Sam is one-half of the titular Freelance Police and is depicted as a six-foot tall anthropomorphic dog in a Film Noir-styled suit and fedora. He tends to come off as more level-headed and less violent than his partner Max, but not by much. He's passionate about justice, heavy weaponry, and bluegrass; and, to a lesser extent, popsicles, although he's self-conscious about his weight. He retains a mostly laid-back personality, except for his enthusiasm for his warped sense of justice. Max is usually the only thing keeping him from taking his "job" too seriously.
Although most of the time he acts like a human in a dog costume, Sam sometimes behaves like a dog, sticking his head out the window, whining, growling, or enjoying dog treats. He was born March 3rd, presumably sometime in the 1970's, and has been best friends with Max ever since they were children. Since then, they'be been inseparable, living and working together. He wields a Hand Cannon revolver, which he's quick to use, despite having terrible aim, or the fact he doesn't know what the word "aim" even means.
- Adaptational Heroism: Downplayed, but his Comedic Sociopathy is reduced in the games compared to in the comics and cartoon. This is likely done to make him, the Player Character, more of an Audience Surrogate.
- Adorkable: He may be the more sane of the duo, but he still has his fair share of quirks. He was a total computer geek in his youth; he even built Bluster Blaster!
- Ambiguously Bi: In "The Penal Zone," when you find a wedding ring, you can use it on Max and he'll imagine proposing to him. Sam decides not to do it, but you can also use it on an obviously male gorilla guard and he'll actually get through most of the proposal before being shot down.
- Additionally, in Poker Night 2 when asked about his relationship status, he will say that he is "off the market" confidentially. Seeing as how all of the females in his day-to-day life are either taken or uninterested, Max is the only logical candidate for this.
- He's seemingly excited when he hears there's going to be a stripper at Golem Lincoln's bachelor's party... which turns to shock and dismay when the stripper turns out to be Jurgen's Monster.
- In the comics, when Max is kidnapped as a sacrifice by a bunch of volcano god cultists, he gets very interested in the prospect of nubile cultist women and has to force himself to remember Max's dilemma.
- Barefoot Cartoon Animal: He wears no shoes at all. This gets used for a couple of jokes in "They Stole Max's Brain!", when Sammun-mak bans, then admires aglets, the little plastic things at the end of shoelaces.
- Bear Hug: When he's feeling affectionate towards Max, he will pull him into one.
- Berserk Button: Several, including calling him McGruff, calling him fat, trying to give him pink bellies, and especially trying to harm Max. He nearly shoots a kid who calls him fat despite said kid being his past self.
- Beware the Nice Ones: Sam can be pretty scary when someone presses one of his Berserk Buttons. Max is usually the only one who can calm him down. Between the laid back giant dog with a sweet tooth and the cheerfully violent hyperkinetic rabbit-thing, it's telling that the latter is the Morality Chain.
- In Episode 303 of the Telltale Games series, "They Stole Max's Brain!", we learn Sam doesn't look too kindly on people who steal his best friend's brain. It not only presses one of his Berserk Buttons in an epic way, but also means Max is not here to calm him down. On the plus side, we get to see Sam parody gritty film-noir detectives (such as Flint Paper).
- Big Friendly Dog: Meets all three criteria on average, but definitely not all three all the time. Also, kind of touchy about the "big" part.
- Catchphrase: Several, including:
- "You crack me up, little buddy!"
- "Well, here we are in/on/at [name of location]..."
- "Holy/Sweet [elaborate nonsequitur]!"
- Despair Event Horizon: In "The City That Dares Not Sleep", losing Max for real. He is completely silent and wanders aimlessly through the city, hugging himself and looking like he's going to cry.
- Expospeak Gag: Sam will nearly always say something elaborate and overly erudite as opposed to simple. Amusingly complicated phrases, sometimes having Max lampshade it, are the cornerstone of his wordplay.
- Expansion Pack Past: Occasionally he will remember when he did some sort of job after getting out High School and before become Freelance Police. For example, he was a circus acrobat, a cranny plumber and...a monkey. He also apparently went to flight stewardess school, which is why he sometimes offers people warm towels or pillows during interrogations.
- Extreme Omnivore: Max is just a regular junk-food hoarding Big Eater, but Sam is definitely one of these. Just listen to one of his pizza orders.
- Finger Gun: His favorite gesture when he is not actually holding a gun.
- Furry Reminder: When he finds a chocolate bar in Max's inventory in "The City That Dares Not Sleep", he remarks that Max had been trying to poison him. Thankfully, he's been eating enough fudge bars to build up an immunity to chocolate.
- Guest Fighter: One of the opposing players in Poker Night 2.
- Hand Cannon Revolver: His Weapon of Choice, complete with Infinite Ammo.
- Hates Being Touched: The only person that he lets touch him is Max.
- Heartbroken Badass: Noir Sam from "They Stole Max's Brain!" is basically a parody of this: He's not only imitating resident badass Flint Paper, he also has an option in the interrogation wheel to go into rambling speeches.
- Heroic BSoD: "The City That Dares Not Sleep"'s ending credits are nothing but him walking alone through the city towards the harbor, a stunned expression on his face as the Lonely Piano Piece does its thing.
- Heroic Comedic Sociopath: However, compared to Max, he can pass for normal. The games make him even milder, due to his position as the Player Character. He still counts, though, as someone who cheerfully inflicts pain and suffering for mild amusement, or simply because it's the most convenient way to deal with a problem.
- Hollywood Tone-Deaf: He howls his songs.
- I Call It "Vera": His Hand Cannon is called "Betsy" in the comics. It's never called by name in the Telltale games, but Team Fortress 2 calls it the "Big Kill".
- Immune to Mind Control: In the games by Telltale Games, Sam has a hypnosis-blocking device built into his hat from the end of "Culture Shock" on.
- Jerkass: Even though he and Max are best friends, he seems to abuse him quite often when rushing for the phone or just out of the blue. But who knows, Max probably enjoys it. He also busted the tail light on some random and unfortunate driver's car, pulled him over and fined him $10,000 for driving with a broken tail light that Sam caused.
- Jerk with a Heart of Gold: He does still tries to help others intentionally, even if it doesn't benefit him at times.
- Late to the Punchline: It takes Sam absurdly long to get Superball's "As a medium, I'm more of an extra small" joke, but when he does, he cracks up.
- My Greatest Failure: Sam is unable to save Max.
- Nice Hat: His trademark fedora is so slim, it sits on top of his head. Sometime between episode one and two of the first season he managed to fit an anti-hypnosis device (a coat hanger on top of a colander) in it. It's his buy-in item in Poker Night 2, and Team Fortress 2 fans can win it for their very own, where it's called the "Bloodhound." It's wearable by both Sniper and Spy.
- "Not Wearing Pants" Dream: At the end of "They Stole Max's Brain," we see one of the Samulicra walking towards the duo and Sam makes a crack at the way the clone is dressed hinting that he has dreams about being in public in his underwear.Sam: This is just like that dream I had last night. I wonder if he studied for his finals...
- Only Sane Man: Although he's really not that sane, he comes off as this compared to the rest of the cast.
- Private Detective: His nominal job, although he becomes more of a general-purpose problem-solver/causer as time goes on.
- Psycho Electro: Well, not him. Past Sam, an alternate-timeline Sam created in "Chariots of the Dogs". According to Past Max, he became a monster and was destroyed, much like what happened to Max in "The City That Dares Not Sleep". However, instead of psychic powers, he had monstrous electromagnetic powers.
- Replacement Goldfish: According to Past Max, Past Sam was killed in an incident mirroring Max's death in "The City That Dares Not Sleep", prompting Past Max to time travel in order to team up with Sam.
- Roaring Rampage of Revenge: Sam goes nuclear in "They Stole Max's Brain!" after discovering the titular event, and tears across New York in a barely-coherent hurricane of interrogation until he finds out that his partner's okay. Then he immediately cools down again.
- Sesquipedalian Loquaciousness: Sam is fond of using big words, much to Max's irritation.
- Sophisticated as HellMaximus: Why can't people just all get along, Sameth?
Sameth: Because most people are *bleep*'d, Maximus.
Sammun-Mak: What is a "laser light show?"
Sam: ...Actually, I kind of forget, but I'm pretty sure they're bitchin'.
- Teeny Weenie: A couple of times in the series, Max hints that Sam might be packing light between his legs. Most notably in Reality 2.0, and rather than denying it, he just takes the same jab at Max!Sam: Cool! I have a +2 Sword!
Max: Oh you're just compensating for something!
Sam: You're a fine one to talk!
- The Nicknamer: Lou the Bowling Ball, Steamy the Boiler, Donkey Wrong for Skun-ka'pe, and so forth.
- The Straight Man: This becomes a plot point in one episode where a villain specifically wants a straight man to help out with his plan, and Sam is the perfect kind of easy-to-manipulate character who just does what he's told.
- Sweet Tooth: He's constantly shown with popsicles or ice cream, and is literally unable to resist Fudgie Freeze ice cream bars. This becomes a puzzle in "Beyond the Alley of the Dolls".
- Trigger Happy: Not quite as willing to indulge in gratuitous violence as Max, but just barely.
- Unscrupulous Hero: Sam will do just about anything to solve a case, no matter how much destruction it causes.
Max is a "hyperkinetic rabbity thing" and the second half of the Freelance Police. Unhinged, uninhibited and near psychotic, Max enjoys violence and tends to prefer the aggressive way of solving problems. Still, he has a sharp mind and an observational nature, and it's apparent that his seemingly short attention span is not because of his inability to focus (although that is there), but instead because he grows bored easily and always wants to try new experiences.
Although he seems to have a heartless personality, he seems to genuinely care about his few friends; he strongly believes in protecting Sam and can be pretty possessive over their status as partners and best friends. He dislikes long stories and rambling anecdotes, and occasionally ask Sam or other characters not to use certain words, such as "ensue" or "acumen."
He was born July 10, presumably sometime in the 1970's, and is about the same age as Sam. For unknown reasons, he has a metal plate in his skull, and in the third season, he develops Psychic Powers. He wields a Luger pistol; but since he's naked, other characters frequently ask him where he keeps it, to which he responds "none of your damn business."
- Afraid of Needles: This is only ever mentioned once, but in one of the comics, Max is trying to get a tattoo. When he realizes that the process involves needles, he begins to scream until he actually passes out from fear.
- Ambiguously Gay: Max "doesn't like girls," wishes Sam would stop "looking so damn tasty," constantly attacks Sam (apparently confusing violence with affection,) and confused Sam picking up an engagement ring from the street with a proposal.
- Of course, after you tinker with time in "Chariot of the Dogs", he acts as if he loses loses the "doesn't like girls" part of his personality, especially lusting for Momma Bosco. This actually sticks in the third season.
- In "Poker Night At The Inventory", however, he expresses disgust when asked if he ever slept with Momma Bosco.
- In "They Stole Max's Brain!", Max can talk with General Skun-ka'pe at the planetarium, who claims that according to his scans, Max doesn't like girls despite having expressed a desire to find women. It seems that he really isn't really attracted to the opposite sex, but he feels compelled to act as such due to the aforementioned time tinkering.
- In "Beyond the Alley of the Dolls", he refers to the Sam clones as "sexually provocative" and "dashing." Except for Sam himself, who insists that they're rakishly handsome brutes, everyone else just calls them portly or half-naked. So...
- Again, in "Beyond the Alley of the Dolls", they learn that Bosco had to become a male stripper to pay off his debts to the casino in Vegas. Sam says "Ew," while Max says "Interesting."
- Although he's apparently excited when he hears there's going to be a stripper at Golem Lincoln's bachelor's party... which turns to shock when the stripper turns out to be Jurgen's Monster.
- Ironically, despite the comics featuring the panel where Sam reminds Max that "he's not interested in women", Max actually expresses an interest on several occasionsnote — more so than Sam does, in fact.
- States while his "bliss is seperated" (i.e. his vices are wiped from his personality, leaving him peaceful and sincere) that he would like to have Hugh Bliss's love child.
- Ass Shove: Presumably, where he keeps his gun.
- Attack of the 50-Foot Whatever: Max occasionally sputters out that he wants to do this. And in "The City That Dares Not Sleep", he does...but then he's not really himself.
- Attention Deficit... Ooh, Shiny!: "Quick, let's get out of here before Sam gets distract—ooh, switches!"
- Ax-Crazy: A somewhat benign example.
- Berserk Button: Don't call Max short.
- Even more so, never claim to be Sam's best friend. Demon Peepers never learned, seeing as how Max killed him in about ten seconds when he claimed that.
- Max has numerous other minor buttons based on his ever-shifting mental state, including being compared to his father and having "Walk Like An Egyptian" quoted at him.
- He also developed a severe hatred of Banang after Sam kept the gag going too long, going to great lengths to avoid it being mentioned again. He goes absolutely crazy when it actually does get mentioned.
- Catchphrase: When someone asks where Max keeps anything on his naked person, he usually responds with some variation of, "none of your damn business!"
- Cheshire Cat Grin: His default expression, thanks to his wide, jagged teeth.
- Cool Gun: His Luger.
- Cloud Cuckoo Lander: Max's grip on reality is shaky at best. It's more pronounced in the cartoons, where his inclination to disembowel had to be reined in, but even when he's allowed to be violent, he is (as Sam puts it in the very first episode of the Telltale games) "an unfathomable well of something".
- Cuteness Proximity: When he and Sam meet Baby Jimmy Hoffa in "Moai Better Blues," he's reduced to a pile of mush, squealing things like "He's just adorable!" and "I can't believe how perfect he is!"
- Designated Victim: Not to a ridiculous degree, but since Sam is the player character in the games, it's usually Max who ends up getting captured, killed, or de-brained.
- Ditzy Genius: Max has memorized pi to a thousand decimal places, but can't remember how to open the closet.
- Drives Like Crazy: Both Sam and Max don't pay any attention to the rules of the road, but Max is considerably worse than Sam.
- Everyone Has Standards: In Poker Night at the Inventory, the Heavy's story makes even Max gape; or during Max's conversation with Tycho about what happened during "Chariots of the Dogs.""...are you asking me if I ever shtupped Momma Bosco?!"
- Flanderization: Downplayed, but the Telltale games amp up his implied gayness. The cartoon amps up his wackiness as compensation for not being allowed to showcase his violent streak as much.
- The Gift: His psychic powers in season 3.
- Grand Theft Me: In "They Stole Max's Brain!", Sam puts Sammun-Mak's brain in Max's body because Sal was going to throw it out if he didn't start moving around, fully intending to remove it once they got Max's brain back. Things don't exactly work out; Sammun-Mak completely hijacks Max's body and uses his powers to rewrite reality and make him the god-king of the entire planet. Whoops.
- Guest Fighter: One of the opposing players in Poker Night at the Inventory.
- Hammerspace: One of the possible places the completely naked Max could be storing his gun. This has been left intentionally mysterious, but during a brief body swap in "Night of the Raving Dead", Sam's first comment (in Max's body) was "So that's where you keep your gun!", which implies Max has the gun somewhere on his person, raising another possibility. One of the places you get to visit in The City That Dares Not Sleep, however is stated to be Max's Inventory, which is cluttered with different things he's kept on his person all this time.
- Heroic Sacrifice: In "The City That Dares Not Sleep", the Narrator promises to stay behind and get Max back to normal in five minutes—but they only have four minutes before the last Maimtron is fired. For once, there is no magical Deus ex Machina to help them at the last minute, so when Max's powers finally overwhelm him and he's on the verge of actually exploding, he teleports away to Skun-ka'pe's ship to save the city.
- Heroic Comedic Sociopath: Extra emphasis on the "comedic" and "sociopathic" aspects.
- Hidden Depths: Max is apparently writing a poignant Inuit coming-of-age novel. Except he loses a chapter each time he has to make room for anything else in his brain, such as memorizing a new phone number. Sam discovers an audiobook sample of it, among other planned books, in Max's mind in "The City That Dares Not Sleep".
- The Narrator, his own superego and an integral part of his psyche, loathes him. This pretty heavily points to themes of self-hatred, which coincides with his throwaway comment earlier on that he'd been looking for something to do ever since he found out sudoku "didn't involve ritual suicide" (confusing it for seppuku) and his request to be handed a copy of the magazine "Self-Loathing Weekly".
- Hive Mind: Word of God states that Max's delusions are caused by being part of one, and sharing memories and thoughts with a thousand other Maxes in a thousand other worlds. Later appearances haven't mentioned it, but this could be a good explanation why Sam is completely okay with taking Past Max as a Replacement Goldfish after his current Max's Heroic Sacrifice, since it means they're practically the same Max.
- I'm Taking Her Home with Me!: Despite his sociopathic personality, Max has a fondness for cute things; when he sees something he likes, he will occasionally ask Sam if he can keep it.
- Immune to Mind Control: In the games by Telltale Games, Max can't be hypnotized due to a metal plate in his head.
- Insistent Terminology: Whenever someone tries to describe Max physically, he'll often respond with "I'm a lagomorph." Technically it means he's a member of the order Lagomorpha, which covers all species of rabbits, hares, and pikas.
- Killed Off for Real: One iteration of him, anyway. Fortunately he has a Body Double courtesy of a timeline split in "Chariots of the Dogs".
- Killer Rabbit: Quite literally, though what kind of rabbit is left ambiguous due to the Insistent Terminology above.
- Let's Get Dangerous!: For all his sociopathy, Max's mayhem is usually limited to extremely poor decision-making and offscreen beatings. But in "What's New, Beelzebub?", Demon Peepers makes the horrible mistake of claiming to be Sam's real partner and best friend, and Max literally rips him apart.
- Like You Would Really Do It:We're told from the very beginning that if Max overuses his powers, his head will most likely catch fire and he will explode. That is exactly what happens, and now he's Killed Off for Real.
- Living Weapon: Sometimes Sam will practically grab him and use him in the literal sense. In Sam & Max Hit the Road he's part of Sam's inventory.
- The Magic Was Inside You All Along: For once, played completely straight in the finale of "Beyond the Alley of the Dolls".
- Mood-Swinger: Max can go from calm to completely ballistic in about .05 seconds.
- Morality Chain: Sam actually has a pretty violent temper, and he only really keeps it under control for Max's sake. As soon as he's out of the picture, Sam can totally snap. Max seems to have some awareness of this and will use his influence to either soothe or goad Sam when he loses his temper.
- More Teeth than the Osmond Family: If there's one thing that Max takes seriously, it's his sharp, bear trap-like teeth.
- Never Got to Say Goodbye: Sam and Max never get a chance to say farewell to each other before "The City That Dares Not Sleep"'s finale, because Max never returns to normal after all. All they get is one last wave.
- Nightmare Fuel Station Attendant: "ENJOYING THE RIDE, SAM?"
- Nominal Hero: He rarely intends to save the day; Sam just points him at the bad guys and lets him go wild.
- No Mouth: When his mouth is closed, usually because he's surprised or contemplative, it completely disappears.
- Pet the Dog: No, not Sam; but in "The City That Dares Not Sleep", the player bears witness to the first and last truly unselfish act Max has ever performed during the "Save Sybil" scene.
- Power Glows: Once Dr. Norrington unlocks Max's full psychic potential we see this come into play.
- Power Born of Madness: According to Papierwaite, the only people on this dimensional plane with The Gift are the insane, the simple, or the defective. Max fits all of these categories.
- President Evil: Max gets elected President of the United States in the first season, and it sticks. He moves the Oval Office to his office and enacts various dangerous laws.
- Psycho Sidekick: Sam's lovably homicidal sidekick. Ironically, he's the more powerful of the Freelance Police. He's the president, high priest, and king of three different civilizations, and as of Sam & Max: The Devil's Playhouse, has increasingly powerful psychic powers. There's a point in "Beyond the Alley of the Dolls" where you can read Sam's mind, and find that he's privately worrying to himself that Max won't want a partner anymore, now that he's so strong. Yet he's perfectly happy to follow Sam around and do what he says.
- Psycho Supporter: Of Hugh Bliss. He's also a huge fan of Flint Paper, and once explicitly states that what he respects about him is the fact that he's really insane. He even writes Fan Fiction about him.
- Puppy-Dog Eyes: Part of his Wounded Gazelle Gambit. Doesn't work that well, though, since his beady brown eyes more closely resemble those of a shark than a puppy.
- Replacement Goldfish: After Max's death in "The City that Dare Not Sleep", Sam attempts to clone him from his DNA to replace him and fails. Soon after, though, Sam meets Past Max from "Chariots of the Dogs" and decides that that's good enough for him. It helps that since Max is implied to be part of a multiverse Hive Mind, he's practically the same Present Max in all but cronological memories.
- Riddle for the Ages: Just where does he keep that gun? See Catchphrase above as to Max's usual response, although he did once suggest that he'd tell Sam privately, in a highly controlled situation.
- Ripple Effect-Proof Memory: Max was not affected by Sammun-Mak's changing of history presumably due to having the Gift.
- Stylistic Suck: Max apparently dreams of being a writer, and has hundreds of ideas for novels. But none of them are very...good.
- Temporal Paradox: Despite his death at the end of Season 3, his past self quickly appears from the time traveling elevator to fill his recently deceased future self's place, allowing for more adventures.
- Trigger Happy: While Sam mostly uses his gun to solve puzzles, Max's solution to almost any problem is to shoot it.
- Toilet Humor: His trademark armpit farts.
- Wasn't That Fun?: Expect Max to invoke some variation of this after any death-defying escapade.
- Weirdness MagnetMax: Alien ships love to abduct me. Is it my fault that I look so probe-able?
- Wouldn't Hurt a Child: Max actually seems to really like kids, even though they're obviously terrified of him. Even just having him wave to them reduces them to tears. In "The City That Dares Not Sleep", when Sybil goes into labor, he manages to regain enough control of himself to order everyone the hell out so that she can give birth safely. This is what ultimately proves to The Narrator that he's capable of being selfless and is worth living. This is despite the fact that he was minutes away from exploding and if they'd stayed a little longer, they could have saved him.
- Your Head Asplode: At the end of "The City that Dares Not Sleep", due to an overload of psychic energy and a nuclear bomb stuck in his head.
Sam and Max's most frequent employer, in spite of never having been seen in person. All he has to do is call (or send drum signals, or subspace hails), and any task that's too big, too small or too weird for the regular authorities to handle will soon be taken care of. This when he's not berating the duo for the large amounts of property damage, bloodshed, and general mayhem they're prone to causing. Apparently, he hails from British Columbia.
- The Faceless: So far, a signed picture of his chest has been his only on-screen appearance.
- The Voice: Pretty much, although his voice has never been heard in the cartoon or games. The closest we've come is a word balloon in the comic.
Sharing the office next door to Sam and Max, Flint Paper is more your gritty, hard boiled old school sort of private detective. And when we say old school, we mean Good Old Fisticuffs, lots of gunfire, and pounding on thugs until they squeal. Most of his adventures happen off screen and he's mostly noticed when the sounds of violence leak in from next door but he does occasionally end up helping the Freelance Police and is someone you want on your side in a fight (and not just because the alternative is ending up in a world of pain).
- Hardboiled Detective: He generally functions as a parody of this, preferring to resolve most of his problems with with violence and only being able to think in Private Eye Monologues.
- Hero of Another Story: He is always seen investigating another case, although there is some professional overlap with Sam and Max in season 2 and season 3 where they investigate the same case in a few episodes. As a result of being busy, he is only sometimes helpful even though he really seems to like Sam and Max just fine.Sam: I don't think Flint's taking us seriously, Max.
Max: If I were as cool as him, I wouldn't take us seriously, either.
- Jack Bauer Interrogation Technique: He even gives classes about it!
- Memetic Badass: In-universe example. Sam goes to him for advice on being a private eye, Max writes Fan Fiction about him, and he's well-known for being able to kill anything.
- Metaphorgotten: Speaks and thinks in convoluted noir-tinged metaphors which often end up in...uncomfortably explicit places. And they usually involve hobos, for some reason.
- Nigh Invulnerable: His character description states flat-out that he cannot be killed, though a briefly glimpsed (and quickly averted) Bad Future in "The Penal Zone" does show him taking a hatchet to the back of the head although he actually died from his peanut allergy moments before. In episode 305, during a fight with Skun-ka'pe's clone ape army, he takes a knife to the back of his shoulder. He quickly pulls it out without any indication of bleeding or pain. That could be considered a Shout-Out because Flint was often seen with a knife in his shoulder in the comics. He's probably used to it.
- Private Detective: Of a more traditional sort than Sam & Max, although he engages in plenty of weird cases and gratuitous violence.
- Private Eye Monologue: Apparently, he can only think in these.
- Slasher Smile: Dons a real scary one when leading an arrested Grandpa Stinky to the Pit of Contrition for his supposed heresy against Sammun-Mak.
- Weaksauce Weakness: He is deathly allergic to peanuts. So far, no one has been able to successfully exploit it (although Girl Stinky tried once in The Penal Zone).
- You Didn't Ask: In the final episode of season 2 in the games. He'd figured out that Bosco was, somehow, the vandal his mother was after, but he never mentioned this to her because he thought it was obvious.
The Rubber Pants CommandoesA squadron of gun-toting babies who occasionally appear to rescue Sam and Max from impending peril. They possess surprising combat prowess and an impeccable sense of timing.
- Child Prodigy: They are all infants, save for Sergeant Blip, and capable of taking sown deadly foes with the greatest of ease.
- Deus ex Machina: Pretty much all of their appearances serve as a humorous example of this.
- Everything Is Better With Monkeys: Their chimpanzee leader Sergeant Blip.
The closest thing the Freelance Police have to a recurring arch-nemesis. A fish in a bowl on top of a fake human body, Mack blames the Freelance Police for his current form and vows revenge on the duo.
- Arch-Enemy: He certainly thinks of himself as this to the Freelance Police. He's certainly one of the most recurring, showing up in 3 of the 4 Sam & Max media series (including a very minor cameo in the Telltale series).
- But for Me, It Was Tuesday: He blames Sam and Max for him being a fish in a body suit. Neither Sam, nor Max recall any such event.
- Foil: To Sam and Max. In contrast to their personalities, Mack presents himself as a No-Nonsense Nemesis. His name is even an inversion of "Sam and Max" (try saying "Salmon Mack" a few times).
- Involuntary Shapeshifting: According to him at least. He was a victim of this as a result of the titular duo's actions.
- No-Nonsense Nemesis: At the very least he tries to be one. The Freelance Police don't really take him any more seriously than any of the other weirdoes they deal with.
- Revenge: His hatred of the titular duo is driven by this.
Darla "The Geek" Gugenheek
- Child Prodigy: So much so that the President and the head of the United Nations call on her to stop the hole in the ozone layer and an asteroid crashing into earth.
- Gadgeteer Genius: Is very intelligent and is able to make wonderful toys for Sam and Max, from Humongous Mecha to a speedboat to even a drill to the Center of the Earth.
- Gender Flip: Darla was originally supposed to be a boy. The Geek was changed to girl as the network really wanted a recurring female character in the show.
- Insistent Terminology: She hates being called by her full name.
- Little Miss Snarker: Unlike Sam and Max, she is a lot snarkier and has a drier sense of humor compared to he friends.
- Non-Standard Character Design: She's one of the only human characters in the show whose eyes aren't dots.
- Only Sane Man: She's of more sound mind and less likely to cause mindless chaos than Sam and Max.
- Teen Genius: Only a pre-teen and yet is able to be seen as an equal by Sam and Max, and they love her for her insane genius.
- Tomboy: Given that she was originally gonna be a boy in the concept, it seems she still has a tomboyish personality still as she has no problem with doing dangerous stuff and enjoys the violence as much as Sam and Max.
Ahem. Lorne is an obsessed fan of Sam and Max, alternately eager to come to the "rescue" as much as stage his own drama so he can play Distressed Dude and make Sam and Max need to rescue him. The Freelance Police are a bit split about him: Sam tries to be sympathetic, Max is just plain creeped out.
- Ascended Fanboy: Got a few good points after he kidnapped a villain and nearly killed them.
- Ink-Suit Actor: Bears a strong resemblance to Pat McKenna's best-known character, Harold Green.
- Karma Houdini: In his first appearance, anyway.
- Karma Houdini Warranty: Sam and Max arrest him In his second appearance and then subject him to tremendous electric torture (though Lorne doesn't seem to mind). In the literally titled last episode it is implied Lorne may be in jail for life.
- Loony Fan: Idolizes Sam and Max to the point of being a...
- Psycho Supporter: He sets up a Death Course for Sam and Max to conquer and fakes his kidnapping so he can be "saved" by them. Of course, Sam and Max being who they are, that just finally earns him a few points in their good books.
- Motor Mouth: To the point that Max wants to avoid him as much as possible. He is also very persistent about being their friend.
- Stalker Shrine: was later converted into a fan site that made it so they wouldn't bug them ever again.
Bosco is the owner of Bosco's Inconvenience store and the the Freelance Police's usual go to guy for information or (very overpriced) gadgets. He's cripplingly paranoid of whoever walks in, and in most cases has every right to be.
- Adam Smith Hates Your Guts: Every time Sam and Max try to buy a gadget from him, he comes up with some outrageous price, and his prices get higher each episode. By the end, he lampshades how Sam and Max still come to him.
- Amazing Technicolor Population: He's pale violet for some reason. This gets pointed out, too.
- Anxiety Dreams: Zigzagged. During his stint in hell in the last episode of season 2, he's naked. Then, after Sam & Max free him, he can be seen naked at Golem Lincoln's bachelor party. When Sam mentions he's not in Hell anymore, Bosco states that being naked wasn't actually part of his personal hell and that he just likes being naked. Mind you, he's extremely drunk at the time.
- Ascended Extra: Although his actual appearance was offscreen, Bosco's Inconvenience appears in Sam and Max Hit the Road, 13 years before Telltale made him a major character. Sam & Max...aren't quite as friendly to him in that version.Sam: I didn't realise the lower lip could stretch completely over the head.
- Brick Joke: Multiple times across the seasons.
- In the first season, he wants to build an anti-missile defense system because he believes the US government has a missile trained on him. When Sam & Max make it into the War Room, they learn that's actually the case.
- In the first episode of season 2, he mentions his mother sends him a bomb for Christmas every year. In the last episode of the season, she reveals they're actually only clocks.
- Bunny-Ears Lawyer: He may be a paranoid wacko who sells you "inventions" of dubious quality for exorbitant sums of money, but the gadgets he sells you always do exactly what you need them to.
- Catchphrase: Three of 'em:
- "Hey guys, it's me, Bosco!" when revealing his identity.
- "It'll work, trust me!" regarding his crummy invention of the week.
- "They're onto/after me!" when ranting about the latest conspiracy.
- Conspiracy Theorist: Played for laughs in that even though most of his theories end up being right, he's still portrayed as a complete idiot who is terrible with money, hides behind unconvincing disguises, and doesn't seem to realize that all of his conspiracies could be solved in a day if he'd just give Sam and Max the items already.
- Crazy-Prepared: For all imagined threats under the sun.
- Didn't Think This Through: After Culture Shock, he decides to rework the shop's security system to stop people from being able to plant items in the store...removing the ability for it to stop actual shoplifters in the process.
- Dumbass Has a Point: Once the duo finally protests the escalating prices of his inventions at the 100-trillion-dollar mark in Season 1, Bosco shoots right back that all he does is make up the most ridiculous price he can think of, and each time they keep paying it.
- Gadgeteer Genius: While the ones he sells to others are very rudimentary and border on outright scams (a bottle of vodka labeled "Truth Serum", for instance), he is capable of crafting advanced security systems that can do everything from stop shoplifters to fend off nuclear attacks. Too bad he keeps those for himself.
- Half-Human Hybrid: Invoked In-Universe; he disguises himself as a half-elf when he migrates to the Internet in season 1 of the Telltale Games. Of course, being Bosco, he completely fouls up his disguise by presenting himself as vertically bisected between human and elf.
- I Am Who?: Although he doesn't know it, Sam & Max find out in season 2 that he's actually President John F. Kennedy's bastard son, a result of his mother's brief fling with him and her desire to have a child without a boyfriend.
- Last-Name Basis: Likely enforced by his only referring to himself as his family name of "Bosco". If Momma Bosco is shown his letter from Vegas she reveals that his first name is "Roscoe."
- Naked People Are Funny: He spends the majority of "What's New Beelzebub?" buck naked. At first it seems like this is part of his Ironic Hell, but it's later shown that his hell was being watched all the time. He likes being naked.
- Only One Name: Unlike most other characters, it is questioned as to whether this is a first name or a last name. If an exclamation by his mother is to be believed, though, his first name is Roscoe.
- Paper-Thin Disguise: His preferred way to hide from his enemies.
- Properly Paranoid: His conspiracy theories get more contrived every episode—and they're always correct.
- Put on a Bus: He went to Las Vegas with Buster Blaster in Season 3, and promptly failed to realize that having a card counter that loudly vocalizes every thought is the worst possible idea for increasing his dwindling fortune. He winds up at least $20,000 deep in debt to what's implied to be the mob and is, thankfully off-screen, forced to work as a male stripper to pay it off.
- Rags to Riches: Because of all the money he makes out of Sam & Max in the first season, he retires his shop in the 2nd.
- Riches to Rags: However, as of the 3rd season he's burned through his fortune enough that he goes to Vegas with Bluster Blaster as his card counter to try and revitalize it. This fails because he chose Bluster Blaster as his card counter and he winds up deep in debt and working as a male stripper to pay it off.
- Sanity Slippage: His mental state is constantly degrading during Season 2, leading to his being abducted by T.H.E.M. This slippage reaches its climax when he and Momma Bosco's ghost meet in the present and he realizes that every bit of his paranoia is because his mother was looking for his temporally displaced self. After that moment of lucidity, he snaps again and develops a twitch in his eye.
- Shoplift and Die: More like "Shoplift and Get Bonked By a Boxing Glove", courtesy of BTADS (Bosco Tech Anti-Delivery System). He even integrated his anti-missile satellite defense system into BTADS.
- Temporal Paradox: In episode 204, when he ends up aboard the time-traveling spaceship of T.H.E.M, he inadvertently travels back to his shop when his mother owned it in 1962, where his panic at seeing her causes him to damage some things. She declared a vendetta against this "mysterious vandal" that resulted in her inadvertently harassing him throughout his life. Also overlaps with Grandfather Paradox, as he inadvertently contaminated his mother's Uterine Replicator with cow's milk and caused himself to be turned into a half-human, half-cow. A condition that Sam & Max temporarily exaggerate.
- Twitchy Eye: When he finally learns that the people harassing him over his life have mostly been detectives trying to find the man who vandalized his mom's store before he was born — which was Bosco himself, due to Time Travel — he develops a very twitchy eye, then promptly scares his mother by ordering her to get out of his proverbial hair.
- All Girls Want Bad Boys: When Max bluntly insults her and tells her that he's not interested in her, she immediately becomes infatuated with him, even declaring she'll give up her original plans to become a single mom. Ironically, when Sam then adjusts Max so that he does express an interest in girls, she promptly does another 180 and goes back to hating men again.
- Back from the Dead: By possessing a less-than-perfect clone of her.
- Bald Women: After being resurrected through a clone. To be fair, this isn't so surprising when you consider that 1% of the DNA used happened to be from Bosco himself to patch up her DNA, which just so happened to reflect his lack of hair and part of his attitude.
- Does Not Like Men: Is constantly putting men down and denouncing them at the slightest excuse for perceived sexism. That said, this only applies to her young self in the 1960s; the older Momma Bosco from season 3 has seemingly grown out of this.
- Funny Afro: Only loses it when she is originally brought back from the dead. Later regrows it though.
- Gadgeteer Genius: Makes a child-making device, hundreds of cloning machines, and a portal to another dimension.
- Insane Troll Logic: Much like her son, her rationale behind her decisions... don't make a lot of sense. A saner alternate version of Bosco mentions that his mother is "extremely contrary". Seems to have gotten saner by the events of season 3.
- Interspecies Romance: Played for laughs, but she is initially attracted to a time-traveling Max.
- Nice Job Breaking It, Hero!: Her obsession with finding out who the person who wrecked her store is directly the cause of Bosco's rampaging paranoia as she hired detective after detective to find someone who perfectly fit his description not knowing that the person she'd been hunting for was a time-displaced Bosco himself. She shows regret and shame when she learns she's the reason Bosco is the way he is.
- Straw Feminist: Played for laughs. Momma Bosco is not only a Sassy Black Woman, but is also very annoyed when others (in her eyes) fail consider that she is an 'independent' woman and doesn't need a man for anything, even to have a child. However, she ends up falling for Max of all people.
- Techno Babble: A never-ending fountain of this in Season 3. Eventually, she confesses that she's just making it all up as she goes.
- They Call Me Mister Tibbs: She insists on the salutation Dr. after earning her PhD.
- Took a Level in Kindness: Being dead must have mellowed her, to the point of being one of the most helpful characters in Season 3.
- Uterine Replicator: Builds a device that can take DNA from two people and mix them together to create a fully-developed child without the need for her to ever be pregnant or engage in sex. In the 1960s.
- Why Couldn't You Be Different?: Implied; in her first appearance in episode 204, she makes it very clear that she's expecting her artificially produced child to be a daughter, and that she really isn't a fan of the male gender. With Bosco making it clear how poorly he and his mother get on, it's obvious that she never did forgive him for being her son instead of the daughter she wanted. Despite this, she does still love her son greatly.
- Balloon Belly: After spending most of Season 3 out of action due to being still on her honeymoon, Sybil makes her triumphant return in the final episode to help Sam... Thing is she is also HEAVILY pregnant. She is decidedly insecure about her protruding gut, which becomes a problem when Sam offends her by accident.
- Bridezilla: Implied; in the season 2 finale, her preparations for her upcoming wedding to Lincoln have Jurgen's Monster, who she is using as her sounding board, begging for death. And Sam actually has to shoot him (temporarily) dead in order to complete a puzzle. Of course, it could just be the fact that the Monster is being made to help plan his unrequited love's wedding to another.
- Longest Pregnancy Ever: Justified, as she's carrying some sort of human-golem hybrid in her. That sounds like it would take longer to develop. That doesn't change the fact that she's in her fifth trimester.
- New Job as the Plot Demands: Provides the page image. She rarely holds the same job twice, and they get more outlandish each episode.
- Nice Girl: If only by comparison. She's one of the few characters that shows Sam and Max even common courtesy instead of brushing them off; for example, she greets them by name instead of "Oh, it's you two".
- Only Sane Man: For a little while, she appears to be the only rational, although a little scatterbrained, character in the series. Then she falls in love with and marries the Lincoln Memorial.
- Pregnant Badass: In the Season 3 finale.
- Punny Name: It appears to be a play on the term "civil pandemic".
- Put on a Bus: She's still on her honeymoon in Season 3. But she returned in time for the finale.
- What Does She See in Him?: Several other characters wonder just why it is that Sybil is attracted to the Lincoln Memorial during Season 2. Most notably, during "Moai Better Blues", if you talk to Girl Stinky at the start of the chapter and ask her how to "help Sybil", she suggests that Sybil should dump Lincoln. Later in that chapter, their relationship hits a rocky spot when she finally clues in that he's insisted on their particular picnic spot so that he can ogle the Moai statue nearby... which he compounds by suggesting she get plastic surgery to look more like her!
Philo Pennyworth / Mr. Featherly
- Classically Trained Extra: Zigzagged. He's obviously doing roles far beneath his talent but doesn't seem all that bothered about it, explaining to Sam & Max that a true actor should give their all for whatever role they've been cast... even something as absurd as this. Once Midtown Cowboys becomes a smash hit in Germany, he's actually quite happy with it, and happily abandons plans of acting in theater again because his Mr. Featherly role is far more profitable.
- Fake American: He talks with an English accent, but drops it for his Midtown Cowboys character.
- I Am Not Spock/I Am Not Leonard Nimoy: Undergoes both tropes. In the first season, he gets annoyed when people mistake him for his sitcom character. In the second season, after Midtown Cowboys turns into a surprise hit in Europe, he legally changes it to Mr. Featherly to make it easier to cash in on that foreign popularity and is now irritated whenever someone calls him Philo Pennyworth.
- Live Item: In Chariot of the Dogs.
- Money, Dear Boy: The reason he's fine with starring in such an awful sitcom, especially once it finds a huge audience overseas. He's not selling out his principles for money... He's selling them out for a SHITLOAD of money!
- Everyone Calls Him "Barkeep": No name is ever mentioned. She's just "The Director."
- Offscreen Teleportation: She can appear in every room just before you enter, but refuses to tell how that's possible. Industry secret.
- Prima Donna Director: Subverted, surprisingly. The Director is cranky and short-tempered, but mostly because of the extreme stress of running an entire TV studio with only a skeleton crew. She's actually pretty patient with Sam and Max, even when they're actively trying to annoy her, and will do as many takes as are needed without blowing her top.
- Product Placement: She's a huge fan of the revenue they bring in, and works them into the Midtown Cowboys script no matter how inappropriate or bizarre they might be.
- Drill Sergeant Nasty: A somewhat ineffectual one, thanks to his stature.
- Chuck Cunningham Syndrome: Unlike most of the other characters that disappeared at the beginning of Season 3, there's no reason given on why he wasn't included, implied or otherwise.
- The Informant: Well, he is a ''bug''...
- Literal Surveillance Bug: He's a talking cockroach that listens to and flawlessly repeats whatever he hears. That's as literal as it gets.
- Live Item: Sam keeps him inside his coat, like everything else.
- Shell-Shocked Veteran: When he isn't bossing Sam around, he's looking back on his traumatic war experiences. He even has "Post Insecticide Stress Disorder", causing him to rant about events tied to specific smells. When he smells bleach, he flashes back to a battle over Hamburger Hill (a garbage pile behind the Burger Buddies restaurant on West 5th Avenue, not the one in Vietnam).
- Verbal Tic: Whenever he says something, he usually says the last word twice. Twice!
- Becoming the Mask: After disguising himself as the don of the Toy Mafia for a sting operation, he settles into the role so much he actually becomes don of the Toy Mafia.
- Butt-Monkey: Almost nothing goes his way, especially when Sam and Max get involved. For example, in "The Penal Zone", he trades an (unknown to him but known to Sam and Max) winning lottery ticket in exchange for one of General Skun-ka'pe's "vacation tickets"...which are actually keycards to the general's moleman processing machine. Not only did he lose out on millions of dollars, he almost got killed.
- Don't Fear the Reaper: Had a brief stint as Death.
- Early-Bird Cameo: He can be seen on a poster in Brady Culture's Home for Former Child Stars in "Culture Shock" before he properly appears two episodes later.
- Fantastic Racism: He has a deep and intense hatred of zombies, due to their clumsiness and habit of breaking knick-knacks.
- The Mole: Quite literally in "The Mole, the Mob, and the Meatball".
- New Jobs As The Plot Demands: Not nearly as often as Sybil, but he's been a police informant, don of the crime syndicate he was infiltrating, docent of the Church of Prismatology, potential suitor of Sybil, the Grim Reaper, and wannabe spirit medium.
- "Awesome McCool" Name: Although "Superball" is initially implied to be a code name, we later learn that there's a Mrs. Superball and a Superball Junior. Becomes even more awesome in the German translation, where his name is "Agent Superblocko." He states it's a joking reference to his designated primary role of governmental bouncer in his debut and the him from the 60s parrots his claim in "Chariots of the Dogs".
- Cool Shades: "These sunglasses aren't cheap."
- Creepy Monotone: The dude's not fazed by anything, though he claims otherwise.
- Hidden Depths: Apparently he has a really good singing voice, as shown in The War Song.
- He also took twelve years of professional dance lessons.
- Manly Tears: Subverted. After the failed attempt to clone Max following his death, he declares that he "can't do this," and bursts out sobbing.
- Mysterious Past: If you use the Nutrition Specs on him, Sam says that he's comprised of "20% mysterious, and 80% sheer awesome.""Hmm, that's down 10% from last season."
- Not So Stoic: Max's death is too much, even for him, and causes him to run away while crying uncontrollably.
- Older Than They Look: Looked exactly the same age way back in The '60s when he started the job. When asked, he Hand Waves it as "clean living". Superball gives the Hand Wave in response to Sam's assertion that he looks as young as he does due to time travel.
- Psychic Block Defense: "I am afraid that the contents of my mind are classified, sirs."
- Punny Name: Superball is a "bouncer," get it?
- Ripple Effect-Proof Memory: Along with Dr. Norrington, the Molemen, Max, and the organization he works for, he did not have his memory affected by the Sammun-Mak incident.
- Single Tear: He sheds one in a vision of the future, but if it ended up happening, we missed it along with whatever truly beautiful or tragic thing provoked it. Given the context of the season's ending though, it's likely it was his reaction to seeing Max's Heroic Sacrifice or the start of his Inelegant Blubbering.
- That Makes Me Feel Angry: Because he rarely actually emotes.Superball: (Complete monotone) That makes me extremely alarmed.Max: Get a hold of yourself, man. We can't think with all your hysterics.
The Giant Stone Head of Abe LincolnIt Makes Sense in Context. After losing to Max in the election, he went on a rampage through the US and was blown up by a nuclear warhead, leaving only his disembodied head. He later marries Sybil Pandemik, whom he met when Sam arranged a date between the two of them to scandalize him and lower his ratings in the aforementioned election.
- Golem/Humongous Mecha: Seems to be a mix of the two; he is made of marble and very towering in height, but it sounds like his body has robotic parts to help him move around.
- HeelFace Turn: Started as an enemy of Sam and Max, later reforms when they help him get with Sybil.
- Kavorka Man: He's not exactly a handsome man, given he's a giant sculpture of Abe Lincoln's severed head, but the attractive Sybil Pandemik is dating him throughout Season 2... despite some rough spots here and there, they ultimately get married, to everyone's disbelief.
- Losing Your Head: Inverted; he was reduced to a head when he got blown up by a missile. Got his body back in Season 3.
- Put on a Bus: He's still on his honeymoon with Sybil in Season 3, though he comes back in the last episode to lead the Maimtrons' charge against the rampaging monster.
The Computer Obsolescence Prevention Society (C.O.P.S.)
- Berserk Button: WE HATE BAGPIPES!. They also deeply resent the Torture-Me-Elmer toy, and their first challenge to Sam and Max is to run over and shoot as many of the masochistic dolls as possible.
- The Bus Came Back: Buster Blaster came back from his trip to Las Vegas, though without Bosco, in "Beyond the Alley of the Dolls". He's gone again by "The City That Dares Not Sleep", having run off with Carol.
- For Inconvenience, Press "1": Played with at times with Bob the telephone.
- Fun with Acronyms: This leads to a little confusion when Sybil first mentions them.
- Heroic Comedic Sociopath: Bluster Blaster.
- I Want My Beloved to Be Happy: Carol leaves the C.O.P.S to run away with Bluster Blaster, but Curt claims that he's fine with this as long as she's happy.
- Large Ham: Especially Bluster Blaster."I AM BECOME DEATH!!"
- Luke, You Are My Father: It turns out Sam created Bluster Blaster.
- Machine Monotone: Curt 286.
- No Indoor Voice: Bluster Blaster, for the most part. He temporarily gets a quiet Simpleton Voice due to an accident just before "Night of the Raving Dead", but he's back to his usual noisy self by season 3.
- Noodle Incident: Towards the end of season three, reading Bluster Blaster's future shows him, apparently, enthusiastically drifting through space. We're given no clue as to why.
- Additionally, Bluster Blaster's words imply he had a falling out with the rest of the C.O.P.S and it's never elaborated over what, though it's very likely it has something to do with his lightning-induced injury from testing the antenna in Night of the Raving Dead and the fact that the other C.O.P.S tried to profit off the excess of his prescription medicine.
- Put on a Bus: In Season 3, Bluster Blaster is on a road trip with Bosco to Las Vegas.
- Quip to Black: Curt gets his by the boatload in 305.
- The Speechless: Supposedly Carol, but it's equally possible she's just a regular, non-sentient machine and the C.O.P.S. are just delusional.
- Token Girl: Carol—or so the C.O.P.S. claim. "She" never speaks or displays any signs of sentience, so there might just be a weird case of Cargo Ship.
- Tropaholics Anonymous: They're a quartet of old computers that spend most of their time trying to get past how old they are.
- The Unintelligible: Chippy only communicates in electronic boops and bleeps, although there may be more to it than that.Max: That one'snote my favorite. It sounds like he's always cursing.Curt: That is because he is.
- We Want Our Jerk Back: Bluster Blaster, after his "accident" in Night of the Raving Dead.
- What the Hell, Hero?: They're horrified when Noir Sam threatens Carol at gunpoint in "They Stole Max's Brain". They've gotten over it by their next scene, though.Bob: Audiences across the country agree: you're a monster, Sam!
Curt: What have you become?
- Butt-Monkey: Double-Subverted; even Max is incapable of making fun of him, given how nice and simple he is; but every puzzle solution which involves Sal will somehow inflict physical damage on him.
- Gentle Giant: Despite being a giant cockroach, he's actually a skilled chef and a very nice guy Makes it a Tear Jerker when he dies from radiation poisoning.
- Heroic Sacrifice: Undergoes death by radiation poisoning to save the city.
- Nice Guy: As mentioned above, Sal really is a good guy to know. Even Max doesn't have the heart to make fun of him via Psychic Ventriloquism.
- Starcrossed Lovers: Has been carrying on an affair with Girl Stinky, which is genuine on his side.
- Brilliant, but Lazy: She's lazy as hell, but she manages to come up with a decent plan to get rid of Grandpa Stinky in "The City That Dares Not Sleep". She would've gotten away with it too, if it weren't for Sam. Not to mention the various secret tunnels she's installed in the diner, which, again, weren't noticed until Sam got to them.
- She's also the only non-supernatural being who will notice if Max tries to use mind-reading on her (besides Sam, of course).
- Consummate Liar: Getting a word of truth out of her is a never-ending war. Most of the cast gives up by the start of season 3.
- Hesitation Equals Dishonesty: Subverted, actually.
- Implausible Hair Color: The only human we've seen with an unusual hair color (seafoam green). A hint at her (possible) supernatural origin.
- The Munchausen: In Season 2, she tells all sorts of outlandish lies about her adventures with various celebrities.
- Obviously Evil: Everyone knows she's planning to kill Stinky to get his diner, which she denies (poorly), but nobody cares.
- Our Homunculi Are Different: Created from a cake. An evil cake, made from an entree, dessert, and side...and an appetizer... Or maybe not, if Flint's projector-and-fog-machine theory is actually correct.
- Our Mermaids Are Different: As something of The Un-Twist in "The City that Dares Not Sleep". She wears a tiara, she has a seashell necklace, she has a sea star on the back of her ponytail, she has an Implausible Hair Color, she has a fish on her apron to make up for the signature tails associated with mermaids, and she can go by Stinky and be followed around by flies because those are fish things. Mind you, the man suggesting this is Flint Paper, who is... not altogether there, and we see her change back and forth between human and cake forms in the second season's final episode.
- Phoneaholic Teenager: She spends almost all of her time in Season 3 texting/calling Sal.
- Psychic Static: Not only is she one of only two non-psychic characters to notice Max can read her mind, but she's the only one that can counteract it—by thinking about shoe shopping. Max is horrified.
- Red Herring: A very fishy lady, but she's rarely directly responsible for whatever's going on at the moment. Her story about Grandpa Stinky's round-the-world cruise/Himalayan mountaineering adventure seems like an obvious lie, but is not only completely true, but his death is actually Sam and Max's fault due to their time-traveling antics.
- The Slacker: Never seems to actually run her diner, and spends almost all of Season 3 texting. Most puzzles involving Stinky involve trying to work around her lies, her laziness, or both.
- Starcrossed Lovers: It looks like that between her and Sal, but she dumps him when Skun-Ka'pe provides a better opportunity to kill Grandpa Stinky. That, and Sal had just been eaten by Max.
Grandpa StinkySocial Darwinist, and overall grouch.
- Back from the Dead: As of "What's New, Beelzebub?".
- Evilutionary Biologist: His ultimate plan is to improve the human race by culling those too weak to eat his vile cooking.
- Father Neptune: Looks and acts like a man who has been out to sea at times, and even acts as a sort of tough guy.
- "Freaky Friday" Flip: With one of Skun-ka'pe's mooks in "The City that Dares Not Sleep". And after all's said and done, he doesn't get his body back.
- Giftedly Bad: The man was able to make a thinking, human(ish) being by making a cake out of tar, fish fingers, coffee ice cream and a rib. Even he wasn't expecting that variation on the Cake of the Damned to turn into Girl Stinky.
- Greed: Most of his plans in Season 3 involve making a fortune with his evil recipes.
- The Insomniac: As of the end of Season 3, he hasn't slept in 1096 days (3 years).
- Killed Off for Real: Only halfway; his body is destroyed in the nuclear explosion that also killed General Skun-ka'pe, Girl Stinky, and Sammun-Mak. On the other hand, his brain was transferred into one of Skun-ka'pe's gorilla henchmen, so he may return.
- Lethal Chef: He is being one on purpose, in an attempt to weed out "inferior" people that can't handle his awful food, thus creating a master race.
- Let's Get Dangerous!: "Looks like it's time to boil the haggis!"
- No Celebrities Were Harmed: Looks and sounds quite a bit like Sean Connery.
- Social Darwinist: Wants to create a master race who can survive his toxic recipes.
- Tattooed Crook: The tattoo on his forearm spells "Satang" in Nordic runes.
- Catchphrase: "Beat it."
- The Informant: Well, he is a rat.
- Hidden Depths: He is a petty criminal, but he's doing it to support his son Timmy. When he isn't involved in some scheme, he lobbies for affordable healthcare for the aged and underprivileged (as shown in "Abe Lincoln Must Die!")
- Morality Pet: Jimmy is incredibly rude to everyone—except his son Timmy and his wife Mary. He's a total softie around them.
- Put on a Bus: It's implied in season 3 that he's living it up on the money Max paid him for spreading the bubonic plague.
- Red Boxing Gloves: Eventually confiscated by Max. Implied to be loaded, which is why he's so dangerous when using it.
- You Dirty Rat!: While has a few soft spots, Jimmy is a thoroughly unpleasant petty crook.
- Back from the Dead: Is killed and revived by Sam and Max in "What's New, Beelzebub?".
- Hollywood Tourette's: He's afflicted with "Terminal Tourette's Syndrome", which causes him to "curse" uncontrollably and will kill him if he sets it off too much. It's revealed at the end of season 2 to be a more realistic case than originally assumed as he's not really swearing at all. Hell's censorship department was simply being too overzealous with him and the feedback was causing him pain. Once he's uncensored he notes that his health has improved.
- Littlest Cancer Patient: Played for Laughs. Timmy somehow manages to make Hollywood Tourette's seem like a serious affliction.
- Sir Swears-a-Lot: Subverted; once uncensored, his vocabulary is PG-rated at worst.
- Symbol Swearing: Humorously, he only knows how to write using this as he hasn't gotten to proper letters in his home-schooling yet.
Satanuntil the Soda Poppers took it over, at least.
- Affably Evil: He's technically evil, but he's polite, soft-spoken, well-mannered, an equal-opportunist employer and all around perhaps the friendliest person you meet in the games after Pedro and Sybil.
- Big Red Devil: Has the Classic Satan look; huge horns, red skin, and goat-like legs.
- Deal with the Devil: Actually manages to pull one of these on Sam, but it doesn't last long.
- Do Wrong, Right: After Sam & Max accidentally get him fired from his position in Hell, he explains he's actually very proud of them, because even if it caused him some inconvenience, they were engaging in the kind of behavior that he pioneered.
- The Devil Is a Loser: In episode 205, he is actually just a middle-level manager in Hell under the Soda Poppers. When he gets fired, he ends up homeless and cleaning windshields for spare change.
- Not-So-Harmless Villain: Played for laughs; in the epilogue of episode 205, he mentions to Sam & Max that they are "going to be seeing quite a lot of each other", making it obvious that they are still damned to go to Hell when they die because... well, they're Sam & Max, you need a list? Neither of them catches on to the insinuation, though.
- Punch-Clock Villain: You can hardly call him an antagonist. In fact, you actually have to help him at one point.
- Wimpification: Invoked In-Universe; episode 205 has him explain that his powers have dwindled as a result of people treating him with less fear, courtesy of his appearance in things like mascots or advertising logos.
The Narrator / Max's Super-ego
- Affably Evil: He's pretty deadpan and calm when he explains his evil plan. He even apologizes for his crack about Sam's weight.
- And I Must Scream: His backstory. Max doesn't so much personify pure id as completely ignore his superego, which leads to the Narrator feeling neglected and frustrated. Eventually, he grows so tired of being ignored and having no way to express himself that he decides to make it all end - in a fantastic psychic explosion (that will destroy the whole eastern United States), created by pushing Max's mind as far as it can go.
- Big Bad: Of the whole Season 3, it turns out.
- The Conscience: Literally. Subverted in that he's initially out to kill Max for always ignoring him.
- Deliberately Monochrome: As part of Season 3's Twilight Zone-esque theme. If you really think about it though, it also works a bit in its own right. He's Max's super-ego, one of the most firmly practical and logic-driven parts of the brain... i.e., "seeing the world in black and white."
- It apparently applies to his room in general: When Sam walks in on him in The City That Dares Not Sleep, he also turns black and white except for his tie, which turns red. He only goes back to normal when leaving the room.
- Despair Event Horizon: Goes through this before the events of the season due to never being recognized or listened to, driving him to enact his plan to kill Max, and by extension himself, along with most of the Northeastern US.
- Disproportionate Retribution: He's tired of getting ignored, so he's going to kill Max by pushing his mind to its limits and making him actually explode. Then again, considering he's Max's conscience, and Max is, well... See And I Must Scream and Despair Event Horizon.
- Driven to Suicide: His master plan is to finally free himself of the burden of being Max's unappreciated, unused superego by having Max overwork his brain until he can go out in a fantastic psychic explosion that will destroy the eastern United States.
- He changes his mind when he realizes that Max is capable of selflessness, but still gets his previous wish in the end.
- Foreshadowing: A delightfully meta case at that. His voice actor, Andrew Chaikin, was Max's voice in the first episode of the Telltale series before being replaced the very next episode.
- Fourth-Wall Observer: While some other characters have this trait to a degree, he is the one who speaks the most directly to the audience. He even keeps addressing them after the reveal.
- Ghost in the Machine: He's the sentient manifestation of Max's superego (conscience), who lives inside his brain. And no, his existence has not been an easy one...
- HeelFace Turn: May be a subversion or a HeelFace Door-Slam depending on whether-or-not Max actually exploded at the end.
- Hidden Depths: Not for the Super Ego himself, but for Max. Considering his own Super Ego hates him, this seems to imply Max has self-loathing problems. This makes a few previous jokes in the series a bit more tragic.
- Interactive Narrator: Subverted. He actually does exist within Sam & Max's universe, since he's really Max's super-ego and lives inside his brain, but continues to narrate somewhat and address the audience beyond the fourth wall even after this is revealed.
- Large Ham: Anybody can just narrate a story. This guy throws so much charismatic flair into it that he'd put Rod Serling and Alfred Hitchcock to shame.
- Mr. Exposition: He spends most of his time narrating the beginnings/endings of The Devil's Playhouse's episodes. There's far more to him than that though...
- No Respect Guy: He's spent God knows how many years trying to guide Max into controlling his most primal urges, appreciate the finer things in life, and act selfless as well as socially acceptable. Of course, it's all in vain, and he is never recognized for his efforts.
- Sarcasm Mode: If told he's lying about his role in the events of the season, he proceeds to spin an absolutely hilarious yarn about being an angel or some such. He then makes it even funnier by saying that's ridiculous and that his being the manifestation of the super-ego of a talking rabbit who has psychic powers is a simpler and more believable explanation. It doubles as a huge Take That! to the fans who were insistent that he was some mighty benevolent force acting to help Sam and Max.
- Something About a Rose: The only bit of color on his person is a single red rose.
- Villainous BSoD: Breaks down into this when Max decides that everyone should save Sybil, rather than simply going on selfish impulses, realizing that Max does still have hope to be better.
- Walking Spoiler: He plays an integral role in the final episode of The Devil's Playhouse.
- Woobie, Destroyer of Worlds: While not always a particularly popular opinion, definitely a possible and existing one, due to his And I Must Scream backstory. note
Sameth and Maximus
- Fingerless Gloves: Maximus wears the "Hobo Gloves" version.
- Identical Great Grandfathers: The only differences between them and their descendants are that Sameth has a mustache and Maximus wears clothes.
- Nice Hat: Sameth's bowler hat. Maximus also would've had a Newsie Cap, but it was removed since it kept clipping through his ears. You can still see it on the concept art that appears on the transition cards for the episode though.
- The Slacker: Unlike their great-grandsons, who have a job of sorts, they don't seem to do anything more than sneak into theaters and steal ketchup bags from restaurants. The two of them are implied to either be vagabonds or con-men.
The Mole CultistsThe remains of the molemen. The molemen were the ones who deposed Lord Sammun-Mak years ago and guarded the Devil's Toybox. Millennia later, the last of the molemen (Nefertiti, her father, her mother, and her grandfather) emigrated to New York when the box was stolen by Sameth and Maximus, where they once again gained the Devil's Toybox. A century later, the last cultists guard the toy box when Sam and Max find it.
- Generation Xerox: All the molemen look the same except for whatever they are wearing.
- Identical Grandson: Either Harry is over a hundred years old, or one of his ancestors has the exact same voice as him.
- La Résistance: To Lord Sammun-Mak's reign.
- Never Mess with Granny: Nefertiti lives to the modern day and helps take down Sammun-Mak.
- Ripple Effect-Proof Memory: Were unaffected by Sammun-Mak's changing of history due to their Molemen heritage.
Doctor Norrington/Yog-Soggoth, Elder Fiend of the Dark Dimension
- Anti-Villain: He has mellowed into this by the time we meet him, and seeks to preserve the real world rather than destroy it.
- Big Bad: Subverted. Though his actions in the backstory drive the plot of the season and the story seems to set him up as one, he never serves as an antagonist and actually helps Sam and Max.
- Celebrity Impersonator: He sounds remarkably like Tony Jay. Perhaps justified, since this is the type of role he often takes. Considering what he is, it could be a Shout-Out to Jay's role in Legacy of Kain.
- Deadpan Snarker: Occasionally. Mostly towards Papierwaite and his near constant whining from Episode 4 on."Walk it off, Princess."
- Did We Just Have Tea with Cthulhu?: He's surprisingly suave and personable for an Elder God.
- Eldritch Abomination: A very washed-up one though.
- Evil Is Not a Toy: Downplayed. He was the creator of the Toys of Power and stresses several times that they need to be destroyed in order to preserve the boundaries between the real world and the Dark Dimension. He doesn't deny they're toys, but they're toys meant for an Elder God. Not for mortals to screw with.
- I Was Quite a Looker: He claims this if you examine a certain object in Papierwaite's office while he's present.
- Large Ham: By way of Purple Prose.
- Retired Badass: He once ruled the entire universe and savored the taste of human misery along with the other Elder Gods, but has since claimed age has mellowed him.
- Sesquipedalian Loquaciousness: To Max's chagrin.
- Stop Worshipping Me: He never wanted anyone to summon him. He was perfectly content being left alone in the Dark Dimension with the other Elder Gods, and now all he wants to do is to go back home. Papierwaite's awe-struck reverence seems to get on his nerves, too.Max: You look like something my non-existent cat coughed up!
Papierwaite: Curb your tongue, rabbit—
Yog-Soggoth: No, no, Papierwaite, the naked one is right! This debased form is but a pathetic shadow of my former glory!
- You Cannot Grasp the True Form: Or so he thinks. He states most humans go mad upon seeing him, but none of the characters who have been known to have seen him seem affected. He is significantly depowered, however, so that might be a factor.
- Attention Whore: His plan was to hypnotize the world into worshiping him. Sam uses this to his advantage to defeat Brady.
- Big Bad Wannabe: At best, he managed to hypnotize three washed-up child stars to do graffiti, stuff a therapist into a closet, and fill a convenience store with free tapes. He didn't even make his "ocular exercises" on his own; Brady stole prototype hypnosis goggles from Hugh Bliss' gift shop on the moon.
- Evil Laugh: Needs practice at first. He gets better at it.
- Funny Afro: The Freelance Police keep it as a memento afterward.Max: He howled like a sick wallaby when I shaved it off him! Good times.
- Starter Villain: The first antagonist in the Freelance Police games, and the only one not directly working for Hugh Bliss or his organization in the Save the World arc.
- Blah Blah Blah: Her ranting quickly devolves into this.
- Brainwashed and Crazy: She's actually being hypnotized by one of the Toy Mafia's hypnotic teddy bears.
- No Celebrities Were Harmed: Think a naggy, scandal-hungry, and white Oprah Winfrey. She even gives her audience members gifts, although she's reduced to giving them non-dairy creamer after days of holding them hostage.
The Toy Mafia
- Blatant Lies: Ted E. Bear's Mafia-Free Playland and Casino! Bring the whole family!
- Creepy Monotone: Cuddly Bear, the card dealer. "Wanna play cards?"
- The Family for the Whole Family: They're involved in all sorts of illegal activities, but at least they aren't gunning down people at toll booths or crushing people's heads in vices.
- Played With, as while two of their quests they give to Sam and Max are relatively benign (namely stealing something back that was stolen by another criminal, and forcing a store to stock Ted E. Bear merchandise against their will), their third task is to murder Sybil to prevent her from testifying in court as a witness against the Mafia, and to ensure the kill is gruesome to warn other would-be rats - while Sam and Max thankfully find a way to fake Sybil's death through a textbook Staged Shooting, as far as the Toy Mafia was concerned, they saw Sam using his big gun to blast a hole in Sybil's chest. And when Sam and Max blow their cover to the literal Mole in Charge, the Toy Mafia chases after the duo's De Soto in their own car, firing their own pistols with full intent to kill. Overall, the game proves that the Toy Mafia are willing to kill rats and coppers, it's just never shown to succeed on-screen to keep the game's age rating down.
- Malevolent Masked Men: Every member wears a giant multi-colored teddy bear head.
- Man Behind the Man: The Toy Mafia is sandwiched firmly between both sides of this trope, at they're revealed to have been the ones to have brainwashed Myra Stump through one of their hypnotic teddy bears... And in The Stinger of 103 Chuckles reveals he's a Man In Black (Agent Chuckles), who was using the Toy Mafia to distribute the hypnotic teddy bears under orders from the US government. Only for episode 104 to reveal Agent Chuckles was really taking orders from the Internet (as in, the Anthropomorphic Personification of the Internet, as a AI trying to trap everybody in the "Reality 2.0 game"), and then episode 105 to reveal the Internet itself was corrupted by "Roy G. Biv", a.k.a. Hugh Bliss! It's... complicated, to say the least.
- Paper-Thin Disguise: The enterprise as a whole to the point of parody.
- Zig-Zagged, in that the masks themselves successfully conceal the voices and identities of each member (to the point that it's dramatic when they take them off to reveal their true identities. Whether it's the literal Mole in Charge, or a Man In Black manipulating the Toy Mafia as part of a Government Conspiracy)... But between the multi-colored gangster suits and fedoras, and talking exclusively in mafia-movie Wiseguy cliches, and it sinks any chance they have at convincing anybody they're not criminals.
- Suck E. Cheese's: Their "Mafia-free" Playland and Casino is, well, The Casino version of these, as all the "staff" wear "costumes" with bear heads, and the games and decoration have utterly cheesy theming, from a a slot machine shaped like a literal "One-Armed Bandit", to a "Whack-the-Rat" game where the player shoots rats that are "singing", and avoids the ones who "keep their mouths shut".
- Villain Song: "Just You and Me (And Ted E. Bear)"
- Welcome to Corneria: The card dealer, again.
- Abhorrent Admirer: To The Director.
- Affably Evil: He's friendly
- Big Bad: Of Season 1.
- Camp Gay: Well, gay as in happy, at the very least. But between the high-pitched voice and the enthusiasm for unicorns (he's the only one who seems willing to rub Sam's unicorn) and rainbows, the only thing close to ambiguous about this is that he isn't human.
- Catchphrase: "Hi, I'm Hugh Bliss!" *ding!* (wiggles fingers in an arc)
- Church of Happyology: His book is titled Emetics, and true to the meaning of the word and the beliefs espoused within, the cover depicts someone happily vomiting a rainbow.
- Creepy High-Pitched Voice: He has a rather effeminate high-pitched voice, which combined with his Dissonant Serenity, as well as being albino, lend him an air of creepiness, which turns out to be fitting when he is revealed as the Big Bad of Season 1.
- Devil in Plain Sight: He's Roy G. Biv, the mastermind behind the events of season 1. You can tell immediately that the rainbow-themed Hugh is Roy G. Biv's real identity since the name stands for the seven colors of the rainbow. The joke around this comes in the episode after it's revealed, where Sam quickly figures out the connection...but through exceedingly complex Insane Troll Logic, and it's treated a big revelation.
- Easily Forgiven: Inverted in that it's HE who easily forgives Sam and Max. In 205, when he is encountered in hell, he refuses to talk to them at first, until you select the "I'm sorry" dialogue option. Afterward, he'll chat away like nothing ever happened.
- Even Evil Has Standards: Found the contents of Max's mind to be unspeakably depraved.
- Giggling Villain: He's constantly launching into the creepiest tittering.
- Head Turned Backwards: When you talk to him in season 2, rather than getting up from his chair, he just twists his head around backwards to look at Sam & Max.
- Nightmare Fuel Station Attendant: He's just creepy, and not just about his worrying levels of happiness, either. In "Abe Lincoln Must Die!", using The Bug on him results in him monologuing...only for him to say he knew they were listening the whole time. That's not even getting into the fact that he's the Big Bad of season 1 and a colony of sentient germs.)
- The Worm That Walks: Turns out he's a colony of germs.
- And I Must Scream: See, after every episode, Sam and Max would put an artifact from the last episode into their closet. After the third episode, they put Leonard in the closet, tied up with his mouth taped shut. It's implied that he's been living in that closet for months! Max also makes an off-hand comment that he remembers to feed Leonard regularly...with spiders and the deed to the United States. Eventually he dies, but just ends up in an identical closet in Hell. Luckily for him, he shared his personal hell with Sam who, out of pity, releases him...with his mouth still taped shut. Evidently, Telltale felt sorry for him and decided to finally release him.
- Disproportionate Retribution: Apparently being told "yo momma" jokes about his beloved mother and being stuffed in a closet and fed nothing but dirt and spiders is Sam and Max's idea of just punishment for stealing a sandwich.
- Even Bad Men Love Their Mamas: Sam and Max break his spirit doing the interrogation by telling "yo momma" jokes.
- The Informant: but only once.
- Reused Character Design: He is basically Boris Krinkle from Telltale Texas Hold'em, but with a handlebar mustache. It is even lampshaded a couple of times.
- Smug Snake: He's pretty proud of his winning streak, especially considering he's a cheater. Once he loses, though...
- Younger Than They Look: The carbon-dater in Lincoln Must Die says he's actually only 19, and apparently he looks so much older because of a life of hard gambling.
Shambling Corporate PresenceA demon who debuted in "Reality 2.0", but doesn't make its first visual appearance until "Ice Station Santa".
- Blob Monster: He's a blue, gelatinous thing with amoeba-like tentacles and Extra Eyes. Max compares him to a "latex glove full of jelly".
- Early-Bird Cameo: He debuts in "Reality 2.0" as a minor antagonist, but only in a text adventure sequence with no graphics. He doesn't visually appear unti "Ice Station Santa".
- Immune to Bullets: Shooting it is pointless due to its amorphous composition.
- The Slacker: Spends all his time in Hell playing Minesweeper instead of working.
- The Unintelligible: It's only able to speak by saying "Blarg".
- Ambiguously Gay: Max calls him "fruity" in Night of the Raving Dead, and probably for a reason.
- Agent Peacock: He apparently beats Sam and Max in a fight, and throws Sameth and Maximus out of his train room while still human.
- Catchphrase: "Yeeees?"
- Evil Redhead: Zigzagged. While he has blood-red hair as a vampire, his natural hair color is actually black. But he had sandy blonde hair when he was still a mortal.
- Evil Sounds Deep: Hes got a fairly deep and smooth voice, complimented by his accent (which is funny considering that hes voiced by William Kasten, who also voiced Max.)
- Gratuitous German: While not present in his first appearance in "Night of the Raving Dead", in "The Tomb of Sammun-Mak", this trope is in play. Justified in that he's a native of Stuttgart and this was when he was much younger and probably still learning how to speak English.
- Goth: While he definitely fits the bill in "Night of the Raving Dead", no longer so in "The City That Dares Not Sleep"; he is once again wearing the attire he wore in "The Tomb of Sammun-Mak", stating that "Goth was so three years ago", and that early 1900s fashion is the new style to go.
- Jerk with a Heart of Jerk: Think he might have been a decent person before he became a vampire? Guess again. "The Tomb of Sammun-Mak" reveals he was always a nasty guy.
- Older Than They Look: True, this trope is in effect by default by being a vampire, but when he was still a mortal, he spent 50 years stuck on an ancient Egyptian wall as part of a curse and didn't age a single day when Sameth and Maximus free him. So he would be, chronologically speaking, around 70 to 80 years old when he became a vampire, but still with the body of a 20-something.
- Our Vampires Are Different: In this case, they're campy, contagious, and gain power from admiration in addition to blood.
- Popularity Power: A literal example. He gains power by following trends and gaining the approval of his followers.
- Sassy Secretary: Like all of the other villains that die in seasons 1 and 2, we see him working for Hell. He's forced to work as the secretary in Hell's foyer and act as Satan's assistant. He's understandably unhappy with Sam and Max for putting him into this situation.
- Smug Snake: A scheming bad guy, but never impressive.
- Super Reflexes: Probably his only true fighting skill. He's fast enough to snatch Sam's bullets out of the air and effortlessly swat vampire-killing wooden stakes out of peoples' hands. Only Jesse James' hand is fast enough to keep up with him.
- Vampires Own Nightclubs: He turned his castle into a dance club called the Zombie Factory.
- Vampires Are Sex Gods: He's even more "tragically sexy" to Nefertiti after he's turned.
- Affably Evil: Pedro is very friendly, polite, easy-going and reasonable fellow. If it weren't for the whole "harvesting souls of Hell" thing, he'd be an unabashed Nice Guy, and even with that detail, it's hard to really get upset with him.
- Deal with the Devil: Literally; to pay for their time-traveling spaceship, Pedro became an outsourced soul-collector for Hell and asked their new boss to cosign the loan.
- Fun with Acronyms: "T.H.E.M" turns out to not only be Bosco spelling "Them" out of fear, but an actual acronym for Pedro's little organization: the Temporal Headquarters of Enlightened Mariachis.
- Future Me Scares Me: Well, more like annoys. Young Pedro dislikes both of his elderly counterparts and thinks they are holding him back; he wants to abandon the birthday singing gig to try and make it as a solo singer.
- I Hate Past Me: Young Pedro is, frankly, a jerk, and a conversation with Elderly Pedro has him reveal that it really irks him that he's stuck managing the soul-crushing & delivery system and being a general handyman whilst Young Pedro has appointed himself the captain.
- Stereotype Reaction Gag: After first meeting the three Pedros, when Sam & Max first approach Elderly Pedro and Sam address him as Pedro, the Mexican mariachi angrily dresses Sam down for stereotyping... then, when Sam apologizes, he laughs and admits that he was kidding, as Pedro is his actual name.
- Undignified Death: Elderly Pedro learns that he is forecast as dying due to inhaling printer ink fumes, which he angrily notes is a stupid way to die.
- Well-Intentioned Extremist: Pedro just wants to bring everyone in the world delight by playing mariachi music for them on their birthdays. In pursuit of this goal, he's willing to take on a temporary contract harvesting souls for Hell.
The Soda Poppers
- Big Bad Triumvirate: Of Season 2.
- Catch Phrases:Specs: You made me mess up!
Peepers: I can see you!
Whizzer: Time out for number one!
- The Chew Toy: All three often wind up at the end of some form of comic abuse by Sam and Max in each episode they appear in, even before the two start getting annoyed by the trio. This doesn't end even after it's revealed they've been evil the whole time.
- Cruel and Unusual Death: In the epilogue for season 2; after vowing they'll return, the lava from "Moai Better Blues" rains down on them and they burn up into nothing, screaming briefly in pain before they melt away, leaving only Peepers' disembodied eyeballs floating along in the lava.
- Evil Costume Switch: Peepers and Whizzer's costume change simply consists of their regular costumes recolored in black with some flame decals added. Specs, however, shows up wearing an SM-style mask and pair of pants in black leather with decorative spikes and criticizes his brothers for their lack of imagination.
- Evil Is Petty: Their primary reason for wanting vengeance on Sam & Max is give as the duo's disruption of their birthday during the events of Season 1.
- Eye Beams: Peepers gains the powers to fire these when he becomes a demon prince at the end of episode 205.
- Fantastic Drug: Soda Pop is treated as being this for Whizzer, with a critical quest even requiring that Sam & Max force him back off the wagon he tries to get over his addiction.
- Former Child Star: While they still look like children, their careers peaked then crashed in the 1970s.
- From Nobody to Nightmare: Go from being the unwitting pawns of Brady Culture, the villain in episode 1 of Season 1 to the leaders of Hell and the Big Bad Triumvirate of Season 2. They even have Brady and Hugh Bliss, the latter the Big Bad of Season 1, under their thumb.
- Men on Fire: After falling into a lava pit, they swear to meet Sam and Max again, only to be burned alive by the lava transported at the end of "Moai Better Blues".
- Neat Freak: Specs. His perfectionism even applies to graffiti.
- Older Than They Look: They are forty-somethings who look like eight years old.
- However, if you look closely at their faces during conversations, you can clearly see they all have five o'clock shadows. Whizzer also has a bad case of male pattern baldness as well.
- Potty Emergency: Whizzer's shtick, as his nickname and catchphrase indicate. It's a side-effect of his addiction to soda pop, and he does start to get over it when he manages to get off the pop... until Sam & Max force him off the wagon again.
- Sibling Rivalry: When they get into politics, it escalates into Civil War.
- Start of Darkness: Beating Brady Culture to death shortly after "Culture Shock".
- Theme Tune: More Than Jerks, an instrumental version of which is also used as the driving theme for the first two seasons.
- Unfortunate Names: One quest in "What's New, Beelzebub?" involves finding out that Peepers's real name is Dick Peacock, not that the trio's nicknames are any better.
- Urine Trouble: Whizzer's power as a Demon Prince is to spray flaming urine at his foes.
General Skun-ka'peBig Bad of Season 3, Skun-ka'pe comes to Earth looking for the Toys of Power so he can take over the galaxy. Not the main villain, but he shows up enough times to be a really big pain in the ass. Has a really good talent for getting gullible people to help him, but also has many spots of gullibility of his own, particularly where the aforementioned Toys are concerned.
- All There in the Manual: Sam & Max Secret Origins: Skun'kape details his childhood and career prior to the third Season, revealing his motivations and real name (Arthur J. Thompson).
- Arc Villain: Of "The Penal Zone".
- Bad Liar: Makes a pathetically token attempt to hide his true intentions in his first appearance.
- Big Bad Duumvirate: Forms an alliance with Papierwaite to gather all the Toys of Power within the Devil's Toybox, using a combination of his technology and Papierwaite's magic. Breaking this compact is the only way to move forward in the episode.
- Cold Ham: Frequently speaks in a low, subdued manner, rarely ever yelling unless particularly aggravated. He also makes a number of grandiose movements and gestures.
- Freudian Excuse: His childhood, as shown in Sam & Max Secret Origins: Skun'kape, really kind of sucked.
- From Nobody to Nightmare: He was originally just an oft-bullied child with an interest in comic books, but after getting fired from his job at a factory, got a wire from one of the machines stuck in his head, which made him psychic and allowed him to take over his home planet with relative ease.
- Obviously Evil: As Max says, he makes his appearance on Earth in a giant warship shaped liked his own head, with laser-beam eyes. It's not hard to connect the dots from there.
- Screw This, I'm Out of Here!: After everything he gets put through in The Devil's Playhouse, the only thought on his mind is getting as far away from Earth as he possibly can. Unfortunately, Max had other ideas...
- Suspiciously Specific Denial: Ties into Bad Liar.Skun-ka'pe: On every planet I visit, all of the local mole people are invited to ride my fantastic gamma beam to a wonderful off-world vacation they'll never forget! (beat) ...I don't kill them.
- Villain Decay: While the main villain and a serious threat for the first episode of Season 3, by Beyond the Alley of the Dolls he has been reduced to whimpering in a corner in Stinky's Diner and is quickly taken out by the Sam clones early on in the episode.
Monsieur Anton Papierwaite
- Arc Villain: Of "The Tomb of Sammun-mak".
- Badass Bookworm: Papierwaite is kind of dorky, but he's skilled in all manner of dark magic.
- HeelFace Turn: In "Beyond the Alley of The Dolls", it's revealed that he's been trying to destroy the Devil's Toybox since his defeat in "The Tomb of Sammun-mak".
- Evil Is Hammy: He's not the hammiest character by a long shot, but just listen to him talk about the Dark Dimensioooon! The others are never particularly impressed.Papierwaite: If that monkey dares touch my tapestry, he shall feel my hot, explosive wrath!
Max: Yeah, just keep your hot wrath off my jar. Takes forever to clean.
- Evil Sorcerer: Shows himself to be quite skilled with magic after merging with Yog-Soggoth.
- Humanoid Abomination: Sort of. Doctor Norrington AKA Yog-Soggoth is apparently merged with Papierwaite's body after his defeat at the end of The Tomb of Sammun-Mak.
- Motor Mouth: If you get him started on one of his favorite subjects, especially Yog-Soggoth, he will not stop gushing about it. Even Yog-Soggoth himself gets fed up with him.
The Pharaoh Sammun-Mak
- Arc Villain: Of "They Stole Max's Brain".
- Attention Deficit... Ooh, Shiny!: His greatest weakness.
- "Attention everyone! From this point forward, those little things at the end of your shoe laces, ag...lets? Yes! Aglets are hereby decreed to be the most horrible things in all the world!"
- "Attention everyone! This is Sammun-Mak, Lord of all Creation! Forget what we said before! From now on, toasters are officially the most horrid, beastly things in the whole wide world! And if you see a toaster, and you want to make us happy, break it into tiny little bits!"
- "Greetings, everyone! This is Sammun-Mak the Divine speaking! From this day forward, toasters are the most exalted things in all the universe, ranking just below yours truly on the awesome-meter! Just thought you should know."
- All of the above happens within a matter of minutes.
- When back in "The City That Dares Not Sleep" on Skun'ka-pe's flagship, he is having trouble controlling his thoughts enough, having to tell Sam to stop talking about a certain thing to keep himself from diverting his attention towards said object. Sam still manages to eventually outsmart him by saying "Rabbit Season".
- Bratty Half-Pint: It takes about three minutes for his squeaky-voiced arrogance to get annoying. Very very annoying.
- Brain in a Jar: Twice; once not long before his death, and second after Sam stabbed him with the Brain Screw,
- Enfante Terrible: To homicidal, tyrannical levels.
- Family-Unfriendly Death: He's ultimately defeated (for the second time) when Max tricks Sam into stabbing him in the face with the Brain Screw. His brain survives a little longer, only to be blown up a week later by Giant Max's explosion
- Finders Rulers: A variation. He only became Pharaoh because he had the Gift, and, using the Devil's Toybox, altered reality so that he was in a position of power. He does the exact same thing a thousand years later.
- 100% Adoration Rating: Due to brainwashing, although the mole people and Max were immune.
- Nepharious Pharaoh: Despite his young age, his god complex and Psychic Powers make him a serious menace provided he can stay focused for more than a few minutes.
- Not So Different: He is very similar to Max: Egotistical, enamored with violence, detached from reality, and a short attention span. All he has on Max is a larger vocabulary and a justified god complex.
- Royal "We": Almost always refers to himself with the first-person plural, to Sam's annoyance.
- Sixth Ranger Traitor: It looks like Sammun-Mak is slated to become a protagonist or at least a sidekick, given that he is in control of Max's body for a little while. Then he catches sight of the gradually-filling Devil's Toybox, and things go way south from there.
Clone Master/Charlie Ho-TepBig Bad of "Beyond the Alley of the Dolls", Charlie Ho-Tep is one of the Toys of Power, the one that enables ventriloquism. He was played with by Junior, the first owner of the Toys of Power, for one hour before being discarded. In the present, he brainwashes Sal and Girl Stinky and uses Mamma Bosco's cloning technology to create the Samulacra so he can find the Toys of Power.
- Actually Pretty Funny: When Max uses Psychic Ventriloquism on the Statue of Liberty to use his voice for a voting joke, he'll admit it's "funny stuff", although he says he's an anarchist.
- Arc Villain: Of "Beyond the Alley of the Dolls".
- Berserk Button: Do not mention that Junior never loved Charlie. He'll drop everything he's doing just to rub you out.
- Chekhov's Gunman: What seemed to be just a psychic toy item turns out to be one of the game's major antagonists.
- Climax Boss: The fourth episode, in general, clarifies most of the backstory of the Devil's Toybox, the game's Plot Device. His defeat is caused by the box being destroyed.
- Creepy Doll: He was this even before The Reveal.
- Demonic Dummy: It's a toy that belongs to an ancient Eldritch Abomination.
- The Dog Was the Mastermind: Who could have guessed that the mastermind behind the clones was actually Charlie Ho-Tep, or that an item used by Max was actually sentient the whole time?
- The Friend Nobody Likes: Almost nobody who picks up Charlie Ho-Tep wants anything to do with him, to the point where he's the only Psychic Toy that Max attempts to reject entirely. This even extends to his Freudian Excuse as even Junior considered him to be creepy and his least favorite toy.
- Freudian Excuse: His entire reason to be as a toy is to be played with. However, Junior played with him exactly once for an hour before shoving him back into the Devil's Toybox and never doing so again because he was too creepy for the young Eldritch Abomination. He spends the entirety of his speaking screen-time ranting about memories of that hour as if it was years instead, obsessed with summoning Junior back from the Dark Dimension to play with him again.
- Hive Queen: To the Doggelgangers.
- Punny Name: Almost sounds like Nyarlathotep.
- Undignified Death: He spends his entire death sequence whining about Junior putting him back in the box and screaming "WHY WON'T YOU PLAY WITH ME?" before exploding. Max even Lampshades it.
Samulacra (or Doggelgangers)
- Doppelgänger: To Sam, due to cloning.
- Fan Disservice: Naked except for golden shorts. Sam's rather embarrassed about this.
- Felony Misdemeanor: One of them swipes Sam's hat, and Sam has a grudge against him for the rest of the episode.
- Hive Mind: They seem to have very little capacity for independent thought and are controlled by either a microphone in Bosco-Tech's sub-basement or directly by Charlie Ho-Tep's piano. Attempting to use the Mind Reading power on them results in Max getting a Poke in the Third Eye as he get bombarded with every one of the over a thousand clones mentally chanting "Toys!" at the same time.
- Insistent Terminology: A Running Gag throughout "Beyond the Alley of the Dolls" is that Sam and Max can'ta gree on what to call them. Sam calls them "Samulacra", while Max adamantly calls them "Doggelgangers". Both refuse to budge on their decisions.
- Even the dialogue wheel gets in on this, as the first option when speaking about them to another character is always "Samulacra" and the second is always "Doggelgangers".
- Kick the Dog: The aforementioned beloved Plushie Clone is the second victim of Monster Max's rampage.
- "Not Wearing Pants" Dream: Upon seeing the first clone enter the room at the end of "They Stole Max's Brain," Sam comments "This is just like that dream I had last night. I hope he studied for his finals..." Considering how the clones are dressed, we can safely assume Sam has nightmares about being in public in his underwear.