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Spitting the sand of Monkey Island from my mouth, I began to wonder if the life of a mighty pirate was all it was cracked up to be. If only I'd chosen a different path, LeChuck might still be dead, and the mystery of the Ultimate Insult might have remained an enigma. If I'd never picked up a sword, the grog-swilling pirates of the Tri-Island Area might be unthreatened by the twin forces of gentrification and demonic heckfire. If only...
—Excerpted from The Memoirs of Guybrush Threepwood: The Monkey Island Years

Escape From Monkey Island is the fourth game in the Monkey Island series, released in 2000. It was also the first 3D game of the series (which used a modified version of the engine from Grim Fandango). Guybrush and Elaine return from their honeymoon to find two problems: Elaine has been gone so long she's been declared legally dead, and is thus no longer governor of the Tri-Island area, forcing her to run for re-election against the challenger "Charles L. Charles". Furthermore, a sinister Australian businessman named Ozzie Mandrill has been buying up property all around the Caribbean, driving out the indigenous pirate-themed businesses (and the pirates along with them) in favor of coffee houses, theme restaurants, and other tourist traps. Guybrush soon discovers Mandrill is not only in league with a yet-again-resurrected LeChuck, but the two are after a sinister artifact known as the "Ultimate Insult" that will allow them to rule the Caribbean.

Tropes used in Escape from Monkey Island include:
  • Batman Cold Open: The game begins with a battle against nondescript pirates, in which the player must learn to utilize Guybrush's unique adventuring skills.
  • Bond Villain Stupidity: LeChuck does manage to realize that not killing Guybrush when he had the chance comes back to bite him.
  • Bound and Gagged: Guybrush and Elaine.
  • Chekhov's Boomerang: This is vital here, where you have a "meet yourself" scenario twice on your way to a particular destination, and the second time you have to repeat the exact sequence of events you experienced the first time. It doesn't help that the potential sequence of events is completely random, so there's no "one guide fits all" answer for solving the puzzle.
    • The banana picker.
  • Chewbacca Defense: Ozzie's Australian insults are so incomprehensible no one can counter them, so he always wins his matches.
  • Comedy as a Weapon: The results of the insult-themed sports are based entirely on insults and puns.
  • Corrupt Corporate Executive: Ozzie Mandrill.
  • Development Gag: In-game, the SCUMM Bar is replaced by the Lua Bar after a hostile takeover, named after the language used in coding the game.
  • Did Not Do the Research: Fargo is not the capital of North Dakota.
  • Easter Egg: Murrayball!
  • Explosive Leash: The Voodoo Anklet of Extreme Discomfort.
  • Expy: Pegnose Pete is very similar to Largo La Grande from Monkey Island 2.
  • Fan Service Pack: Guybrush is MUCH easier on the eyes in this game than in the last one.
  • God Test: Guybrush asks his future counterpart to guess what number he's thinking of.
  • Guide Dang It: The final round of Monkey Kombat turns into a Hopeless Boss Fight (for both sides) unless you get very lucky or you start fighting to draw.
  • Hijacked by LeChuck: Narrowly averted. LeChuck returns, but he's working for the new villain, and Demon Zombie Ghost Pirate Statue even gets taken control of when trying to double-cross him at the end
  • Hold Up Your Score: The cliff-diving judges in Escape.
  • Humongous Mecha: The monkey head from The Secret of Monkey Island is retconned into being part of a giant monkey robot which Guybrush powers up and uses to save the day.
  • Luck-Based Mission: The "Monkey Kombat" sequences near the end of the game are reliant on you either happening to start in a combat stance that beats your opponent, or the opponent being dumb enough to switch into a stance that is weaker than yours. What actually tends to happen is that the opponent immediately switches into whatever position beats yours, and stays like that for the rest of the fight. You basically have to get beaten 10--15 times and just pray to god that you learn enough stance switching commands to start getting somewhere; otherwise the game's effectively Unwinnable.
    • Not quite unwinnable. You can learn most of the moves without much tedium, and as with Insult Sword Fighting in the previous games, you don't have to know all of them to win.
  • The Maiden Name Debate: A lot of people, especially natives of Melee Island, assume that Guybrush has become Mr. Marley.
  • The Man Behind the Man: In a rather surprising plot twist, Ozzie is the real Big Bad of this game while LeChuck is just The Dragon.
  • Melee a Trois: In the climax of Escape, it's Guybrush vs. LeChuck vs. Ozzie. Though this translates to you facing LeChuck.
  • My Grandma Can Do Better Than You: The Insult Arm-Wrestling features this potential exchange:

 "My ninety-eight-year-old grandmother has bigger arms than you."

"Ungh... Yeah, but we both got better bladder control than you do."

  • No Flow in CGI: Probably the reason why Guybrush has such a tiny, pathetic ponytail in this one.
    • On the other hand, Elaine's hair is bigger than ever, but noticeably stiff.
  • No Fourth Wall: Used extensively.
  • Nostalgia Level: Major sections of the game take place back on Melee Island and Monkey Island, complete with similar geography and reunions with characters/objects from the first game (Carla, Otis, Meathook, the stuck clock tower, the banana picker). Unfortunately, the nostalgia appeal seems to have failed.)
  • One-Winged Angel: LeChuck in his Giant Statue Form.
  • The Other Darrin: Once played by the very British Alexandra Boyd, Elaine is now played by the very American Charity James.
  • Paper-Thin Disguise: Ignatius Cheese is the only one who wasn't surprised at Charles L. Charles's real identity.
  • Shapeshifting: LeChuck does this one here, switching between his ghost, zombie and demon forms as well as Charles L. Charles.
    • He already showed this capability in the first game, disguising himself as a sheriff named Fester Shinetop.
  • Shout-Out: The name "Ozzy Mandrill" brings to mind a certain poem by Shelley. Furthermore, Mandrill says something to the effect of "Look upon my works, ye pirates, and despair." It also sounds like the name of the Star Wars character Ody Mandrell.
  • Stable Time Loop: The Mists o'Tyme Marsh sequence has a part there the player will meet a version of himself from the future, exchange some dialogue and swap inventory items. The player has to remember and duplicate this sequence exactly for when they revisit the same place as their future self.
  • Stealth Pun: Guybrush hires a navigator named Ignatius Cheese. The short form of Ignatius is Nacho.
  • Symbol Swearing: In Act III, Guybrush asks Herman Toothrot, "How do I get off this [bleep] island?", as the swearing is bleeped in the dialogue and replaced by symbols in the in-game text.
  • Talking to Himself: Dominic Armato ("What kind of weird duck are you?")
  • Title Drop: Very blatantly: Whenever the title is dropped by Guybrush, it's spoken in a bombastic movie trailer voice.
  • Tradesnark: "Nice use of the ™."
  • Unholy Nuke: The Ultimate Insult is one of the most powerful Voodoo artifacts around; it's not that lethal for the body, but annihilates the spirit.
  • The Un-Reveal: When Guybrush asks the Voodoo Lady's name.

 Voodoo Lady: My name is... not important.

  • Villain with Good Publicity: Charles L. Charles, LeChuck's alter ego, who wins the election for governorship of the Tri-Island Area with his "Good Times, Free Grog" policy.
    • This drops to Zero-Percent Approval Rating after he wins and everyone realizes he's LeChuck, although no-one will actually admit to having voted for him.
  • Weaksauce Weakness: Pegnose Pete is terrified of ducks.