Voiced By: Dominic Armato (The Curse of Monkey Island, Escape from Monkey Island, Tales of Monkey Island, The Secret of Monkey Island: Special Edition, Monkey Island 2 Special Edition: LeChuck's Revenge)
The main hero of the Monkey Island series, Guybrush Threepwood is a likable young man who in the first game desperately wants to be a pirate. Unfortunately for Guybrush he does not have the general demeanor of a pirate, and has to get by using his quick wits to solve problems. During his pirating career Guybrush has managed to accomplish several impressive pirating feats, but no one ever gives him credit for anything he does and they treat him like a child trying to play pirate.Guybrush's wanting something is always the main thrust of the series. In the first game he wanted to be a real pirate and impress, and then save, Governor Elaine Marley; in the second game he looked for the legendary treasure of Big Whoop; in the third game he wanted to find a ring to undo a curse on his now fiancée Elaine; in the fourth game he wanted to find the Ultimate Insult to save the Caribbean; and in Tales he wanted to find a cure for the Pox of LeChuck.Nothing much is known about Guybrush before he washed up on Melee Island. LeChuck's Revenge heavily implied in the ending that he had a mother and father who disappeared and a brother named Chuckie, but that ending has since been retconned as a magic-induced dream, so how much of it is true is questionable. For current family he is Happily Married to Elaine Marley.Interestingly, the name 'Guybrush' was largely an accident — Steve Purcell saved his design of the unnamed main character as 'guybrush' in D-Paint; 'guy' since they hadn't come up with a name for him yet, and 'brush' to indicate this was the brush file. They started referring to the main character as "Guybrush", and it snowballed from there.
Accidental Misnaming: Almost everyone who tries to call Guybrush Threepwood by name. Including himself in chapter 4 of Tales, which is something of a first.
An Arm and a Leg: Morgan LeFlay cuts off his pox-ridden hand in Chapter 2 of Tales and he only gets it restored at the very end of Chapter 5.
Animal Talk: Guybrush talks to dogs... by speaking in the language of dogs! Such is the case with Spiffy in Secret and Old Blind Pew in Curse. He even talks to monkeys, like Jojo Jr. (who not only understands human language, but also learned to speak in said human language too!) in Escape, and Jacques (who also understands human language) in Tales. In Chapter 3 of Tales, there are manatees that speak in their own language that Guybrush is not good at understanding. He discovers that he needs to be a successor to Santino by getting the manatee language book from the Marquis De Singe via the Voodoo Lady, and by getting the Tongue of the Manatee. Once Guybrush obtains both, he can communicate with the manatees in their own language, while the subtitles act as interpreter for the manatee language, regardless of whether you've turned them on or off.
Badass: Despite everything about him, Guybrush has managed to survive against impossible foes to become one of the most famous pirates in the seven seas without resorting to violence as a first resort, but is a competent enough fighter to survive going one-on-one with Morgan LeFlay.
Badass Beard: Is sporting one in Tales. It's what convinced Winslow that he would make a great captain.
Badass Normal: When he isn't using some sort of voodoo spell to help him out.
Badass On Paper: If you were to read everything Guybrush has achieved in the space of five games you'd expect him to be the most badass pirate that has ever sailed (found the legendary treasure of Big Whoop, repeatedly defeated the dread undead pirate captain LeChuck, the only man to ever escape the Carnival of the Damned intact, etc.). If you were to spend the same amount of time playing as him, well...
It is suggested he has quite a reputation. Among pirates who've never met him, at least. There's even a chain of theme restaurants based on him.
Buffy Speak: Guybrush tends to say it whenever he comes across something he hasn't named yet. This happens quite a lot in Tales.
Hook Hand: Gets a pretty useful one in episode 2 of Tales, after Morgan cuts off his poxed left hand.
Idiot Hero: He's sort of clownish, but people tend to underestimate him.
Iron Butt Monkey: Takes ridiculous amounts of punishment up to and including being killed, generally in amusing ways.
Guile Hero: He has a razor sharp wit, and usually defeats his opponents by outsmarting them. Also, while he may lack common sense and a complete educational background, he is much smarter than a majority of the characters in the series. He is also highly literate, able to read long passages of literature and pronounce extremely complex words and phrases without having to think about it or sound it out, which is surprising, as Guybrush mentions several times throughout the series that he dropped out of college and most pirates lack conventional skills in areas of schooling.
Master of Unlocking: From Chapter 2 of Tales onward, Guybrush can use his hook hand as a lockpick to unlock doors and treasure chests. Of course, there are only a few items that can't be unlocked by his hook alone, and that is in the final chapter.
Older than They Look: He has trouble getting service in reputable bars because he looks like a teenager. Fortunately, such establishments are uncommon in the Caribbean. It's not clear how old he actually is, just that it's older than he looks.
Talking to Himself: Dominic Armato, Guybrush's voice actor, also does the Duck in Escape and the Pyrite Parrot of Petaluma in Tales.
Took a Level in Badass: Zigzagged, as his goofiness sometimes gets in the way, but still present since he starts his journey as a pirate wannabe. He's usually trashed in the first act of a given game, only to become wiser and more powerful as the story goes by, usually with the help of some artifact or with some Level Grinding involved. And it takes guts to share a room with LeChuck.
Took a Level in Jerkass: In LeChuck's Revenge he is noticeably more egotistical and meaner than in Secret, proud of his previous defeat of LeChuck and trying to act more like a real pirate. This leads to Elaine breaking up with him prior to the game.
The Trickster: How he defeats his stronger and tougher opponents.
(Ex-)note As of EscapeGovernor Elaine Marley-Threepwood
Voiced By: Alexandra Boyd (The Curse of Monkey Island, Tales of Monkey Island, The Secret of Monkey Island: Special Edition, Monkey Island 2 Special Edition: LeChuck's Revenge); Charity James (Escape from Monkey Island)
The much beloved governor of the Tri-Island Area, specifically Melee Island, Booty Island, and Plunder Island. Elaine Marley first met Guybrush Threepwood when he was working to complete his three pirate trials on Melee Island. It was Love at First Sight. Before that happened though Elaine had rejected the advances of the Pirate LeChuck, who came back and kidnapped her, prompting Guybrush to mount a rescue mission to Monkey Island. His efforts proved pointless, as Elaine had defied the usual Damsel in Distress stereotype by escaping and coming up with a plan to destroy LeChuck, which failed.Since then Elaine has been the center of a Love Triangle between herself, Guybrush, and LeChuck. She grew closer to Guybrush while fending off LeChuck's advances/kidnappings. Elaine and Guybrush eventually got engaged and married in Curse, which did not deter LeChuck in the slightest. Between Guybrush and Elaine it is obvious that Elaine is the one that wears the pants in the relationship.At the end of Escape Elaine renounced her governorship so she could sail around the Caribbean at her leisure with Guybrush.
The Ace: She's good at everything. The games would be very short if only Guybrush knew how to stay of out trouble.
Voiced By: Earl Boen (The Curse of Monkey Island, Escape from Monkey Island, Tales of Monkey Island, The Secret of Monkey Island: Special Edition, Monkey Island 2 Special Edition: LeChuck's Revenge), Kevin Blackton (Human LeChuck in Tales of Monkey Island)
The Big Bad of the series, LeChuck is obsessed with taking over the Caribbean and marrying Elaine Marley. Before the start of the series LeChuck went off to find the legendary treasure of Big Whoop in order to impress Elaine. Big Whoop turned out be a portal to Hell that transformed him into a demon capable of summoning the undead to serve as his crew, as well as a bunch of other powers such as flying and shooting fire.Every game so far has had him try to take over the Caribbean in some way, usually with a type of voodoo weapon. And every time, Guybrush Threepwood has stopped and killed him. But since he's already undead LeChuck always manages to come back in some form. The only exceptions to this were in LeChuck's Revenge when he was specifically targeting Guybrush, and in Tales, when he finally succeeded in turning the tables around and killing Guybrush in an ambush thanks to some voodoo trust charm the villain had worn when he was human; for a short while he emerged victorious... until Guybrush managed to come Back from the Dead in order to stop him once and for all.Despite the more comical aspects of his personality LeChuck is considered very dangerous by other pirates. He sees Guybrush as his greatest enemy.LeChuck's apppearance has changed with each game. In Secret he appeared as a ghost; in Revenge he was a zombie; in Curse he looked like a demon; in Escape he could change his appearance between the three at will; and in Tales he alternates between zombie and demon.
Beard of Evil: LeChuck's beard is very impressive, whether it's ghostly and wriggling, zombiefied and slimy, or formed from the very flames of Hell itself. Mostly it hides the fact that from the third game onward LeChuck has a really tiny head.
Beware the Silly Ones: For most of the series LeChuck may seem cartoonishly over-the-top, but let's not forget that he acquired his original ghost crew by sacking a pirate ship and murdering the entire crew. Kind of puts it into perspective when he's making ridiculous threats and spending entire acts failing to kill Guybrush.
Big Bad: Except in Escape where, in a surprise twist, he's revealed to be The Dragon to the game's real main villain, Ozzie Mandrill.
Ninja Pirate Zombie Robot: LeChuck has, by the end of Tales, been a human pirate, a ghost pirate, a zombie pirate, a demon pirate, a living statue pirate, a giant walrus pirate (not shown in any game yet, but mentioned in Tales), a demon pirate again, a human pirate again, and a demon pirate god.
Not-So-Harmless Villain: He is quite dimwitted, but makes up for it by being very evil. He displays an extreme fondness for horrible torture, is a mass murderer, and he has vast voodoo powers and nearly endless hoard of undead crewmen.
The Other Darrin: Full circle. Goes from Earl Boen to Adam Harrington to Kevin Blackton and back to Earl Boen.
Talking to Himself: Adam Harrington, The Other Darrin for LeChuck in the PC download version of Chapter 1 of Tales, also does the voice for "Moose" Muszalski in Chapter 3, though the two characters have never met each other.
Voluntary Shapeshifting: In the first game he effortlessly passes as a living human. By the fourth game he can transform between his ghost, zombie and demon forms at will.
The Voodoo Lady
Voiced By: Leilani Jones (The Curse of Monkey Island, Escape from Monkey Island, The Secret of Monkey Island: Special Edition, Monkey Island 2 Special Edition: LeChuck's Revenge); Alison Ewing (Tales of Monkey Island)
The resident Ms. Exposition of the series, the woman only known as The Voodoo Lady has appeared in every game to give Guybrush and the player an overview of what Guybrush will do over the course of the game, though in a vague way that most likely will not make sense to the player the first time around. In Secret it was completely optional to visit the Voodoo Lady, but in subsequent games it is impossible to proceed unless Guybrush goes to her place to learn what to do. Half the time Guybrush visits her to procure some voodoo item he needs to complete a puzzle.Little is known about her past. She always manages to have a store on one of the islands Guybrush goes to per game, and her knowledge of voodoo lore is very extensive. Tales revealed some information about her past. In the past she was in a relationship with Coronado De Cava, who went off to find La Esponja Grande for her and disappeared. In "The Trial and Execution of Guybrush Threepwood" LeChuck accuses her of manipulating the events of the entire series, including his own actions, an accusation which she denies. It is unclear if anything LeChuck says is true, since accusing the Voodoo Lady and getting her thrown in jail furthers his own plans to rule the Caribbean. At the end she is shown grinning evilly over LeChuck's voodoo essence, so it remains to be seen if she is evil.
Ascended Extra: In her first appearance, she was a side character that you could go the entire game without meeting. She plays a major role in the sequel, and goes on to become a staple character in the rest of the series.
Big Good: As she gives Guybrush the various items he needs to defeat LeChuck, and is in general dedicated to preserving the harmony of the natural order...
Bigger Bad: However, LeChuck claims that she has been manipulating him and Guybrush all these years for some nefarious purpose, and the end of Tales has her chuckling evilly after gaining a jar containing LeChuck's voodoo essence. Elaine certainly believes LeChuck's claim, but Guybrush isn't so sure.
Talking to Herself: The Voodoo Lady's voice actress, Leilani Jones-Wilmore, does the voice for Carla the Swordmaster in the Special Edition of Secret, while her other voice actress, Alison Ewing, does the voice for Bosun Kathryn Krebbs in Tales, though all three of these characters have never met each other.
Themed Tarot Deck: Has a set in Tales which she narrates the events of the previous chapter.
Witch Doctor: She can create lots of voodoo trinkets, but her specialty is voodoo dolls.
Smilin' Stan S. Stanman, or just Stan
Voiced By: Pat Pinney (The Curse of Monkey Island, The Secret of Monkey Island: Special Edition, Monkey Island 2 Special Edition: LeChuck's Revenge); Pat Fraley (Escape from Monkey Island); Gavin Hammon (Tales of Monkey Island)
A salesman that Guybrush runs into in each game. In Secret Stan sold previously-owned ships, in Revenge previously-owned coffins, in Curse life insurance, in Escape time shares, and in Tales memorabilia of Guybrush's trial while acting as the prosecution. The quality of the items Stan sells is always questionable, but Guybrush always tricks or rips him off anyway, so it evens out.
Talking to Himself: Besides Stan, his voice actor Pat Pinney does the voices of Elaine Marley's grillcook and the moose in the Special Edition of Revenge, though neither character has met with each other.
Unmoving Plaid: It's so iconic that even in the 3D games, the animators went out of their way to get his jacket to maintain an Unmoving Plaid pattern.
Voiced By: Neil Ross (The Curse of Monkey Island, Monkey Island 2 Special Edition: LeChuck's Revenge)
A cartographer Guybrush meets on Scabb Island in Revenge. Wally helps Gubyrush reassemble the map to Big Whoop, and is later kidnapped by LeChuck to prevent Guybrush from finding the treasure. Guybrush sneaks into LeChuck's and rescues Wally, but they get separated when Guybrush blows up LeChuck's fortress.Wally reappears in Curse, working for LeChuck as the dreaded pirate Bloodnose. Wally is the one that tells Guybrush the engagement ring he gave to Elaine is cursed, after she had already put it on. He is last seen in LeChuck's Carnival of the Damned as one of the attractions.Wally is the most innocent character in the series, which is why the developers had so much fun torturing him.
Badass Bookworm: Wally both subverts this and plays it straight when he's "Bloodnose".
Blind Without 'Em: He cannot see a thing without his monocle. Too bad Guybrush has to steal it to complete a puzzle.
Talking to Himself: Neil Ross, Wally's voice actor, does the voices of Rum Rogers, Jr. and Filbert the Gardener in the Special Edition of Revenge, and Hugo the Perfume-Spritzer and Pirate #4 in Escape, though neither characters have talked to each other.
Voiced By: Denny Delk (The Curse of Monkey Island, Escape from Monkey Island, Tales of Monkey Island))
Murray the Demonic Talking Skull was a member of LeChuck's undead pirate crew with dreams of World Domination. Guybrush blasted Murray and his crewmates with a cannon in order to save Elaine, reducing him to a skull. Murray appears throughout Curse, going on at length about how he will take over the world with his legion of the damned. Despite destroying his body Guybrush gets along well with Murray.Murray makes a cameo in Escape as a bouncer at Planet Threepwood, and has a more important appearance in Tales.
Ascended Extra: Murray's appearance in initial test versions of Curse were so popular with the playtesters that he was given more appearances throughout the game.
Talking to Himself: Besides Murray, his voice actor does Skully and the Father Pirate in Curse; Mister Santiago in Escape; one of the Pirate Leaders, the Narrator, and the Citizen of Mêlée in the Special Edition of Secret; and Fred (the Man of Low Moral Fiber), Bruno, Larry, the Narrator (again) and the Voodoo Priest in the Special Edition of Revenge. Neither character has ever met each other.
Throw It In: Most of his dialogue in Curse was improvised by his voice actor, who just decided to Chew The Scenery and play it for laughs.
Voiced By: Cam Clarke (Escape from Monkey Island, The Secret of Monkey Island: Special Edition)
Meathook is one of the people Guybrush recruits for his crew to sail to Monkey Island to look for Elaine. Like the rest of the crew he mutinies and ends up stranded on Monkey Island. He returned in Escape, having made it back to Melee Island, where he started a career in wax paintings.Meathook has two hooks for hands, is bald, wears an eyepatch, and has a skull tattoo on his chest that he can make talk. Meathook lost both his hands to a "terrifying creature" that Guybrush has to touch to get Meathook to join his crew. It's a parrot.His house is the one that you need the rubber-chicken-with-a-pulley-in-the-middle to get to.
Voiced By: Wally Wingert (Escape from Monkey Island, The Secret of Monkey Island: Special Edition, Monkey Island 2 Special Edition: LeChuck's Revenge)
Herman Toothrot is a hermit Guybrush meets when he first arrives on Monkey Island. Herman originally found Monkey Island on the Sea Monkey with his crewmmate, who later accidentally hung himself. He helps Guybrush out by explaining various places in Monkey Island, assists him with some puzzles involving the Monkey Island Cannibals, and is possibly the one who give him a ride back to Melee Island.Herman make small cameos in Revenge and Curse, then makes an important return in Escape, where his backstory is Retconned into being the grandfather of Elaine Marley. At the end of Escape he takes the job of Governor back from Elaine, allowing her to sail the high seas with Guybrush.
Continuity Snarl: The only way his backstory makes sense is if he was knocked into the whirlpool by Ozzie Mandrill, washed up on Monkey Island, got amnesia, got off of Monkey Island, went to Melee Island, bought the Sea Monkey so he could return to Monkey Island for whatever reason, got a crewmate, returned to Monkey Island, and lost his ship and crewmate.
Talking to Himself: Besides Herman, his voice actor Wally Wingert does the voices of two other pirates in Escape; Biff the Ghost and one Insult Swordfight opponent in the Special Edition of Secret; the Potman and Greg in the Special Edition of Revenge; and Franklin (the Man of Low Moral Fiber) in both latter games. Neither of them have ever met each other, however.
Largo LaGrande was LeChuck's second-in-command when he was alive. After he died Largo moved to Scabb Island, where he used his status as LeChuck's second-in-command to bully the island populace. Guybrush eventually drives off Largo, but not before he steals LeChuck's beard from Guybrush, which he uses to resurrect LeChuck. Afterward he only appears to get berated by LeChuck, and disappears after Guybrush blows up LeChuck's fortress. He hasn't been seen since.
0% Approval Rating: He is the head of Scabb Island, but only because he bullies everyone else, and is hated by everyone in turn.
Talking to Himself: In the Special Edition, we hear Largo LaGrande berate Mad Marty after the Bucket of Mud incident, which is very odd because both characters are voiced by James Arnold Taylor; in other words, it sounds more like Taylor is chiding himself! Besides these two, Taylor has also provided voices for the Spitmaster and the Fisherman, and that's pretty much it.
Villainous Crossdresser: Implied. Guybrush needs to steal a bra that belongs to him from the laundrymat, though we never actually see him wear it.
Voiced By: Jared Emerson-Johnson (Tales of Monkey Island)
The other villain of Tales, the Marquis De Singe is a Mad Scientist conducting experiments on Flotsam Island, using a wind machine to bring new test subjects to the island. When De Singe sees that Guybrush's hand has been cursed with the Pox of LeChuck, he suspects that it may contain the secret of immortality and tries to remove Guybrush's hand. He succeeds and creates an immortality elixir out of the Pox, but discovers that the elixir only works for so long. To fix that, De Singe tries to pulverize Elaine Marley-Threepwood, who had already been infected by the Pox, and spread her ashes into the atmosphere, infecting everyone in the planet so he will have enough subjects to make elixir out of.In the end he is stopped by Guybrush, who destroys the machine in the turban that was sucking the Pox out of his hand, which in turn knocks De Singe into his wind machine, pulverizing him into dust.
Sissy Villain: He is not one of the strongest opponents, which is why he relies on tools and machines.
Talking to Himself: Jared Emerson-Johnson, De Singe's voice actor, has also provided the voice of one of McGillicutty's crew members of the Spoon Isle Trio, though the two have never met.
Unexplained Accent: Played with, when De Singe is offended at the implication that he's French. Even though he's got the accent... and the outfit ...and the name...
Voiced By: Nikki Rapp (Tales of Monkey Island)
Morgan LeFlay is a pirate bounty hunter and huge Guybrush Threepwood fangirl hired by the Marquis De Singe to track down Guybrush and retrieve his Poxed hand. She does, happy with the chance to meet her hero, and returns the hand to De Singe. De Singe then sends Morgan to bring back the rest of Guybrush, but when she tracks him down they are swallowed by a giant manatee. The two escape by working together, and Morgan reluctantly brings Guybrush back to De Singe.Feeling bad about selling Guybrush out, Morgan tries to get Guybrush's Poxed hand back to him. LeChuck kills her before she gets the chance. In the Crossroads Guybrush has to convince Morgan that she did not waste her life. She in turn helps Guybrush defeat LeChuck again. The post-credits stinger shows Morgan giving the Voodoo Lady LeChuck's remains in exchange for letting her return to the land of the living as a ghost.
Died in YourHook HandTonight: Sadly, Morgan does this in Guybrush's arms (on a starry night, no less) after telling him about the incident in De Singe's "laboratorium". Poor Morgan and Guybrush.
Disposable Fiancé: In Chapter 3, we learn from the Assassin's Ledger and the tattoo on her arm that she once had a first love named Gustavo (or "Gus" as her tattoo calls him), but once she became Pirate Hunter, she probably had no use for him and... let's say... disposed of him, even though her Pirate Hunter's Code was not to "kill someone [she wasn't] getting paid to", and Gustavo was her exception.
Hello, Nurse!: Even Murray, who is nothing more than a disembodied skull, tries to hit on her.
I Call Her "Vera"/The X of Y: According to the Assassin's Ledger and De Cava, she purchased a ship for 10,000 pieces of silver, the same price that was paid to her for killing Prince Hipolito de Toro, and called it "The Knave of Toro" after her exact same victim! Creepy!
Also, the sword that she has is called the Blade of Dragotta, simply because it has the name of her mentor, Dante Dragotta, written on it!
Tsundere: Starts off aggressive, though upbeat, becomes nicer the longer she spends time with Guybrush.
Coronado De Cava
Voiced By: Andrew Chaikin, a.k.a. Kid Beyond (Tales of Monkey Island)
Coronado De Cava is the ex-boyfriend of the Voodoo Lady, who went in search of La Esponja Grande in order to impress her. During his search for the sponge, De Cava and his crew were swallowed by a giant manatee. Already an unstable man, De Cava went insane trying to escape from the manatee.When Guybrush and Morgan LeFlay meet up with De Cava, both of them pretend to be a couple so De Cava does not think Guybrush is in a relationship with the Voodoo Lady and kill him. Guybrush, Morgan, De Cava, and his crew escape from the manatee, but when he sees that Guybrush has La Esponja Grande and is convinced that Guybrush's relationship is a fake (unaware that Guybrush had manipulated the Voodoo Lady's locket), he attacks Guybrush's ship. Luckily the manatee re-swallows De Cava and his entire ship.
A Father to His Crew: De Cava lampshades this in Chapter 3 when he tells Guybrush and Morgan about his crew members (Bugeye, Moose, Santino and Noogie), "I may have been a stern leader, but I loved them like sons."
Talking to Himself: We hear De Cava speak with Bugeye in Chapter 3, and both characters are voiced by Chaikin, who also provides the voices for Joaquin D'Oro (Chapter 4), Murkel Trenchfoot, McGillicutty and two of his crew members of the Spoon Isle Trio.
Yandere: He really loves the Voodoo Lady, and is more than willing to kill anyone who stands between them.
Reginald Van Winslow is the captain of the Screaming Narwhal (which he had seized by knocking off the previous captain while losing his Club 41 "probationary membership" card in the process) until Guybrush wins the ship by knocking Winslow off of it. Afterwards Winslow stays on as Guybrush's first mate throughout the rest of the game, and in the end hooks up with the gender-ambiguous merperson Anemone.Notable for being the only crewmember Guybrush has ever had that fully got along with him and never mutinied.Winslow also heavily fetishizes maps and people pointing at maps, including Guybrush.Winslow also appears in Poker Night at the Inventory. He introduces the player to the Inventory, and runs the poker games.
Ambiguously Gay: Both in his attention to Guybrush, and in a far more literal sense in that the person he ends up with is of indeterminate gender, making whether he is gay truly ambiguous, even to him!
Defeat Means Friendship: Knocking Winslow off the Screaming Narwhal is how Guybrush gets him as a reliable first mate.
Large Ham: Like everyone else when they get really Poxed.
Talking to Himself: Besides Winslow, his voice actor Roger Jackson provides the voices of Hemlock McGee, one unnamed bartender of Club 41, and Galeb in Tales; the troll, one of the Pirate Leaders, Fred (the Man of Low Moral Fiber) and his rat, Jojo Sr., Spiffy the Dog, the Piranha Poodles and Meathook's parrot in the Special Edition of Secret; and Bart, Governor Phatt, the rat (again) and Toothrot's parrot in the Special Edition of Revenge. Neither of them have talked with each other, though.
Ozzie Mandrill is a ruthless Australian businessman who spends all of the fourth game attempting to gain control of the entire Caribbean, be it through simply buying up property, hostile takeovers, or political manuevers (or secretly committing crimes).
Big Bad: In Escape. LeChuck is still present, but he acts as Ozzie's dragon.
Bond Villain Stupidity: Subverted. He realizes that keeping Guybrush alive could hurt his plans, but he's too eager to have a hostage. So, he instead opts to maroon him on Monkey Island where he won't foil Ozzie's plans, but can still be used as a hostage if worst comes to worst. This apparently-smarter move ends up biting him in the end, though, but more through sheer bad luck than any ineptitude on Ozzie's part.
Butt Monkey: When he tries to make a bank transaction, but not really anywhere else in the game unless you count him being crushed to death by LeChuck's One-Winged Angel form.
Hopeless Boss Fight: You can challenge him to Insult Swordfighting, but it's impossible to respond to his ridiculously Australian insults in anything other than confusion. Luckily for Guybrush, the only thing Ozzie does if he wins is kick Guybrush out of his house.
Jerkass: And not in a funny way either. He's just a mean-spirited, unpleasant person.
Large Ham: Though he really doesn't start showing it until Guybrush learns that he's in cahoots with LeChuck.
Nice Job Fixing It, Villain: If he'd waited one more second before using the Ultimate Insult on LeChuck, Guybrush would've been killed before he had a chance to activate his own Ultimate Insult. He might have still been defeated by Horatio and Jojo, but he would have at least succeeded in killing Guybrush. Because of his actions, he didn't even accomplish that.
The Straight Man: Although Escape is a pretty wacky entry in the series, he is an almost entirely serious, humorless character even before you realize that he's the new main villain. Some critics, expecting an actually-funny antagonist, complained about this aspect back when the game was first released.
One particularly subtle demonstration of this trope is that he's the only character to avert the game's Running Gag of calling Elaine "Mrs. Marley" instead of "Mrs. Threepwood".
"What in the name of Adam Smith's Invisible Hand is that?"
"What the didgery-doo was that?!"
Xanatos Speed Chess: Within minutes after his original plan to kill all pirates, a plan that he spent years on, fails, he improvises and begins carrying out a new one, and he might have succeeded if Guybrush, Horatio, and Jojo hadn't stopped him.