentley observes he saw him kick a puppy twice while he was under Bentley's surveillance.
    • Played straight regarding his "courtship" of Jing King. More specifically, he had her abducted from her home, then locked her in his palace and wouldn't let her out until the wedding night, despite her tearful pleas. When Sly points out that she doesn't want to marry him, well... see Politically Incorrect Villain.
    • And he also stole Bentley's computer without alerting the gang.
  • Knight of Cerebus: A surprising example as he's not the Big Bad. Very few moments with him have any humor, and even then they're mostly done to show how much of jerk he is.
  • Magic Knight: Leans more towards martial arts, but he can also cast a volley of fireballs, raise the arms of the dead to claw at his foes or summon ghostly dragon spirits.
  • Maniac Monkeys: His other basic minions. (Fun Fact: They're a Palette Swap of Rajan's back from Sly 2).
  • Obfuscating Stupidity: At first, he seems to be an idiot in a high position. It turns out he's much, much smarter than that. He actually saw through Sly's disguise, found the gang's hideout, and stole Bentley's computer. Bentley doesn't even realize it's missing until he's watching the slides of photos during the mission briefing...somehow.
  • One Steve Limit: Averted. There's a mook in Panda King's level in the first game also called General Tsao.
  • Politically Incorrect Villain: On Jing King's unwillingness to marry him: "She's a woman. She doesn't know up from down!" Sly later counters this by stating that "She's a person, not property."
  • Punny Name: His name is a pun on General Tso's chicken, a Chinese chicken dish. Appropriate, considering that Carmelita's Shock Pistol electrocutes him to medium-well.
  • Shadow Archetype: To Sly, He representing what Sly would become if he let his reputation and family legacy go to his head and looked down upon others because of it.
  • Smug Snake: A particularly nasty example thereof.
  • Stealth Pun: An insensitive individual who thinks very highly of himself? He's definitely a rooster.
  • Swiss Army Weapon: His weapon of choice is a combination of a shield and a circular buzz-saw.
  • Villain: Exit, Stage Left: He fights Sly on his own, and when he starts losing, he throws a smoke bomb at him and makes an escape.
  • Villain Respect: Unlike many who hate and fear the Panda King in his villainous days, Tsao regarded the Panda King as glorious and wished to marry his daughter just so he can merge their bloodlines to create an unstoppable dynasty.
  • Wire Fu: A duel between him and Sly features them leaping between bamboo shoots in this manner. Hand waved by Bentley as a manifestation of the "fighting energy" from past battles in the area.

    Captain LeFwee
"You've summed me up with but a word: Killer!"
Voiced by: David Scully

An arrogant and intelligent parrot of unknown origin, dubbing himself "The Smartest Man On The Seven Seas". Intriguingly, he appears to have a robotic arm with a sword. He is the most powerful pirate in all of Blood Bath Bay, a technologically backward archipelagic region known as the most lawless place on Earth.

  • Artificial Limbs: His leg and hand. The latter was also originally supposed to be a Swiss Army Appendage.
  • Bad Boss: His Establishing Character Moment is murdering his own Captain of the Guard simply for stating his own opinion.
  • Berserk Button: LeFwee hates it when his creativity is mocked, as shown when Sly chews him out for making him do the cliche of Walk the Plank.
  • Catchphrase: He really wants people to know that he's the Smartest Man On the Seven Seas. It's even his dying words as he's eaten by sharks.
  • Duel Boss: His boss fight is a one-on-one sword fight with Penelope, on the mast of his ship.
  • Eyepatch of Power: Despite having only one eye, he can handle himself in a sword fight.
  • Handicapped Badass: In spite of having a peg leg and a single eye, he's a capable fencer able to duel Penelope upon the mast of his ship without losing balance.
  • I Have You Now, My Pretty: To Penelope. Unlike Tsao, however, he at least admits he's far from the ideal courtier and compliments her before engaging her in a sword fight.
  • Kick the Dog: In his first appearance, he executes his own Captain of the Guard for being not alert enough to possible danger. While promoting his former second mate to the deceased Captain's position, he mentions he's off to the dungeon to torture his prisoners. Additionally, he attempted to chop Bentley's head off after he kicked him out of his wheelchair.
  • Laughably Evil: Despite being a rather bloodthirsty pirate, he DOES have some funny lines. When gloating about where he's keeping Penelope:
    LeFwee: "...and there she'll stay until she agrees to love me...despite all my faults."
  • A Pirate 400 Years Too Late: He and all of the residents of Blood Bath Bay.
  • Pirate: His entire profession. He raids ships and kidnaps women like a real pirate should.
  • Pirate Parrot: A more literal example of this trope.
  • Politically Incorrect Villain: A chauvinist pig and not above insulting and attacking a handicapped Bentley.
  • Real Men Wear Pink: His jacket, which is closer to magenta.
  • Small Role, Big Impact: LeFwee indirectly helped set up the events of Thieves in Time by kidnapping Penelope, causing her to fall for Bentley during "Operation: Reverse-Double Cross" when he helps rescue her. In turn, this results in Penelope betraying the Cooper Gang to Le Paradox because she wants Bentley for herself, which also causes that game's Downer Ending in Sly being trapped in Ancient Egypt.
  • Smug Snake: Oozes pride in his (respectable) intelligence and cunning at all times. Despite his smarts, he lacks the charisma and has too much arrogance and smugness to pull it off effectively.

    Dr. M
"Please! Keep your touchy-feely rhetoric to yourself, I can't stomach it! You Coopers are a bunch of dirty, attention-grubbing thieves! All of you, thieves!"
Voiced by: Rick May

A mandrill with a British accent who used to be The Smart Guy of the Cooper Gang, when Sly's father headed it. After Sly's father's death, he tried to claim the Cooper treasure as his own, spending decades trying to open it and building one of the most secure fortresses in the world on Kaine Island, in the South Pacific.

Unlike the Big Bads of the rest of the series, he has no connection to the villains in the rest of the game.

  • Big Bad: Of the third game. He's not actually connected to any of the other villains, but the entire game's plot is about breaking into Dr. M's near-impenetrable fortress.
  • Bad Boss: If the fact that he poisons one of his flunkies simply because he forgot to change the searchlight security password is anything to go by.
  • Contrasting Sequel Antagonist: Unlike the villains of the previous two games, Dr. M is a much more reclusive antagonist with no interest in leaving Kaine Island to commit any crimes or leading some international criminal group, focusing all of his efforts on cracking the Cooper Vault and maintaining his fortress while Sly and Bentley travel the globe to recruit more members for the gang to help them break into the vault, making him the villain with the least involvement in the game's main story. Additionally, while the game's prologue reveals his species, his significance to the plot as the main obstacle between the gang and the Cooper Vault, his aptitude in the fields of genetics and robotics, and his familiarity with the Cooper dynasty, it is not revealed what his beef with the Coopers is until the final stage of the game. At that point, Dr. M reveals he was a previous partner of Sly's father Connor back when he was alive and in charge of the Cooper gang, with Dr. M being the brains of the team similar to how Bentley is to Sly's group until he began to resent Connor due to feelings of being little more than a sidekick.
  • Crazy-Prepared: He has prepared for almost every eventuality to have the Cooper Vault for himself. He's built a fortress that covers practically every angle of approach, to the point that a direct assault is doomed to failure and that the default Cooper Gang simply cannot get around its various defenses without a highly coordinated group of specialists. He's also spent time and resources creating giant monsters that he can personally control, just in case someone tries to attack his lair.
  • Cutting the Knot: Trivializes all of the Cooper Vault's difficult internal security with a personal helicopter rig, flying through the platforming sections that Sly just went through the hard way.
  • Death by Materialism: He refused to abandon the Cooper fortune, even when the whole vault started collapsing in on his head. Presumably, he was either buried alive or crushed by falling stones.
  • Determinator: Despite getting all of the monsters he prepared beaten, losing a fight to Murray and Bentley, he still doesn't quit and runs into the vault, and doesn't even give up after his fight with Sly and Carmelita.
  • Entitled Bastard: Feels the Cooper fortune should be his, even though it rightfully belongs to Sly.
  • Establishing Character Moment: When we first see Dr. M, he's casually chatting with one of his guards, asking about the latter's family ...before just as casually mentioning that he poisoned said guard's drink for not changing the security code from 1-2-3.
  • Evil Brit: Speaks with an English accent.
  • Evil Counterpart: To Bentley. Like Bentley, he was the brains of the Cooper Gang (Sly's father's gang back in the day). But unlike Bentley, Dr. M defected from the group feeling unappreciated while Bentley stayed with his friends until the end, unappreciated or not.
  • Evil Former Friend: He was one of the partners of Sly's father in his heyday
  • Fallen Hero: He used to be the brains of the previous Cooper Gang.
  • Faux Affably Evil: In his first scene in the game's prologue, he calmly and politely chats with one of his guards and asks how his family is doing... before revealing that he poisoned the guard for forgetting to change the searchlight security password.
    Dr. M: Sorry, Richards, but I don't tolerate poor performance. You should have changed the security code from 1-2-3 after you installed the new system.
    Richards: I'll improve, I swear!
    Dr. M: No, you'll die. Any second now...
  • Genius Bruiser: Not only is he a genius scientist, but he's capable of grappling with Murray and bringing him to a standstill.
  • Green-Eyed Monster: He apparently turned evil because he felt marginalized out of his role in the previous Cooper Gang.
  • Hoist by His Own Petard: The various giant monsters and defensive measures that Dr. M spent decades developing cause the Cooper Vault to eventually cave in due to the various explosions that his fortress suffered during the heist. His obsession with the Vault means that Dr. M refused to leave the fortune within, even as the rocks began to fall.
  • Hypocrite: Calls the Cooper line out as selfish, despite ruthlessly trying to kill anybody who stands in his way of the pursuit of money.
  • Ignored Epiphany: Has a brief discussion with Sly near the end of his fight, and Sly manages to get M to acknowledge that Sly doesn't treat his Gang like Sly's father did when he and M were in the previous Cooper Gang. It almost looks for a moment that Dr. M might finally back down... but then Sly claims that he isn't like his ancestors, and that "touchy-feely rhetoric" enrages the ape past the boiling point.
  • Jerkass: He's an arrogant, condescending asshole who thinks he's better than everyone else due to his intelligence. He even kills one of his guards for simply forgetting to do one of his duties. Dr. M took it further by stating that the guard will never see his family again for his screw-up.
  • Made of Iron: Is still standing at the end of the game, despite a defeat from Bentley and Murray, which barely even phased him, and his fight with Sly and Carmelita. Instead, he does himself in.
  • Mad Scientist: Of both genetics, machines, and the combination of both.
  • Meaningful Name: Dr. Moreau anyone?
  • Noodle Incident: Whatever happened between Dr. M and Sly's father is never explained, and all that is known is that it was enough to cause Dr. M to split off from the Gang.
  • Not Me This Time: When he realizes that Sly learned about the Cooper Vault from Jim McSweeny, Sly assumes he set McSweeny up to have Sly go through the events of the game to try and break into the vault so he could follow him. Dr. M denies this, however, only revealing that he was part of the previous Cooper gang. There's no way of telling whether or not he's lying.
  • Not So Different: Implied to be the case with Bentley. But in the end, he becomes this to Penelope.
  • Omnidisciplinary Scientist: He's had a lot of time to develop his own biological technology, and experiment with creating big nasty monsters to fight off potential looters.
  • One-Letter Name: Dr. "M". 'Nuff said.
  • Orcus on His Throne: Justified. The Cooper Gang, chronologically, didn't even try to break into the vault until late in the game, and as far as the player knows, Dr. M wasn't even aware they were planning to. If he's truthful about the Not Me This Time above, this would make him the Big Bad with the least involvement in the main story in the series so far.
  • The Paranoiac: He's as intelligent as he is paranoid, refusing to let anyone even get near the impregnable door that leads his treasure. He built a fortress around the island housing the Cooper Vault with security as tight as Fort Knox (if not tighter) and kills his subordinates if they do not reset security passwords to his liking. He blatantly tried to kill Carmelita, a cop from Interpol, out of distrust when he could have legally claimed defensive action after Sly and his friends invaded the island that he legally owned after purchasing the deed to the location.
  • Playing with Syringes: Many of his minions seem to be combinations of different animals, and he commands three genetic monstrosities in his fights with the Cooper Gang.
  • Plug 'n' Play Technology: He has a giant plug in his head. It's how he controls his flying machine and the bigger monstrosities.
  • Recurring Boss: Unlike the final bosses of the first two games, you actually fight him SEVERAL times, each time in completely different circumstances, before he goes down for good.
  • The Smart Guy: Of the Cooper Gang back when Sly's father was running the show.
  • Villain Respect: As callous as he is towards Sly, Carmelita, and the other Cooper Gang members, he shows little hostility towards Bentley, who he regards as his intellectual equal. M even says that, since they are so alike, he has no reason to fight him.
  • Villainous Breakdown: In the ending, with the whole vault coming down, Dr. M starts screaming and pounding his chest, refusing to leave as it collapses. Before that, when Sly insists he's his own person and not just the latest in the Cooper line, Dr. M refuses to accept it, proclaiming him and his family to be nothing more than a bunch of attention-grubbing thieves. It's the way he delivers the line that showcases his last ounces of restraint slipping away.
  • We Have Reserves: Dr. M seems to literally create his own minions, which might be why he was so quick to kill his guard in the intro.
  • We Can Rule Together: Tries this on both Bentley and Dimitri. It doesn't work either time.
  • You Are Already Dead: During an elevator ride with the minion Richards, Dr. M admits he had Richards' drink poisoned at lunch since he failed to change the security code when they installed the new security systems.
    Richards: I'll improve, I swear!
    Dr. M: No, you'll die. Any second now.
    Richards: [gasps and expires]]
  • You Have Failed Me: He poisons one of his henchmen, Richards, for forgetting to enter in a new security code for the system of searchlights surrounding the Cooper Vault.

Sly Cooper: Thieves in Time

    El Jefe
Voiced by: Nolan North

El Jefe is a Cuban tiger that works as a highly-paid mercenary and conqueror. He is a ruthless dictator that can take over any land for a price and is assigned to take over territory in Feudal Japan.

  • Absurdly Sharp Blade: He's able to slice clean through multiple crane supports with his katanas.
  • Berserk Button: Sly mispronouncing his name as though it means "Big Baby" really ticks him off.
  • Breaking the Fourth Wall: El Jefe does the shush gesture at the screen just before he jumps Rioichi from above.
  • Cats Are Mean: Yet another evil tiger.
  • Cigar Chomper: Constantly smokes Cuban cigars.
  • Cigarette Burns: Before he fights Sly, he crushes his cigar into his own palm. Dude doesn't even blink. (Might have at least some fire resistance given his primary mode of attack?)
  • Cowardly Boss: He'll make you chase him across rooftops and various tall structures before giving you a chance to smack him around. But that doesn't mean that he can't fight...
  • Dual Wielding: He fights Sly with twin katanas.
  • Even Bad Men Love Their Mamas: El Jefe has a picture of his mother in his old hideout during the cutscene that explains his backstory.
  • Evil Counterpart: To the Panda King as a user of fire-based Supernatural Martial Arts, although the two never meet.
  • Fireballs: His primary means of attack.
  • The Generalissimo: He was a military dictator and mercenary leader before being recruited in Le Paradox's schemes.
  • Good Smoking, Evil Smoking: He chomps a Cuban cigar in his cutscenes...and grinds it out on his paw pad.
  • Gratuitous Spanish: The exclamation of "Estupido rata!" during the boss sequence... made more ironic with the incorrect grammar that was fixed (yet losing the trope) for the Spanish dub ("¡Estupida rata!").
  • Ironic Hell: After he is arrested, El Jefe does time rolling Cuban cigars... in a prison with a "No Smoking" policy.
  • Meaningful Name: It's Spanish for "The Boss".
  • Misplaced Wildlife: Sly and Bentley comment on how a tiger should be in a tropical jungle, not ancient Japan (not that Cuba actually has any wild tigers...).
  • Narcissist: He has a giant statue of himself built, and boasts that it's "almost as handsome as the real thing."
  • Neck Lift: If you get too close during his boss fight, he does this to Sly, then follows it up with an uppercut that takes out 1/3 of Sly's health bar.
  • No Celebrities Were Harmed: He's more or less Fidel Castro if Castro was a samurai tiger. His name (which means "The Boss") is even one of Castro's nicknames.
  • Not-So-Harmless Villain: He may spend most of his boss fight running from Sly, but when forced to fight, he holds his own quite well.
  • Panthera Awesome: He is a tiger, after all.
  • Playing with Fire: He can use friction to spark up his swords and create fireballs and flaming shockwaves.
  • Pungeon Master: When Sly's chasing him, he makes such cracks as "Feeling the heat?!" when hurling fireballs at Sly, and "How do you like my crane style?!" when cutting through the supports of a nearby crane to drop it on Sly (who actually stops to wonder if El Jefe's Incredibly Lame Puns are scarier than the man himself).
  • Shock and Awe: He can call down lightning to make his swords into electric BFSes.
  • Tennis Boss: As long as he's in a fighting stance, you can't get close enough to touch him with your cane (if you do, he'll Neck Lift Sly for an undodgeable 1/3 HP damage). You've got to stun him by using the samurai armor's shield to reflect his fireballs back at him before he's open to conventional attack.
  • Top-Heavy Guy: His arms are twice as thick as his legs.
  • "Where Are They Now?" Epilogue: He ended up in jail, where he was forced to handroll Cuban Cigars while being forbidden from smoking them himself (the prison had a "No Smoking' policy). Needless to say, he wasn't too happy about that.

Voiced by: David Lodge

An Eastern European armadillo, Toothpick is a small-time crook with an obsession with gold and western movies. Having grown up with an intense love of westerns, he channeled that into his criminal career in Eastern Europe, specializing in gold heists. Joining up with Le Paradox gave him the chance to live out his dream, becoming the corrupt sheriff on the town in which he captured Tennessee Kid Cooper, after swiping the gold that Tennessee had been planning on stealing and pinning the blame on him to add insult to injury.

  • Ascended Fanboy: He's a big fan of westerns. Now he gets to live in one.
  • Ax-Crazy: Sly acknowledges him as a "real loose cannon."
  • Bad Boss: When you make time off illegal and overtime mandatory, you know you're this trope. He's also prone to I Just Shot Marvin in the Face.
  • Batman Gambit: He puts a time-displaced Carmelita in danger to lure Sly and co. out of hiding and jail them.
  • Berserk Button: He REALLY hates whistling. It becomes an integral part of his boss battle, as Sly has to trigger the whistles on the train in order to lure him into the fighting arena.
  • Blow You Away: He can take off his hat and whip it around, sending a volley of whirlwinds spiraling at Sly during his boss battle.
  • Corrupt Hick: The marshall on a white horse, Sheriff Toothpick isn't.
  • Expy: Of Ren considering his demented appearance, Eastern European accent, and Ax-Crazy temper.
  • Gonk: Not the most handsome critter around.
  • Hulk Out: When he is upset or under stress, for some inexplicable reason.
  • I Just Shot Marvin in the Face: When Sly and Bentley bug his office, he accidentally shoots one of his flunkies, and when the other mook tells him to watch where he's aiming, he threatens him, only further cementing his Bad Boss status.
  • Jerkass: Not only is he a vain greedy slob, but he also enjoys overworking his minions. Even to the point that he made taking time off as illegal, and that overtime is now mandatory.
  • Killed Off for Real: On account of getting flattened by a train he didn't notice coming up the tracks, Toothpick is most certainly not coming back for an encore.
  • Large Ham: His voice is pretty loud whenever he's being excited and angry.
  • Laughably Evil: He's an arrogant, greedy, self-centered, violent ego-maniac, but any time these qualities are shown, he manages to make them hilarious.
  • Made of Iron: Getting trapped in a train's furnace (repeatedly) only seems to stun him. Then again, it does soften him up to the point where Sly's able to deal some serious damage with his cane. And even then, when he's charred by the train's furnace at the end, the only thing that hurts is his ears from the sound of the train whistle.
  • Narcissist: When you post pictures of yourself showing off all over town and throw a festival devoted to you, you definitely count.
  • Running Gag: By reading this far, you've probably noticed that Toothpick made time off illegal and overtime mandatory. In-game, this keeps getting broadcasted over the loudspeakers, and on this page, tropers love mentioning it.
  • Shell Backpack: Wears a white dress shirt and red vest, with the shell on his back visible.
  • Small Name, Big Ego: His egotistical posters in the Wild West, coupled with his insistence that his flunkies all celebrate his birthday (complete with gift-bringing), definitely points toward this.
  • Suspiciously Similar Substitute: To Muggshot, having the same backstory of being inspired by movies to take up a life of crime.
  • Sweet Tooth: Likes a special type of Cuban lollipops (which Bentley says it tastes like rice and beans).
  • There Is No Kill Like Overkill: Once he catches wind that the Cooper Gang is on his train stealing the gold back, he tells his guards to forget the 'alive' part in "wanted dead or alive", and says he wants them thrown off the train. Scratch that, he wants them blown to bits, shot, and then thrown off the train.
  • Trapped in the Past: His epilogue shows that unlike the other villains, he remains stuck in the Old West time, and gets put into a chain gang, goes deaf, and gets hit by a train that he didn't hear coming.
  • Villainous Breakdown: His PA messages during the final mission of the episode slowly get more and more crazy. By the time you reach him, he's pretty much snapped.
  • Weaksauce Weakness: He is particularly prone to high-pitched sounds such as whistles, which Sly uses to his advantage by repeatedly blowing the train's steam whistle.
  • "Where Are They Now?" Epilogue: Became part of a chain gang and was sent to working on railroads, eventually losing his hearing, which apparently led to his death because he couldn't hear a train coming while he was working on the track.
  • Wild West Armadillo: He's an armadillo working for the Big Bad, sent to terrorize the old Western town of Cotton Mouth Bluff. While there, he fits right in with the setting, toting guns and wearing a cowboy hat and a vest with a star badge, among other cowboy garbs.

    The Grizz
Voiced by: Fred Tatasciore

An American grizzly bear who was once a low-level thug. His graffiti tags soon brought him a brief period of wealth and fame in the art community, after his talent was recognized by a rising pop-artist. For a time, the art world praised his work as "Neo-Paleolithic Urban Expressionism." But, after a while, they slowly came around to the fact that his art was just plain bad, and that fall from stardom was what caused him to relapse into crime. With his anger to drive him, he became the most wanted art-thief on Interpol's radar. Teaming up with Le Paradox, he planned to reclaim his fortune by making paintings in the prehistoric past, hide them there, then dig them up again in the present.

  • 15 Minutes of Fame: He spent a brief time swiftly going from a common street thug to a universally recognized fine-artist. His equally swift fall from popularity left a big enough mark on him to become an art thief to get revenge on those that abandoned him, and Grizz eventually joins Le Paradox in a Time Travel for Fun and Profit scheme involving creating fake cave paintings when his 15 minutes ran out for good.
  • Acrofatic: He pulls off some skillful ice skating moves during his boss battle.
  • Alas, Poor Villain: Sly states that he feels sorry for the guy for the fact that Le Paradox is clearly just using him, and that he'll never actually be able to experience success in the art world again.
  • Bad Boss: He had a wooly-mammoth mook skinned as a coat for Le Paradox for failing a mission, he keeps a sabertooth tiger skin as decoration in his room and he pulled on a mammoth's tusks for the hell of it.
  • Bears Are Bad News: He's a grizzly bear and a real bad dude.
  • Calling Card: If his introductory cutscene is a big enough sign, he leaves his trademark stenciled tag wherever he commits a crime.
  • Cool Crown: It actually becomes a plot point, as it's what the gang uses to travel to Medieval England.
  • Even Evil Has Standards: He can't stand Le Paradox, who's a fellow art thief, going so far as to say "the best thing you can say about that guy is, he stinks!"
  • Evil Counterpart: To Dimitri, although the two never meet. Both are Mad Artists who talk in hip-hop slang with the Freudian Excuse of being rejected; Dimitri because the world wasn't ready for his Kinetic Aesthetic style despite being talented, while the Grizz's "Paleo-Urban Graffiti" style was hailed as innovative until people figured out he had no real skill backing him up. This even extends to their crimes, as Dimitri used his talent to make convincing counterfeits to show how tasteless the art world really was, while the Grizz just outright stole the work of more successful artists.
  • Generic Graffiti: Averted. The Grizz tends to leave a tag in his works.
  • Gratuitous Rap: The Grizz almost speaks entirely in impromptu rap.
  • Hidden Depths: Before his boss battle, he states that he has a love for ice skating.
  • An Ice Person: The Grizz gives off an ice aura that will freeze you if you get too close, and his shockwaves can freeze you as well.
  • I Just Want to Be Special: His pre-battle speech comes across as this, with him angrily stating that he's not going to let the Cooper Gang spoil his dream of being recognized for his art. The Ruby Crystal treasure states that the Grizz had them mined specifically to decorate his crown so that he could have a sense of self-worth.
  • Jive Turkey: Talks in a mix of hip-hop lingo and rapping. The latter often leads to him rhyming. Compared to Dimitri, however, he's much more comprehensible.
  • Large and in Charge: Even explicitly described as such in-game!
  • Mad Artist: When people learned that his art was just plain bad, he got revenge by becoming an art thief.
  • Mood Whiplash: Causes one just by being introduced. After beating Toothpick, the Cooper Gang and Carmelita have just become stranded in the Ice Age with possibly no chance of escaping pre-history... and then The Grizz is spotted during the recon mission; a giant black bear in a garish purple outfit, wearing a crown and speaking through rap.
  • Narcissist: While self-portraits are as old as antiquity in the fine-arts, the sheer amount of statues made in his likeness all over the level implies this, with the Ruby Crystal's description implying that it is all born from feelings of worthlessness.
  • One-Hit Wonder: In-Universe, it's what causes him to return to a life of crime.
  • Puzzle Boss: Unusually for a Murray boss, due to his various tricks keeping Murray from just punching his lights out.
  • Real Men Wear Pink: Putting aside that he wears a bright jumpsuit, The Grizz is a big black bear whose chosen career is being an artist, and his fondest childhood dream was to become an ice skater.
  • Rhymes on a Dime: He's quite fond of this ("It's gonna be nice, like sugar and spice, when I put that Cooper Gang on ice!").
  • Scary Black Man: Judging from his accent and dialect, he's apparently the Sly Cooper universe's equivalent of an African-American.
  • Stable Time Loop: A great subtle example; his plan to bury his art in the past goes off without being stopped by the Gangnote , so his art will eventually get uncovered in the present day. This leads to actual archaeologists finding it and making people think that it's the basis of "Neo-Paleolithic Urban Expressionism". After this, when The Grizz (as a low-class graffiti artist) is caught putting his tags on a wall, he's thought of as bringing back this ancient art style in a contemporary form; when people realize that he's just a bad artist and cast him away, he becomes involved with Paradox as a world-class art thief. After he gets sent to the Ice Age, the Grizz comes up the secondary goal of burying his art in the Ice Age for a large scale scam and is defeated before he can see it through.
  • Stout Strength: He's pretty tough for a guy with a bit of a paunch.
  • Spell My Name with a "The": "I'm The Grizz!"
  • The Starscream: Plans to betray Le Paradox after he's done with his part of the plan. He never gets the chance, though.
  • Terrible Artist: The Grizz only officially became an artist by pure accident, having been recognized as a potential artistic genius for his graffiti vandalism. However, it very quickly fell out of style as nothing more than a fad, Sly describing it as people realizing that his work is just bad and not a work of retro-nostalgia genius.
  • Time Travel for Fun and Profit: He creates paintings in the Ice Age that he can later dig up in the present day and sell for millions of dollars. While it's not stated specifically, there's also the distinct possibility it would make his present-day work popular again as well since suddenly there would be a "historical precedent" for it.
  • "Where Are They Now?" Epilogue: Works on his singing career in the jail and paints portraits of his fellow prisoners.

    The Black Knight (UNMARKED SPOILERS) 

Black Knight
"After I squash the Cooper Gang, I'll put them all in the circus!"
Voiced by: Annette Toutonghi

A mysterious armored figure, the Black Knight has brought advanced technology and robotics to Medieval England, working closely with Le Paradox. Penelope used this as a disguise to prevent the Cooper Gang from learning of her betrayal.

  • Black Knight: Quite literally.
  • Cut Lex Luthor a Check: When it's revealed that Penelope is the Knight, she muses to herself how she and Bentley could make billions designing weapons.
  • Fallen Hero: Turns out that it's Penelope behind the armor, much to Bentley's heartbreak and Sly's fury.
  • Gadgeteer Genius: Is revealed to be part of the reason Le Paradox can travel through time.
  • Humongous Mecha: The Black Knight's "Operation Overlord" turns out to be a giant robot.
  • Mini-Mecha: The Black Knight is actually an enclosed robotic suit that has just enough room for a small pilot to ride in. Penelope noticeably complains about how hot and cramped it is, though.
  • Samus Is a Girl: Turns out "he's" actually Penelope.
  • Tin Tyrant: As a black-armored knight who rules with an iron fist, this is inevitable.

Penelope Mouse

"Let's light this candle!"
Voiced by: Annette Toutonghi

A Dutch mouse, and an expert RC vehicle operator, mechanic, and pilot. She joins the team after being exposed as the Black Baron in the ACES Dogfighting Championship, an identity she had created due to age restrictions on dogfighting. Later became an Official Couple with Bentley, after being abducted by pirates, and saved his life during his attempt to rescue her.

In case you are wondering why she's on THIS page, sometime between the third and fourth games Penelope became greedy and was resentful of Sly's reputation while Bentley and she were nothing but support. She secretly teamed with Le Paradox to be the mole within the Cooper Gang, kicking off the plot of Thieves in Time by stealing Bentley's design for a time-travelling machine. Eventually, she disappeared to Bentley's worriment and was found in the medieval era donning yet another dark-armored persona, the Black Knight.

  • Action Girl: Penelope doesn't go for melee or being a good shot like others in the series, but her RC weapons level the playing field quite nicely.
    • Even without her tech, she shows some skills, particularly in pugilism as the Black Baron (she moves slow but hits hard) and fencing, though they don't come up often.
  • All Girls Want Bad Boys: When she first meets Bentley face-to-face, she is initially unimpressed (especially when his photo depicted him with muscles) and ends up showing an interest in more conventionally handsome Sly. It is not until Bentley saves her life in "Dead Men Tell No Tales" do they officially become a couple. In Thieves in Time, the attraction to Sly inverts entirely and she conspires against him when she thinks that he is holding Bentley back, their relationship falling out completely when Bentley refuses to betray the Cooper Gang for her.
  • All or Nothing: In Thieves in Time, Penelope gambled Bentley's loyalty to her and the billions of dollars they could make together for the lives of his two best friends. Needless to say, she lost horribly; she got kicked out of the Cooper Gang, Bentley hates her, and now she's friendless, broke, and on the run from Interpol.
  • Always Second Best: In the fourth game. While being intelligent enough to keep up with Bentley, it turns out Penelope's not quite the Omnidisciplinary Scientist she thinks she is as the Black Knight. Her creations are all giving her problems of some sort, and Bentley's observations place her work as adequate at best and sloppy at worst.
    • In the third, Bentley admits that his RC work is second-best to hers (though he does win out in other fields, as a Jack-of-All-Trades).
  • Ambition Is Evil: Penelope believes that Bentley could use his skills for greater means than simple thievery if it means becoming richer than the Cooper Vault could ever provide. But her idea of killing his friends to keep him to herself causes Bentley to see Penelope as nothing but a Gold Digger, and so he burned all of his bridges with her.
  • Arch-Enemy: By the end of the fourth game, Bentley and Penelope have become bitter enemies after their nasty breakup. She also becomes one of Sly's most hated enemies, both for breaking Bentley's heart and for trying to murder him out of jealousy; in the first mission, after her betrayal is revealed, Sly says that she is not their friend anymore in a hateful tone, and agrees with Galleth that she must be killed.
  • Arc Villain: Penelope is the main antagonist of both "Flight of Fancy" and "Of Mice and Mech".
  • Art Evolution: Penelope looks older and a bit less "cute" comparing her animation between the third and fourth games, which makes some sense as there's a gap in time between games, and she was originally banned from dogfighting due to being too young for that competition.
  • Beyond Redemption: Bentley has this conclusion when he defeats and nearly kills Penelope. All he could do was turn away in shame and leave her because she's a sociopath who used him, hates his friends, and rejected all of his attempts to redeem her.
  • Birds of a Feather: Played straight in the third game, but exploited and subverted on her part in Thieves in Time: she pretends to be like Bentley to win his trust and make a fortune with his designs, her real goal. She and Bentley bond over seeming to have many things in common: technological geniuses, apparently having similar interests, looking for love, etc. However when Penelope reveals her true colors, their similarities turn out to be either superficial or feigned on her part. Penelope ends up being Bentley's Evil Counterpart.
  • Break-Up Bonfire: Implied. After Bentley learns of her treason, the cutscene has Penelope toss a photo of him into the Hellfire behind her, all without any emotion on her face. It symbolizes that she has no remorse for betraying him, doesn't care for him one bit, and wants his friends dead so she can control him for profit. Bentley just vandalizes his photo of her instead of destroying it when their break-up is official.
  • Broken Pedestal: She used to have a crush on Sly, but not only did she eventually fall in love with Bentley instead, she also came to lose faith in Sly's "honorable thief" gig and eventually wants to kill him outright.
  • Characterization Marches On: During the third game, once her stint as the Black Baron is over, Penelope is depicted as being sweet, kind, considerate, and all-around good-natured. She goes out of her way to help the rest of the gang whenever they're in danger. However, once the fourth game rolls around, she is willing to sabotage the gang and even straight-up murder Sly and Murray out of resentment.
  • Camp Straight: She's a mechanic (an incredibly stereotypical job for a Butch Lesbian) and both of her disguises were as men, but she's only ever showed interest in Sly and Bentley. Also applies to her Black Knight persona, who is high-voiced and effeminate yet talks about Penelope in a clear I Have You Now, My Pretty vibe.
  • The Chick: The only female member of the Cooper Gang.
  • Chronic Backstabbing Disorder: Not as impressive as Neyla, but Penelope has betrayed both the Cooper Gang and Le Paradox for her selfish ambition. The Cooper Gang retaliate by leaving her in 1301 to die; it is not known how Le Paradox punished her.
  • Clingy Jealous Girl: Towards Bentley in Thieves in Time, with not even Sly or Murray safe from her jealous rage. This provides to be her undoing, leaving Penelope a Psycho Ex-Girlfriend.
  • Code Name: During the Cooper Vault job, she was "Agent Heartthrob".
  • Damsel in Distress:
    • When she is kidnapped by Captain LeFwee.
    • Also, her disappearance in the fourth game is what kicks off the plot. As it turns out...
  • Damsel out of Distress: She beats Captain LeFwee in a sword fight right after she is freed.
  • Deconstructed Character Archetype: Of the Lovable Rogue. Like the rest of the Cooper Gang she's a criminal who's portrayed positively and has unnamable traits like having people in her flying competition killed just so she could win or killing her henchmen. Unlike them, she shows such an individual won't turn out to be a Noble Demon that will stick with their True Companions thick and thin.
  • Defeat Means Friendship: Played straight and inverted. In the third game, Penelope willing joins the gang after Sly defeats her in a dogfighting match, and she fits in very well. However, her defeat in the fourth game ends with her and the Cooper Gang parting ways as enemies.
  • Didn't Think This Through: A technological genius Penelope may be, a thorough planner she is not, as her betrayal ultimately shows. To wit, her betrayal is founded on the idea that she and Bentley could make a fortune in weapons design if he wasn't held back by Sly's scruples, so she aligned herself with Le Paradox and provided him with the technology needed for his time-traveling caper while planning to double cross the skunk once he fulfilled his purpose, while at the same time planning to get Sly and Murray out of the picture so Bentley would be all hers. Once she reveals her motives to Bentley, however, he's quick to point out that by giving Le Paradox a functional time machine and the instructions on how to use it, she's also given him full control over the operation and no reason to think she's any less expendable than the other criminals he recruited for his scheme while also doing nothing to ensure Le Paradox will uphold his end of their deal instead of abandoning her in the past to die once she had fulfilled her role in his plot to steal the Cooper ancestor's canes, let alone come up with a contingency plan in case he does just that. Also, even if she had managed to get rid of Sly and Murray, Bentley would be inconsolable over the betrayal of the girl he loved and the loss of his two lifelong friends and surrogate brothers, and would have cut ties with her in a heartbeat upon learning what she did to them, possibly even selling her out to Interpol in revenge.
  • Disposable Fiancé: Well, Disposable Girlfriend.
  • Distaff Counterpart: To Dr. M at best, and to Clockwerk at worst. All three are sociopaths who are motivated by sheer hatred and envy to the Cooper family and their allies. Like Dr. M beforehand, Penelope's vendetta is mainly at the current member, in this case Sly, and shares his ruthless obsession with their goals. And like Clockwerk, as long as Penelope lives, she remains a serious threat to countless generations of the Cooper family because of her knowledge of time travel.
  • Evil Cannot Comprehend Good: In Thieves in Time. Similar to Neyla in the second game, Penelope cannot grasp how Bentley would willingly stay loyal to Sly and Murray in spite of the opportunities he has with her. So she plots to murder them both to have Bentley to herself, which backfires as Bentley points out that Penelope never even thought about how he would feel. This leaves her dumped and friendless.
  • Face–Heel Turn: She pulls one in Thieves in Time. She is, in fact, the true identity of the Black Knight, and is revealed to have been working with the Big Bad all along to destroy Sly, because she felt that she and Bentley were being held back by him from doing greater things and changing the world. Bentley ends up despising her — as evidenced by him later scribbling devil horns on the photo of her that he keeps in his Binocucom — and she ends up a disgraced criminal on the run.
  • Faked Kidnapping: The gang assume Le Paradox kidnapped Penelope, but in reality, she joined his side of her own free will, and allowed the gang to assume this.
  • Fallen Hero: Once a member of the Cooper Gang; as of Thieves in Time, she's one of their foes.
  • False Friend: She plans on killing her comrades in the Cooper Gang if it means getting Bentley's skills and making a profit.
  • False Soulmate: Penelope appeared to be Bentley's true love, but she's just a jealous, greedy, sociopathic scumbag who never loved him or cared about his feelings.
  • Fatal Flaw: Greed. She betrayed the Cooper Gang believing she and Bentley could use their genius to make a fortune without Sly holding them back, blinded to that Bentley values his camaraderie with Sly infinitely more than wealth. This costs Penelope her relationship with Bentley and leaves her with nothing.
  • Four Eyes, Zero Soul: She has the appearance of an adorable Meganekko, but in reality, Penelope is a highly selfish sociopath who desires nothing but money and power.
  • Gold Digger: Bentley suspects that this is the reason why Penelope opted to backstab his friends, as she wants his skills to make billions. This disgusts him and leads to their break-up.
  • Green-Eyed Monster: Penelope hates both Sly and Murray because she feels that they are holding back Bentley's full potential.
  • Heel–Face Revolving Door: Started off as a villain, then joins the gang following her defeat only to betray them later on.
  • History Repeats: A member of the Cooper Gang who's a technological genius deciding to go rogue because of growing resentment towards their leader? Yep, it looks like Sly now has his own Dr. M.
  • Humongous Mecha: She uses a bigger Black Knight mech in the first stage of her boss fight.
  • I Can Change My Beloved: Penelope believes she can change Bentley, but the way she intends to is borderline abusive and shows she's far too selfish to actually care about his feelings.
  • If I Can't Have You...: Penelope wanted Bentley to herself for his skills, and when he dumps her out of disgust of what she tried to do to Sly, she tries to murder him, too!
  • Irony: While not a stranger to deception and cheating, she and the Guru were the only members of the Cooper Gang without a criminal history before joining and had the experience and skills to make a sizable living legally in the private sector. Not only does she take to the criminal life like a fish to water, she winds up becoming one of the most ruthless members of the Cooper Gang and eventually betrays them for her own aspirations of ambition and profit.
  • Just Think of the Potential: Penelope sees a lot of potential with Bentley's skills, and wants to use it to profit from war and terrorism. Although he agrees about the potential, Bentley flat-out refuses to cooperate because of her lack of empathy. She then tries to destroy him to prevent his potential from being used elsewhere.
  • Karma Houdini: She is the only villain in Thieves in Time that manages to break out of jailnote  and resumes her activities. She continues to send Bentley postcards though, with it being ambiguous as to what they mean (apology mail, a warning of things to come, or a reminder to Bentley that she's still out in the world).
  • Kick the Dog: Penelope insults Bentley by calling him "dumb" while working on her plans to kill Sly and Murray, unaware that he's in the rafters and heard everything she said. When he finally confronts her, Bentley calls Penelope an "idiot" in retaliation.
  • Lack of Empathy: To Penelope, Bentley is merely a tool for her plans, and she responds to his heartfelt pleas with apathy. She also has the same feelings towards Le Paradox, intending to backstab him. And she's planning on selling weapons, not showing any care that billions could suffer or die from war because of her greed.
  • Legacy Character: It's implied at the end of Sly 3 that she and Bentley were going to continue the Cooper legacy themselves, or start their own (at the very least, they make their own Cooper-style vault). That all went out the window when Thieves in Time turned her into a Gold Digger.
  • Love-Interest Traitor: Thieves in Time sees her betray the Cooper gang and break Bentley's heart.
  • Love Makes You Evil: Averted. Penelope tells Bentley she betrayed him out of love, but he sees through the ruse, and correctly guesses that her betrayal was out of pure selfishness.
  • Meganekko: A cute, but psychopathic girl who is never seen without her glasses.
  • Mini-Mecha: The Black Knight armor.
  • Not So Similar: The third game presented her and Bentley as Birds of a Feather. But as revealed in the fourth game, they actually have nothing in common deep inside. Penelope is selfish, sociopathic, and desires to change the world for the worse while profiting from evil. Bentley is selfless, cares deeply for other people, is happy with his current status, and only uses his skills for personal gains. He was also able to overcome his resentment towards Sly, unlike Penelope, who allowed it to consume her heart.
  • Not-So-Well-Intentioned Extremist: She claims she betrayed the Cooper Gang to Le Paradox for Bentley's sake, as he's wasting his potential on them. But as Bentley himself points out, Penelope is actually a selfish Gold Digger, and a frozen-hearted sociopath masquerading as an Axe-Crazy yandere. She may claim everything she did was for Bentley, but in the end, Penelope is nothing more than a Classic Villain with no noble motivations, and just sees Bentley as a tool.
  • Odd Friendship: Penelope and Murray ended up forming a fledgling friendship during their mission in China. She helped save him and his van, and Murray was helpful to mentor and protect her during the main heist. Becomes heart breaking in hindsight, given what happened afterwards; now Murray wants to snap Penelope's neck for her trying to kill him and his friends.
  • Only in It for the Money: One half of her motivation for turning on the Cooper Gang in the fourth game. She wanted Bentley and her to change the world and to make a fortune on weapon dealing.
  • Pair the Smart Ones: A sad subversion. She shows more romantic interest in Sly, to begin with, and it's only after the Bloodbath Bay caper that she and Bentley officially became a couple. This becomes slightly less romantic in Thieves in Time, where Penelope reveals she only stuck with Bentley for the sheer potential profit that their partnership could have. It ends with a nasty breakup with the two hating each other.
  • Psychopathic Womanchild: Shows light shades of this, going even before her Face–Heel Turn. As the Black Baron, she cheated year after year to keep her top spot (probably costing the lives of at least some pilots who participated in her competition), which was entirely unnecessary considering all she needed was a disguise and skills to compete. As the Black Baron, one of her more dangerous attacks consists of stomping the wing of the plane in frustration, which can harm her employees (and though it goes unsaid, potentially damage the plane they were fighting on). Taken to 11 in 4 , shown through her occasional insults (even to Bentley), unwillingness to just talk things out with Bentley and willingness to hurt him emotionally and later physically, hypocrisy over her alignment with criminal groups, and blowing a raspberry at Sly when she prepares for her boss fight with her Humongous Mecha.
    • Paradox's "partners" imprison their respective Cooper ancestors in secure prisons: El Jefe puts Riochi in a cell over a bottomless pit, Toothpick imprisons Tennessee Kid in a maximum-security jail, etc. What did Penelope do with Sir Galleth? Put him in a giant circus rigged with deathtraps and repeatedly force Galleth to humiliate himself as the star attraction. It leads to Galleth hating her far more than Riochi and Tennessee hated their own captors.
  • Redemption Rejection: When he confronts her, Bentley tries to point out that Penelope has sided with someone who doesn't care about her intentions, and would just abandon her the minute she's outlived her usefulness. Penelope refuses to listen to him, just telling Bentley that their relationship is over and attacks him, showing she's crossed the line and will never give up in her quest for wealth and world domination.
  • Removing the Rival: She tries to get rid of Sly and Murray to have Bentley to herself. All three of them turn on her when they find out.
  • Rescue Romance: Seems to have a thing for them. While she was already interested in Sly before, her feelings increase after he rescues her from Tsao's dragon. Later she becomes a couple with Bentley after they perform a mutual rescue on each other.
  • The Resenter: In Thieves in Time. She comes to see Sly and Murray as holding her and Bentley back from intellectual greatness and decides to join with Le Paradox to have her revenge.
  • The Rival: To Bentley after "Of Mice and Mechs".
  • Romantic False Lead: Sly is one for her in Honor Among Thieves. Then she becomes one for Bentley in Thieves in Time.
  • Sadist: If some of her comments before and after The Reveal imply, Penelope enjoys the suffering and humiliation of other people. Asides forcing the proud Sir Galleth to be a circus display, she intends to make Sly a rug carpet, Murray a mounted trophy and the Gang's prized team van into a clown car.
  • The Smurfette Principle: Only girl in the Cooper Gang. At least until Sly 4...
  • The Sociopath: Penelope seems to be a Nice Girl, but when The Reveal is made, it's just as shocking to the players as it is to Bentley. She intends to use him to make a fortune in weapon designs, willing to profit from war and terrorism, having no empathy over the billions of people she's willing to endanger to satisfy her greed. Penelope never thought of Bentley as anything more than a tool, willing to control him for her plans by pretending to love him. Same with Le Paradox, thinking of him as a pawn in her goals despite the obvious contrary. She's also incapable of understanding genuine love and friendship, believing that Sly and Murray are holding Bentley back, when in reality, their friendship motivates Bentley and plays a role in who he is today. In all, Penelope is selfish, immoral, manipulative, and frozen-hearted who doesn't give anyone a damn.
  • Sixth Ranger Traitor: She is this to the Cooper gang in the fourth game.
  • Species Surname: She's a mouse who's last name is "Mouse". What did you expect?
  • Spy Catsuit: Switches from overalls to a jumpsuit in the fourth game.
  • Stuffed into the Fridge: In Thieves in Time. At first, it seems like she has been kidnapped to provide Bentley with a source of Angst. It turns out she's actually been turned evil to provide Bentley with a source of Angst.
  • Take Over the World: She wishes to conquer the world through weapon designing and the billions she can make through it.
  • They Were Holding You Back: Penelope feels this way towards Sly and Murray in regards to Bentley's skills, and is plotting to kill them both to have Bentley at his full potential, even if against his will. This disgusts Bentley, and convinces him that Penelope never loved him nor believed in The Power of Friendship.
  • Token Evil Teammate:
    • Among Sly's recruits in the third game are an old guru and two retired crime bosses who are aiding Sly out of gratitude for how he's recently helped them out. Penelope was running a dangerous and crooked biplane dogfighting scam, had no qualms about killing off underlings who were in the process of betraying her, attempted to murder Sly with her bare hands, and only joined the gang because she had promised to do so if they beat her "boss", i.e. beating her personally at her own game. It's little wonder that her loyalty to the Cooper Gang frays the way it does.
    • Oddly enough, this also applies to Le Paradox's group, despite them all being villains in the first place. The end goals of the other villains are limited to cigar smuggling, cave art forgery, hypnotism, and making themselves appear to be of French royalty. Penelope' end goals involve profiting from war and conquering the world.
  • Unexplained Accent: Despite being Dutch, she speaks with what seems to be a Minnesotan accent.
  • Ungrateful Bitch: Sly saves Penelope from the Stone Dragon in the third game. In the next, she is actively trying to kill him and is the sole reason why his entire family line is being wiped from history.
  • Using You All Along: Penelope failed to realize that she's merely a pawn for Le Paradox's actual goals and that she could be disposed of once he has Sir Galleth's cane. When Bentley points this out, she has a breakdown instead of the Heel Realization he hoped for.
  • Villain Has a Point: During her Motive Rant, she points out that Bentley could have done so much more in life than just been the brains of a group of thieves, given how unbelievably smart he is. She's absolutely right and Bentley agrees, but he loves his friends so much (they're practically family after all, considering they were all orphans and grew up together) that all he's ever wanted to be is part of their team.
  • Villainous Breakdown: Bentley finally realizes Penelope is Beyond Redemption when he can't get through to her. Unable to admit her own actions drove Bentley and his skills away and gave her powerful enemies as a consequence, Penelope snaps and attacks him.
  • Virtue Is Weakness: Considers the Cooper Gang's honor code to be pointless, and that she and Bentley could make much more money without it.
  • Walking Spoiler: Becomes one as of Thieves in Time. Seriously, the only thing you can say about her in that game is that she disappears at the beginning and Bentley is worried about her. Her spot on this page doesn't help the surprise, either.
  • War for Fun and Profit: Penelope wants Bentley to design weapons so she could sell them in the black market, presumably to terrorists.
  • We Can Rule Together: She offers this to Bentley when he confronts her about her betrayal in Thieves in Time. He refuses, refusing to become a villain like she did, and even calls her an idiot.
  • Western Terrorists: Implied case, given Penelope's intent to sell weapons in the black market and being tossed into a supermax prison somewhere in Europe, which normally holds the worst types of criminals.
  • "Where Are They Now?" Epilogue: She escapes prison, and ends up a homeless fugitive. Penelope continues to commit increasingly heinous crimes to this day, and sends postcards of them to Bentley to let him know she's after him.
  • Wrench Wench: Has RC skills that equal Bentley's own. She even helps Bentley reconstruct the Cooper Vault for future generations and builds the Time Machine that's used in Thieves in Time... then takes the blueprints for those and gives them to Le Paradox.
  • Wrong Guy First: When she first joins the gang, she has a massive crush on Sly that mostly serves to drive a wedge between him and Bentley. She soon decides that it's better to Pair the Smart Ones, since she has little in common with Sly. In the next game, Penelope becomes the Wrong Girl First to Bentley.
  • Yandere: Fourth game. Penelope wants Bentley all to herself and is willing to kill Sly and Murray for that reason. Then it becomes subverted; when Bentley dumps her, she tries to kill him, too, citing she'd rather have him dead than using his skills elsewhere.

    Miss Decibel 
Voiced by: Eliza Jane Schneider
" I will orchestrate your demise!"

A British Elephant, Miss Decibel came from a wealthy family and attempted to follow her passion for Classical music. Unfortunately due to her complete lack of musical talent, she was humiliated during her recital and during an explosive tantrum, she got a trumpet lodged into her nose. Thus she couldn’t play music...normally. Once she discovered she could hypnotize people with the unusual sounds, she began her new career path, hypnotizing and forcing others to commit crimes for her. Boss of the Arabian level and The Dragon to Le Paradox.

  • Acrofatic: During one section of her boss battle she can be lightning quick despite her immense size.
  • Alas, Poor Villain: Despite being a major antagonist, it's hard not to feel sorry for her, as when you finally confront her, she's just been on the receiving end of a major Dog-Kicking from Le Paradox. She fights you in a desperate attempt to prove she's still useful to him. Possibly why she pulls a Heel–Face Turn in the "Where Are They Now?" Epilogue.
  • Aristocrats Are Evil: Comes from a wealthy, respected family.
  • Berserk Button: While Giftedly Bad at playing it herself, Miss Decibel is a fan of Classical Music and can't stand any other genre of music, especially Rock & Roll. When Bentley creates a distraction by changing her music to Hard Rock, she goes into an Unstoppable Rage that gives Bentley time to plant a bug in her office.
    Decibel: My goodness, that awful screeching! It can't be... Rock and Roll! Aaaaagh! Must destroy!
    • She also hates anyone who criticizes her music or steals from her supply of peanut butter, especially as she's relying on that being shipped from the present.
  • Disability Superpower: A trumpet got lodged up her trunk that prevented her from playing normally (not that she was any good at it, to begin with), but somehow from the incident, she gained the ability to hypnotize people with soundwaves to do her bidding.
  • Distaff Counterpart: To Don Octavio as an Elegant Classical Musician who hates rock and roll and has sound-based powers.
  • The Dragon: To Le Paradox — she shares a more personal relationship with him than the rest of his gang or so she thinks, and was entrusted with the part of his master plan that would make him a member of France's royal family in the present day.
  • Dreadful Musician: In her backstory, which contributed to her turn to villainy. Listen to her with Bentley's bug and you'll find that she has caught her Mooks sneaking in earplugs at the recitals she makes them go to.
  • Evil Brit: As a member of British aristocracy and a criminal, this is kind of unavoidable.
  • Foil: To Don Octavio. Both of them are sophisticated older villains who utilize sound-based attacks and were originally in show business before becoming criminals and have a distinct abhorrence for rock n' roll. However, while Octavio was a genuinely talented opera singer who turned to villainy because more modern music genres like Rock music caused opera to go out of style, Decibel was a horribly untalented classical musician as a child who decided to turn to crime after a freak accident gave her the power to control victims through sound. Whereas Octavio commands the respect and loyalty of his underlings due to his position as a Mafia Don, Decibel is stated to be able to control people through auditory hypnosis from the tunes she plays from her trunk.
  • Hair-Trigger Temper: Has major anger problems due to being constantly ridiculed in the past.
  • Half-Dressed Cartoon Animal: An unusual female example; all she wears is her fur-trimmed long coat. As with Mz. Ruby, however, nothing explicit is shown.
    • She does have visible breasts, though, and her concept art gave her visible nipples.
  • Heel–Face Turn: In the credits, Ms. Decibel has the trumpet removed, takes anger management classes, teaches music lessons in prison, and is on her way to becoming eligible for parole for good behavior.
  • Informed Ability: Her introductory cutscene claims that she can use the horn in her trumpet to hypnotize others into committing crimes for her, yet we never see her do this in-game. Salim's gang are kept in an hypnotic state with sound-technology comparable to the Contessa's hypnosis technique, but that isn't the same thing and could have easily been built by Le Paradox or Penelope.
  • Interspecies Romance: With Le Paradox. Turns out that he's just using her, though.
  • Mad Artist: Technically, she's a Mad Musician, but the trope applies.
  • Mad Love: She's in love with Le Paradox, despite his blatant insinuation that he'll "be forced" to leave her stranded in ancient Arabia if she fails him. Sadly, it turns out he was just playing with her emotions and goes out of his way to mock her when she's no longer useful to him.
  • Meaningful Name: A decibel is a unit of sound measurement, and she uses a LOT of decibels in her screaming and attacking.
  • Musical Assassin: Can weaponize her music during her boss battle.
  • Not-So-Harmless Villain: She's surprisingly dangerous and competent when finally cornered.
  • Shock and Awe: Some of her weaponized music can shock you if you're not careful.
  • Trademark Favorite Food: Peanut Butter, according to the conversations you can listen in on after bugging her office.
  • "Where Are They Now?" Epilogue: While in jail she had the trumpet removed, began taking anger management classes and became a music teacher to the other inmates.

    Cyrille Le Paradox
Voiced by: Nolan North

A French skunk and leader of his own crime syndicate, Le Paradox poses to the public as a wealthy art collector. He is actually the descendant of a rival-but unsuccessful-family of thieves and seeks to steal the Cooper canes and ruin the Cooper family's reputation through time travel in order to have revenge on them because Sly's father indirectly caused Le Paradox's father to go to jail.

  • Avenging the Villain: Subverted. He does say he's avenging his father when first pressed by Sly on why he went after the Cooper family, but he doesn't really care that his father was sent to jail by Sly's father; he just wants to prove he's better than the Coopers.
  • Bad Boss: Once his "partners" get each of the Ancestors' canes, he just leaves them to either be arrested or trapped in their time.
    • In "Clan of the Cave Racoon", a guard mentions he yanked on one guy's tusk just For the Evulz. And in "40 Thieves", he threatens to have all of Miss Decibel's guards fired, and then executed if they failed to capture the Cooper gang.
  • Batman Gambit: Much like Clockwerk, he used Carmelita as bait to lure Sly into a trap, as he knows Sly will try to rescue her.
  • Big Bad: Of the fourth game.
  • Brilliant, but Lazy: What else can you call a guy who can plan heists worldwide through time and space, do none of the work, and take the bulk of the profit all without having it traced back to him?
  • Card-Carrying Villain: When Ms. Decibel calls him a "filthy, backstabbing, two-timing scoundrel", he responds with "Flattery will get you nowhere".
  • Chekhov's Gunman: In the prologue, Le Paradox, Ms. Decibel, and Toothpick can be seen as silhouettes through a window conversing with one another.
  • Clasp Your Hands If You Deceive: His hands tend to be in this stance during his appearances.
  • Classic Villain: Representing Ambition, Pride and Sloth.
  • The Collector: Fans even took to calling him The Collector before his real name was revealed.
  • Contrasting Sequel Antagonist: While both he and previous Big Bad Dr. M were bitter towards the glory of the Coopers, Dr. M was a hermit who worked independently from other villains. Le Paradox, however, masqueraded as a legitimate member of society and used others to do the dirty work for him. In the end, they both lost as a result of their own undoings, but while Dr. M was too caught up in his bitterness to leave the collapsing Cooper Vault and died, Le Paradox survived, but lost everything as a result of getting Sly caught up in his plans.
  • Cowardly Boss: The fight primarily consists of Sly chasing him through the blimp, but don't believe for a second that he can't fight.
  • Cut Lex Luthor a Check: He was already a wealthy and successful criminal in his own right, and he had a perfect cover operation to boot. Had he simply been content with that, the game would have never happened.
  • Cutscene Boss: His fight primarily consists of quick-time events, broken up by brief platforming segments.
  • Disney Villain Death: His defeat is set up like one as he pleads with Sly to save his life, only to steal his paraglider and escape. He then flies directly into a plane and plummets, but the trope is subverted when he's found in the River Seine and arrested.
  • Disproportionate Retribution: His whole plan was to erase the Cooper Family Line from existence. Why? Because he blames Sly's father for his own father's arrest (when he tried to frame Father Cooper for a theft he himself tried to commit), which lead to his own failing career as a criminal. That's a bit too much, don't you think?
    • Sly even points out how stupid this is. He had a great cover as a black market art collector in which he managed to amount a great fortune with no one the wiser, with skills he learned in prison that probably far surpass his father. Thus there was no need to go after the Cooper clan. He just did it because of his own ego and in the end it wound up costing him everything. Le Paradox himself even explicitly says that he doesn't really care about what happened to his dad; he just wants to prove he's better than the Coopers.
  • Everything Sounds Sexier in French: At least, according to Ms. Decibel...
  • Evil Counterpart: To Sly. He uses a very similar fighting style, and they both come from different lines of master thieves. His boss fight shows that he's capable of doing the Spire Jump and the Rail Slide.
  • Evil Is Petty: As Sly points out, he went after the Cooper line and exposed his operation to Sly because of his ego.
  • Foil: Like Sly, he's an agile and cunning rodent, a criminal genius who happens to be a master thief, descended from a long line of such thieves. However, where Sly is noble at his core, values his friends, and tries to do right by Carmelita, Le Paradox is an Insufferable Genius and Smug Snake who abandons his so-called "partners" when they're no longer of any use to him...including the woman who he supposedly loved.
  • Forehead of Doom: Have you seen his head? That thing is HUGE!
  • French Jerk: Though he'd probably be a jerk regardless of his nationality.
  • "Get Back Here!" Boss: Le Paradox runs after Sly deals significant damage to him.
  • Had to Come to Prison to Be a Crook: It was only after getting arrested that he gained the skills and connections necessary to become a successful criminal. He went in a two-bit crook with no talent or criminal skills, and came out a manipulator who could talk or bribe anyone into anything.
  • Hannibal Lecture: During his showdown with Sly, he boasts that having stolen the most precious possessions from the greatest thieves in history, he is now a better thief than the Cooper clan. Sly shuts him up, remarking that he went after the Coopers and exposed his operation out of sheer ego, and also remarking that he never did any of the actual stealing himself, instead of using his goons to steal the canes for him.
  • It's Personal: Blames the Cooper clan, and specifically, Sly's father for putting his own dad in jail and causing him to fumble in his own career as a master criminal in result.
  • I Have You Now, My Pretty: His kidnapping of Carmelita has some shades of this, especially when he's pointing out to Sly that she doesn't have any wings (he threatened to throw her off his blimp if Sly pursued him)...
  • It's All About Me: He doesn't care about anyone except himself, often ignoring his allies' requests for aid in their schemes... even though he expects them all to play their parts in ''his'' plan He doesn't even care that his father got arrested because of Sly's father. He just wanted to prove himself to be the greatest thief of all time.
  • I Surrender, Suckers: He manages to steal Sly's paraglider at the end of the game this way. Thankfully, karma kicks him pretty hard.
  • Jerkass: He's incredibly selfish, abandoning his own partners and stranding them in time once he'd used them as much as possible.
  • Kick the Dog: Especially regarding Ms. Decibel, who was in love with him. He even goes out of his way to mock her, pointing out that her music stinks, she's overweight, and that he already has Carmelita as his captive.
  • Laser-Guided Karma: After stealing Sly's paraglider at the end of the game, Le Paradox flies off while laughing condescendingly, until he crashes face-first into a passing airline plane. He loses the paraglider as a result and plummets into the Seine from miles high in the sky.
  • Moral Myopia: He fully expects all of his allies to aid him in his Evil Plan, but is openly treacherous and feels no obligation to help them in turn.
  • Narcissist: When the Gang returns to the present day, thanks to Le Paradox's alterations, the entire city is decorated with his face.
  • Non-Action Big Bad: As Sly points out, he never actually stole the Coopers' canes himself, instead of leaving it up to his goons to do so for him. That being said, when it comes to his final fight with Sly, he's no slouch.
  • Not-So-Harmless Villain: He doesn't seem like much, you say? Remember that this guy managed to build a vast criminal syndicate while posing as a law-abiding art collector, put together a cunning plan to use time travel as a means of achieving wealth and royal status, and can even fence with Sly on relatively equal terms. He can even do the Ninja Spire Jump and Rail Slide! And he's notable as the only Big Bad to actually survive a fight with Sly (if only by sheer dumb luck), a feat not even Clockwerk can claim. If it weren't for his massive ego and selfishness, he might well have gotten away with his scheme.
  • Pride Before a Fall: As pointed out by Sly, he ended up blowing his cover as a black market art dealer to both Sly's gang and Interpol because of his ego.
  • Revenge: His main motivation for going after the Cooper clan after Sly's father got his father arrested (although Sly's father didn't even know Le Paradox's father was after the same diamond and trying to frame him for the crime). Subverted, though, when he admits he didn't care about the grudge, he just wanted to prove he's the best thief ever.
  • The Rival: To the Cooper family, at least in the Le Paradox family's eyes. The Coopers most likely were not even aware of the Le Paradoxes' existence, since the latter just suck at thievery. You can blame their stink for that.
    • Case in point: Le Paradox's father was after the same diamond that cemented Sly's father's reputation as a master thief and tried to frame him for the crime. But Sly's father got to it first and Le Paradox's father got himself arrested.
  • Royal Rapier: His Weapon of Choice.
  • Sissy Villain: When he starts to lose, he begins to whine quite a bit. But if push comes to shove, Le Paradox will fight back.
  • Smelly Skunk: He even lampshades it himself. It's this trait that is the reason why the Le Paradoxes were not as successful as the Coopers when it came to thieving.
  • Smug Snake: He's a cunning mastermind who managed to establish an impressive criminal network while posing as an art collector, and his master plan to establish himself as French royalty is pretty clever. However, his massive ego and underestimation of his enemies prove to be his undoing.
  • The Sociopath: The guy checks off the major boxes. He cares only about himself, manipulates others into doing his work for him then tosses them aside like yesterday’s garbage once they’re of no more use to him, gets bored easily and gets very angry when things don’t go his way.
  • Stealth Insult: Anything that he says to Ms. Decibel.
  • Stupid Evil: As Sly points out, if he had just learned to control his pride, he would have gotten away with everything.
  • Time Travel for Fun and Profit: His master plan not counting revenge on the Cooper family line was to forge documents in the past that would establish him as a figure of royal ancestry in the present, allowing him to become the most wealthy and powerful figure in Europe.
  • Unknown Rival: The Le Paradox family is/was this collectively to the Cooper family. According to him, Le Paradoxes have been competing with the Cooper family for centuries... but they're never mentioned in the Thievius Raccoonus, and Sly's father never knew that Le Paradox's father was trying to steal the same gem that he was.
  • Using You All Along: It is unknown if Le Paradox was aware that one of his goons, Penelope, was using him all along, with the intent of backstabbing him, stealing his blueprints, and selling them for their own world domination ploy. Either way, Le Paradox got the upper hand when said goon has a breakdown, and he abandons them after getting what he needed.
  • Villain with Good Publicity: According to Carmelita, who didn't suspect his status as a criminal mastermind until she walked in on him loading black-market relics.
  • You Have Failed Me: He's not above simply stranding minions that have failed him in time. Or even when they do finish everything he asks of them...


    The Thugs, Goons, and Guards 
Voiced by: Various Actors

These are the guys who work for the various villains of the Games, attacking those who interfere. Usually, they are native species to the region where the villain they work for have set up shop. The first game had a large variety of guards for its levels, but as of the second game onward, there are two general types:

— Rooftop Guards, who patrol roofs, places aboveground, and mainly use melee attacks. These guys come in two types per level. They can chase intruders to high places.

— Flashlight Guards, who are larger than rooftop guards and patrol the ground with a light source of some sort that acts as their cone of awareness. These guards aren't able to get onto higher ground, but have greater strength, and have fast-shooting long-range firearms to make up for it, making them a great danger.

  • All There in the Manual: Flashlight Guards are called "Bouncers," and Rooftop Guards are "Swarmers" according to promo material and conceptual art, respectively.
  • Badass Normal: Most guards don't have powers, barring many from the first and some from the later games (like the pigs that work for General Tsao), and rely on skills with weapons to fight.
  • Bat Out of Hell: The Contessa has these as one type of rooftop guards.
  • Body Horror: One type of the Contessa's Werewolf guard constantly spits up spiders to attack you. And in the third game, Dr. M's genetic experiment guards in general speak for themselves.
  • Circling Birdies: Whenever you make a surprise hit on an enemy, or attack a rooftop guard as Murray, this is usually what happens. Though it's averted in the first installment (enemies disappear), and somewhat subverted in the forth as swirling lines, stars, and other symbols indicate them being knocked out.
  • Elite Mooks: The Flashlight Guards. Of the Cooper Gang core members, only Murray can beat them in an open fight without taking heavy damage.
  • From Nobody to Nightmare: The miner goons in Honor Among Thieves become more dangerous when possessed by the Mask of Dark Earth. Two of them are even fought as mini-bosses.
  • Gatling Good: In "Go West Young Raccoon" in Thieves in Time, every flashlight guard has an Old West gatling gun. They wield and fire it in one hand. Thankfully, they only use them to fire short bursts.
  • No Peripheral Vision: One of the best examples. You can stand right next to a guard or stand straight in their line of sight, and as long as you aren't touching them, or standing in their line of sight, they will never notice, even when the level is set in broad daylight.
  • Punch-Clock Villain: You can get the impression that at least some of the guards are only attempting to kill you because they are on duty. For example, in Thieves in Time, there is a guard in Medieval England that allows Sly to play a carnival game. The guard is in full "carnival host" mode during this time.
  • Ridiculously Human Robots: Two robotic guards in Thieves in Time have a conversation about "taking the kids to the beach."
  • The Smurfette Principle: Guard genders are predominantly male except for three. Nasty Charlotte (Mz. Ruby's spider guard) & Chow Mei (Panda King's kung-fu monkey guard) from Sly 1, and the dual saber-wielding Siamese cat guards in Ms. Decibel's level from Thieves in Time.
  • Strictly Formula: From the second game onwards. With the exception of the two toucan guard types in Arpeggio's level, all previous guards follow three specific types: Normal rooftop guards (Dimitri's rats, Rajan's monkeys, Contessa's wolves, Jean's ducks), rooftop guards that can send out an alert to other guards in the vicinity (Dimitri's frogs, Rajan's ibexes, Contessa's bats, Jean's goats), and the Flashlight Guards (Dimitri's boars, Rajan's rhinos, Contessa's vultures and Jean's moose), and even Arpeggio's goons are functionally Flashlight Guards and Short Guards. The third game featured a bit more variety.
  • Took a Level in Dumbass: Flashlight Guards were actually pretty competent in the first game, to the point where being spotted by one would lead to instant death more often than not. The developer commentary even refers to them as "smart guards". Starting with Band of Thieves, they suffer from No Peripheral Vision, their projectiles are incredibly inaccurate, and can easily be outrun, and they're constantly depicted in-universe as Dumb Muscle.
  • Uncertain Doom: All of the goons working for Arpeggio were presumably killed when Clock-La destroys the blimp carrying them during her breakdown, leaving the Cooper Gang as the Sole Survivors.
  • Underground Monkey: The shorter rooftop guards in the second game are all skin swaps of each other, sharing the same set of three-hit-combo, call-for-backup, and throwable-laser-bug attacks (the taller variants are unique to each level though).
  • You All Look Familiar: To be expected given technical limits, but taken to extremes with Arpeggio's guards, who are all exactly the same (even the flashlight guards only differ in that they have a mech suit).


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