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"Three small trials and you're a pirate like us." Fair enough. If only I could stomach the foul brew these scurvy seadogs swilled, the rest would be easy. How could I have known I'd meet a powerful and beautiful woman with a jealous suitor too stupid to realize he'd been dead for years? And how can I crawl through this great stone monkey to find a man who walks three inches above the ground and sets fire to his beard every morning?
— Excerpted from The Memoirs of Guybrush Threepwood: The Monkey Island Years
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The first game in the Monkey Island series, The Secret of Monkey Island, was released in 1990. The game begins as our hero, Guybrush Threepwood, finds himself on Mêlée Island, with one clear objective on his mind: Becoming a Mighty Pirate™. To become one, he must first pass "The Three Trials", and while doing so he learns of Elaine Marley, the local governor, and her story with the notorious ghost pirate, LeChuck, who now terrorizes the waters around Mêlée Island™ together with his undead crew. After passing the trials, Guybrush finds out Elaine has been kidnapped by LeChuck, and he must now set sail for LeChuck's lair which lies on the titular Monkey Island™ in order to save her.

Way later in 2009, LucasArts got back in the Adventure Game business (finally redeeming themselves in the eyes of adventure fans) by remaking the game, complete with voice acting by the cast of The Curse of Monkey Island.

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This game provides examples of:

  • Aerith and Bob:
    • Guybrush Threepwood and... almost everyone else. Although you do get the occasional LeChuck, Herman Toothrot, or Mancomb Seepgood.
    • The Amazing, Adventurous, Acrobatic And Exceedingly Well-Known Fabulous, Flying Fettucini Brothers are called Alfredo... and Bill.
  • All Just a Dream: The game's littered with clues that this might be the case, as was Gilbert's original intention. They've mostly been Retconned into either Medium Awareness or Anachronism Stew. While this has never been explicitly Jossed, Gilbert has claimed that "it was all just a dream" is NOT the elusive Secret, and that the ending of the second game was always meant as a joke and a cliffhanger.
  • Always Night: It's always 10 p.m. on Mêlée Island, even as hours pass. Can't be a good sign.
  • And Now You Must Marry Me: Elaine Marley is not a smart person to try this on.
  • And Your Reward Is Clothes: Twice:
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    • "I found the Legendary Lost Treasure of Mêlée Island™ and all I got was this stupid T-shirt!"
    • "I beat the Sword Master and all I got was this stupid T-shirt."
  • Anti Poopsocking: These parting words: "Turn off your computer and go to sleep."
  • Art Shift:
    • Most conversations between Guybrush and another character will feature a close-up shot of that character in a highly detailed and realistic portrait. It is this realism that clashes with the visual style of every other game. The original EGA release had the close-ups in a style somewhat more consistent with the rest of the game's graphics — compare Elaine's EGA close-up with its VGA counterpart — and Ron Gilbert objected strongly to the more detailed style that was added in the later VGA release, but was overruled by the higher-ups at Lucasarts.
    • The redrawn artwork in the remake - the shift is so drastic that there is actually a petition to have Guybrush's hair changed back to how it used to be and a fan-made patch restores the good old ways.
  • Aside Glance: Guybrush frequently turns to the player when voicing his descriptions out loud, but seems confused when other characters do the same.
  • Audience? What Audience?: Herman Toothrot keeps turning to the screen and talking to "the people watching, of course." Guybrush asks him who he's talking to (even though he's constantly doing the same thing himself).
  • Barefoot Sage: The Voodoo Lady's long dress doesn't cover her bare feet.
  • Bilingual Bonus: If you understand French, you might more easily guess the purpose of the "caniche endormi" (literally, "sleeping poodle") flowers.
  • Bland-Name Product:
    • The 'Grog-O-Mint' mints Guybrush buys to give to Otis are this of Lifesavers Pep-O-Mints, or Polo mints to UK players.
    • The Grog machine is a Coca-Cola vending machine, red with a white stripe, just with "Grog" in place of "Coke".
  • Bloody Bowels of Hell: The catacombs (implied to be part of the capital "H" Hell) have eyes, noses, whole faces, and even hearts growing out of the walls and floors. Crosses over with Fire and Brimstone Hell, due to the rivers of magma. If you spend too long wandering through The Maze, looking at every random horror, Guybrush starts to think they're "Neat!" and "Gnarly!" He never gets used to the mushrooms, though.
  • Book-Ends: The conversation in the outro cinematic is similar to the one that begins the game.
  • Boring Return Journey: Getting to Monkey Island takes up an entire chapter (and that's after you've obtained the ship and the crew); getting back again is over in a single line of narration. Lampshaded by Guybrush.
  • Buffy Speak: "...and the Trial of, err, Treasure Hunter-y."
  • Bread, Eggs, Milk, Squick:
  • Breaking the Fourth Wall:
    • After receiving sword-fighting lessons from Captain Smirk, Guybrush says, "I can’t help but feel like I’ve been ripped off," then turns towards the screen and continues, "I’m sure you're feeling something similar." On the other hand...
    • If you look at Monkey Island™ from your ship Guybrush will say, "WOW! This was well worth $59.95 plus tax."
    • One of the dialogue options the player can make when challenging a pirate to a fight is to ask "Why do you guys talk so funny?" to which the pirate will reply (breaking accent in the Special Edition), "Pirate Lingo! It's how everybody talked back then. Come on Guybrush, play along."
    • Monkey Island castaway/hermit Herman Toothrot occasionally addresses comments to the fourth wall. At one point, Guybrush asks who he's talking to, and he replies, "The people watching, of course!" — to which Guybrush reacts as if he's crazy, even though, as these examples show, he does the same thing.
    • In Monkey Island's river canyon area, the player can move the cursor over the sun and urge Guybrush to walk to it. He then turns towards the screen and says "Oh, sure. Walk to the sun."
  • Brick Joke: If you dissolved the top half of one of LeChuck's ghostly crew with root beer during the final act, his legs go running past Guybrush and Elaine during the ending.
  • Bring the Anchor Along: The Trial of Thievery ends with Fester Shinetop tying the stolen item, the Idol of Many Hands, to Guybrush Threepwood and dropping him in the bay. How does our hero get out of this? Just pick up the Idol. You know, the one he was just carrying a few seconds ago. It should be noted this is the only part of the game in which Guybrush can actually die.
  • Cannibal Clan: The Monkey Island cannibals. They're very civil. Their leader doesn't even really seem to want to eat you. In Curse, Lemonhead reveals they went vegetarian shortly after Guybrush left the island.
  • Cannot Talk to Women: When Guybrush first meets Elaine, he is unable to do anything except utter random syllables. In their second meeting he acquits himself better, but the conversation quickly turns to increasingly saccharine pet names, which in a way is worse. He relapses into gibberish in later games whenever a woman is upset with him, indicating Guybrush just cannot take a woman's scorn.
  • Cardboard Prison: The cannibals imprison Guybrush in one. He escapes thanks to a loose board. As a running gag, the clueless captors throw Guybrush in jail again and upgrade the door several times up to modern technology levels if Guybrush comes back.
  • Cave Mouth: The giant monkey head statue opens up to the Caverns of Meat that lie between you and LeChuck's ship.
  • Chekhov's Gun:
    • Conspicuously, you can walk inside the big church in the middle of Mêlée Island™ Town, but it serves no purpose until the final act.
    • Same goes for the vending machine at Stan's.
  • Comedy as a Weapon: The results of sword fights are based entirely on insults and puns.
  • Confusing Multiple Negatives: Guybrush can promise LeChuck's ghostly first mate he "won't not promise to avoid refraining from harming you" (which, once translated, means you don't promise not to hurt him). It doesn't work — it's too confusing for him to understand, so you have to really promise in order to continue.
  • Convenient Misfire: In the church scene, when Guybrush tries to christen LeChuck with root beer, the bottle jams.
  • Conveniently Placed Sharp Thing: Parodied through inversion in the underwater sequence. LeChuck ties a heavy statue to Guybrush's leg by rope, and throws him into the ocean. He is dragged down to the ocean floor, only to find that it is practically littered with sharp objects with which he might cut the rope — except they are all just out of reach.
  • Copy Protection: The "Dial-a-Pirate" code wheel. The game would start off with a "short quiz", and show a picture of a pirate (made from two halves of the heads on the code wheel) and asking when they were hung in a specific location. Once you rotated the wheel accordingly, the year for every possible location the game would ask would be revealed on the wheel, and typing in the correct answer would let you proceed. This was only present in the original EGA release and the slightly later VGA update. Beginning with the CD release, the copy protection was removed since it was still the early days of the CD-ROM format when copying one was unheard of.
  • Covers Always Lie: See Guybrush exploring Monkey Island, sabre in hand and leading a group? It's not going to happen. In the game he bumbles alone and unarmed.
  • Creator Cameo: The Troll Bridge that demands a troll toll is actually George Lucas in a troll costume. (This is made much clearer in the special edition, where you can even see a red plaid flannel shirt sticking out when the suit is unzipped.)
  • Crying Wolf: After Guybrush overuses his "Look Behind You! A three-headed monkey!" Catchphrase, the cannibals of Monkey Island™ don't fall for it when an actual three-headed monkey shows up behind them.
  • Cutting the Knot: The glorious underwater idol puzzle. Several sharp objects that could free Guybrush are just out of reach. If you wait long enough, two guys walk onto the pier, lengthily debate tossing a sword into the ocean directly over your head... then decide against it and walk off again. Then in a unique instance, Guybrush dies for real.
  • Damsel in Distress: In the second half the game you are supposed to save Elaine from getting married to LeChuck. But just as Guybrush interrupts the ceremony, he finds out Elaine had freed herself a long time ago, due to LeChuck's gullibility, and was just about to complete the final step in her plan for getting rid of him, and now he just messed it up.
  • Description Cut: In the ending, Guybrush wonders what happened to various characters. Cut to Stan plunging into the Mêlée Island™ bay several minutes after being Megaton Punched by LeChuck — then to Guybrush's crew imprisoned by the Monkey Island™ cannibals and blaming Guybrush for the rock he catapulted into their ship, or, if you didn't sink the ship, to Herman Toothrot, still stranded, still wondering where Guybrush is.
  • Deserted Island: The titular island, of the Castaway/Treasure Island variety.
  • Developers' Foresight:
    • For the Special Edition, they recorded Guybrush saying various amounts of money he might have. If your current total is not one of those recorded, he just says he has enough to buy anything he might need.
    • They also recorded two takes on each insult comeback — one that is said confidently when it's the correct comeback, and another that's said awkwardly when it's the wrong one.
    • If you try to steal from the shopkeeper by picking up an item and leaving the store, he'll remember it and continue to call you out for it whenever you talk to him. If he's not in the store and you try to steal from him, he'll return just in time and furiously call you out for trying to steal when he's not there.
    • If (and when) you drop the Swordmaster's insults on regular pirates, they automatically lose the round, but they call you out on it.
    • At one point, Guybrush boasts that he can hold his breath for 10 minutes. Much later in the game, you have to beat an (extremely easy) puzzle while underwater. If you wait the full ten minutes instead of solving it, which can only really happen intentionally, you die (the only real way to die in the entire game.)
  • Dirty Old Man: The shopkeeper is more than happy to go visit the Sword Master as many times as you need him to.
  • Do You Want to Haggle?: Guybrush starts off in a decent, if not great, bargaining position with Stan, about to buy a subpar, no-frills ship from him for a price that's almost his entire line of credit or more; the game then gives you options to either wheedle him down to less, or act like a cagey negotiator but naively keep raising the offered price so that Stan can take him for all 5000 pieces of eight. Whichever way you play it, it soon becomes clear that Guybrush was cheated — the ship's worth less than even his lowest possible bid.
  • Dummied Out: Played with: There's a certain stump in the woods of Mêlée Island™ with a tunnel hidden underneath it, leading into what Guybrush describes as a system of catacombs. However, it's impossible to enter it, as the game requests the player to insert several floppy disks that didn't come with the game, and Guybrush simply concludes that the catacombs are inaccessible. Many players didn't realize this was a joke, however, a fact which is referenced in the sequel (and its 2010 Special Edition).
  • Edible Theme Naming: The Fettucini Brothers, particularly Alfredo, a reference to the pasta dish.
  • Exact Words: Elaine rebuffs LeChuck and tells him to "drop dead". "And so he did." LeChuck's ghostification is not fully explained but a figurative meaning is also hinted and his eventual death might have occurred later during the trip to Monkey Island™.
  • Expressive Mask: The Monkey Island cannibals — Red Skull and Sharptooth wear huge masks with moving mouths. Lemonhead (also The Quiet One) just bobs his head up and down.
  • Fire and Brimstone Hell: The catacombs are implied to be part of Hell, and have pools and rivers of magma. Not to mention body parts growing on the walls and floors, see "Bloody Bowels of Hell" above.
  • Foreshadowing: In the Special Edition LeChuck and Sheriff Shinetop are both voiced by Earl Boen, though with different accents. When you talk to Otis in the first act, he leaves you with the words, "It's not like I'm the ONLY pirate on the island."
  • Fungus Humongous: The Caverns of Meat located beneath the giant monkey head have more than their share of spotted, hairy, waist-high toadstools. Guybrush hates them even more than all the bleeding giant organs jutting from the walls.
    Guybrush: Somehow I knew there'd be mushrooms in Hell.
  • Funny Background Event: During the ending, Guybrush wonders aloud what happened to Stan, which leads to a brief cutscene of him falling into the sea by the docks. If you allow LeChuck to Megaton Punch Guybrush back to the docks before using the root beer on him however, then Stan will fall into the water in the background while Guybrush and Elaine obliviously watch the fireworks created by the exploding LeChuck.
  • Gargle Blaster: Grog, which contains one or more of the following: kerosene, propylene glycerole, artificial sweeteners, sulphuric acid, rum, acetone, red dye #2, scumm, axle grease, battery acid, and/or pepperoni. It's so vile that it dissolves the mugs used to contain them, which leads into a puzzle where you have to carry a mug of grog from one location to another.
  • Gibberish of Love: Guybrush is reduced to gibberish when he first meets Elaine. He gets over it (barely) on their second meeting.
    Guybrush: Bgglw! Mfrnkf? Dmnkly... —sigh— I really wish I knew how to talk to women.
  • Have a Nice Death: Parodied, as this was the beginning of the trend of not being able to die in Lucasarts adventure games.
    • Parodied where Guybrush can fall from a cliff and a Sierra-style death screen appears for a moment — before Guybrush reappears thanks to a "rubber tree."
    • As you may repeatedly brag in dialogue options, Guybrush can hold his breath for ten minutes. Failing to solve the underwater idol puzzle during that time provides the game's only actual death. While there's no message or prompt to reload, after Guybrush drowns, the verb menu changes from Walk to, Look at, and so on, to Float, Bloat, Decompose, and to drive the point home, Buy Hint Book. You can watch the whole ten-minute ordeal (with music and a Sierra-style death message added by the uploader) here.
  • Hell Gate: The tunnels of Hell literally open up underneath Monkey Island. As a tourist attraction, no less.
  • Heroic Comedic Sociopath: Some mild examples compared to the sequel; Guybrush's crew getting stranded and captured by the cannibals is played for laughs and Guybrush can kill Bob with root beer when Bob outlives his usefulness, right after Guybrush promises him not to in exchange for information.
  • Hook Hand: Meathook, who lost both hands and an eye to a ferocious beast... a terrifying parrot. Not the same one he now keeps under lock and key on Hook Island (although he's just as afraid of that one). How it happened, we'll never know.
  • Hypocritical Humor: A pirate at the Scumm Bar laughs at Guybrush's name and calls it the stupidest name he's ever heard. When you ask for his name, though...
    Pirate: My name is Mancomb Seepgood.
  • I'm a Humanitarian: Subverted. The Monkey Island Cannibals have been trying to cut back on red meat for health reasons. According to the village nutritionist, they need to worry about their cholesterol.
  • Impersonating an Officer: In this case, Sheriff Fester Shinetop, a magically disguised LeChuck.
  • In Which a Trope Is Described: The naming conventions for each "part" of the game, setting the formula for the rest of the series.
    Part I: The Three Trials
    Part II: The Journey
    Part III: Under Monkey Island
    Part IV: Guybrush Kicks Butt
  • Island of Mystery: The titular Monkey Island and its eponymous secret... which we're never told. What the secret isn't, apparently, is the fact that you can't get there without some kind of magic, that it's inhabited by a tribe of cannibals, or that there's a literal gateway to Hell underneath.
  • It Belongs in a Museum: Guybrush can claim that the Idol of Many Hands "belongs in a museum" when Sheriff Fester Shinetop catches him trying to steal it. Note that in neither case Guybrush actually means it, and it's just one of the optional lines of dialog to try to get the item for himself. However, the owner of the idol does agree with that statement.
  • Jail Bake: Parodied with the carrot cake Otis apparently received from his Aunt Tillie. He doesn't even try to cut a slice himself because he hates carrot cake. Of course, Guybrush finds a use for the file hidden inside...
  • Just Like Making Love: "Swordfighting is kinda like making love. It's not what you do but what you say what's important."
  • Level Grinding: An unusual appearance of the trope in an adventure game. You must wander the island getting into insult fights to learn insults, then you must get into another fight in order to use the insult and learn the response.
  • Lost in Translation: Not as a bad as the infamous Monkey wrench, but the book "How to Get Ahead in Navigating" taken by the cannibals in exchange for their navigator's head also has its translation problems in other languages. Also, the idiom "Red Herring", whose meaning is necessary to know in order to advance, doesn't mean anything in other languages. Fortunately, it happens early enough on the game that you're bound to have very few items with you, and you already know you have to GIVE something, so at most you only have to try a few times.
  • Lost Woods: The Maze on Mélee Island™ is one, and both the treasure of Mélee Island™ and the Swordmaster are hidden in it.
  • Love at First Sight: Guybrush for Elaine. Also, if you decide not to save the idol task for last in The Three Trials, you get to see a scene that reveals that Elaine also fell for Guybrush at first sight.
  • The Maze: One in the woods of Mêlée Island™ and one in the Bloody Bowels of Hell beneath Monkey Island™.
  • Meanwhile, Back at the…: ...ghostly ship of LeChuck, anchored in a sea of lava...
    Deep beneath Monkey Island™
  • Megaton Punch: LeChuck repeatedly punches Guybrush straight up into the air above Mêlée™, sending him flying across the length and breadth of the island during the finale — an Astronomic Zoom displays Guybrush's ballistic trajectory. Stan gets socked into the bay as well.
  • Multiple Endings: Did you sink your own ship with the catapult? Your crew won't take it well... Watch. Escape from Monkey Island makes it the canonical ending; the crew resents Guybrush for abandoning them.
  • Nice Job Breaking It, Hero!: No Monkey Island would be complete without at least one instance:
    • A literal example when Guybrush sinks his own ship on Monkey Island™ with a catapult hit, but it has no gameplay consequences and only provides a slightly different ending, with your crew left stranded on Monkey Island. Watch.
    • Guybrush in the final act ends up being a Spanner in the Works to Elaine's plan, crashing the wedding just in time to stop her from zapping LeChuck herself.
  • No Animals Were Harmed: In addition to the prominent disclaimer stating that the developers do not in any way condone animal cruelty, Guybrush comments on the poisoned dogs: "They're only SLEEPING!!!"
  • Non Sequitur, *Thud*: "...I'm Bobbin, are you my mother?"
  • Noodle Implements: In the offscreen fight against Shinetop in the Governor's Mansion, Guybrush uses various random items for purposes unknown. He comes out of the fight with a Manual of Style, staple remover, and gopher repellent, of which only one is actually useful later in the game.
  • Offscreen Moment of Awesome:
    • The two sequences in which Guybrush tries to steal the idol in the first place. Much of the action takes place automatically in a room that you can't see; all you can see is dialogue and the actions that Guybrush is doing, many of which you can't normally do in the game. The highlight is perhaps "Hypnotize quarrelsome rhinoceros". The fight between Guybrush and the Sheriff in the Governor's Mansion starts out pretty funny and then keeps getting more and more insane.
    • Elaine escapes from an undead pirate, carries out a plan to kill said pirate... offscreen. Then comes Guybrush and...
  • Oracular Head: A severed navigator head which guides you through hell.
  • Or Are You Just Happy to See Me?: "Is that a banana in your pocket or are you just happy to see us?"
  • Pig Latin: When one of the Cannibals, Sharptooth, tells Guybrush that he can't go through the Caverns of Meat to get the Voodoo Antiroot without something, Red Skull (another cannibal) interrupts and tells Sharptooth, "Ixnay on the Eadhay of the Avigatornay!", but Guybrush has no clue what they're talking about (they're talking, of course, about the Head of the Navigator). It is lampshaded, of course:
    Guybrush: Why are you guys talking in Pig Latin?
    Red Skull: [to the other Cannibals] I see he is baffled by our native dialect. Good.
  • The Pirates Who Don't Do Anything: The pirates of Mêlée Island are too afraid of LeChuck to go raiding, so the spend most of the first act getting drunk. This ends once LeChuck has been and gone, they cheerfully loot the governor's mansion and leave now that there's nothing to be afraid of.
  • Player Cruelty Potential: After getting your hands on the root beer on Monkey Island, you have the opportunity to use it to destroy Bob. While he is apparently LeChuck's right-hand man, he also happens to be a Minion with an F in Evil who was Press-Ganged and murdered into undeath, so offing him can seem a little cruel.
  • Pragmatic Adaptation: While almost every single detail of the original is preserved in the Special Edition (and every detail is intact if you use the "original version" button), to sidestep the outrageous amount of voice acting it would require, rather than stating the exact number of Pieces of Eight that he has after getting paid by the Fettucini Brothers, Guybrush's description for his money becomes "I have enough money to buy whatever I need."
  • Pre-Asskicking One-Liner: Guybrush gets the option for a lot of these in the last act, aptly named "Guybrush Kicks Butt". Of course, you have the option to have him say something incredibly dorky and awkward instead.
  • Protagonist Without a Past: Guybrush's background prior to washing up on that beach in the first game is never elaborated on at all. Due to the serious plot contradictions, though, that became one of the fans' least concerns.
  • Public Domain Soundtrack: The SCUMM Bar music is a rendition of the old English drinking song "O Good Ale, Thou Art My Darling".
  • Psycho Poodle: The Governor's Mansion is protected by poodles that have been cross-bred with piranhas (somehow). Guybrush has to get past them by stewing meat with yellow flowers. (It Makes Sense in Context.)
  • Pun: The game needs you to recognize one to solve a puzzle. See Lost in Translation up there.
  • Red Herring: Subverted; the literal red herring you pick up in the game has an important use: it's the only item you can use to bribe the bridge troll.
  • Robinsonade: The Monkey Island arc. Guybrush and Herman Toothrot before him. With Go Mad from the Isolation elements, later subverted.
  • Saved by the Platform Below: If Guybrush gets too close to the edge of a particular cliff, it will break off and he'll fall, apparently to his death. a false Have a Nice Death message appears for a few seconds, then disappears as Guybrush soars back onto the plateau, with the explanation that he landed on a rubber tree (Needless to say, rubber trees do not work this way in real life).
  • Scooby-Dooby Doors: Most of the doors on Mêlée Island take you to a random other door in the town.
  • Seesaw Catapult: Herman Toothrot has built a fixture on Monkey Island that he insists is modern art, but consists of a log placed over a rock with a boulder on one end. This leads to a puzzle in which Guybrush must turn the log to the correct angle and drop a rock from an overhanging ledge in order to knock down a banana tree on a distant beach. If he gets the angle wrong, he may hit his own ship, resulting in slight embarrassment on his part and an extra scene in the ending in which his crew are marooned on the same island.
  • "Shaggy Dog" Story: Two of the final long quests are practically rendered moot; Elaine escapes the villain's clutches on her own, and you bungle her attempt to destroy the villain. The potion which can destroy ghosts is actually root beer, which can be found in the vending machine on the very island where the story began. In fact, Elaine's competence means that Guybrush's entire journey is technically moot, as she would have taken out LeChuck on her own had he not been involved.
  • Shout-Out:
    • Many to other LucasArts games, including Loom, the Indiana Jones series, and (in the Special Edition artwork) Day of the Tentacle and Grim Fandango. The Indiana Jones references (most notably "I'm selling these fine leather jackets") make more sense if you realise that Indiana Jones And The Last Crusade was the previous Lucasarts adventure game and introduced the more realistic graphical style and interface that Monkey Island used.
    • When you are about to crash the wedding between LeChuck and Elaine, you have a choice of dialogue for Guybrush, one of which being just shouting "Elaine!" In fact, that's actually a shout out to The Graduate. Word of God says that's where Elaine's name came from.
    • In a swordfight, one of the opening options is: "My name is Guybrush Threepwood. Prepare to die."
    • In the demo version of the game, Guybrush has the option to call one of the pirates in the SCUMM Bar a "kwyjibo."
    • Otis' name is an homage to Otis Campbell, the jailbird and drunk from The Andy Griffith Show, while Sheriff Fester Shinetop's first name is most likely an homage to the equally bald Uncle Fester.
    • The circus music has a part which sounds like the music typically used in circus settings, Entrance of the Gladiators by Julius Fučík.
    • Two of the idols surrounding the gigantic monkey head resemble Sam and Max, of Sam & Max: Freelance Police — Steve Purcell was one of Lucasarts' animators/background artists at the time. The Special Edition changes this to Purple Tentacle (you can tell by the angry monobrow) from Day of the Tentacle.
    • At one point, Guybrush can be made to walk off a cliff. The player is then shown a parody of Sierra's Have a Nice Death menus, before Guybrush bounces back into view and explains, "Rubber tree." Also a good-natured Take That!:
      "Oh no! You've really screwed up this time! Guess you'll have to start over! Hope you saved your game! <Restore, Restart, Quit>"
    • "That's the second-biggest monkey head I've ever seen!"
    • When Herman Toothrot sees the Sea Monkey, he calls Guybrush "braver than you look," a reference to how Princess Leia says "you're braver than I thought" when she sees the Millennium Falcon in Star Wars: A New Hope.
    • At the end of the special edition credits: "Guybrush will return. Guybrush will return."
  • Shrunken Head: At one point, Guybrush trades a book called How to Get Ahead in Navigating for the shrunken head of a navigator who helps him through a labyrinth.
  • Speak Now or Forever Hold Your Peace: Of course this is the moment when Guybrush interrupts the wedding.
  • Spoof Aesop: "At least I learned something from all of this..." Among the other possible options:
    Elaine: What's that?
    Guybrush: Never pay more than 20 bucks for a computer game.
    Elaine: (beat) A what?
    Guybrush: I don't know, I'm not sure why I said that.
    (Smash to Black, end credits roll)
  • Spy Speak: "Excuse me, do you have a cousin named Sven?" "No, but I once had a barber named Dominique." "Close enough." Guybrush wasn't making Dominique up, as the pirate barbers in The Curse of Monkey Island mention that he used to be the fourth member of their quartet.
  • Stalker with a Crush: LeChuck toward Elaine and the storekeeper toward Carla.
  • Stalking Mission: Guybrush chases the storekeeper to learn the location of the Sword Master. Knowing the path ahead of time isn't enough, since the shopkeeper knows the trick to revealing the final part of the path, but if you have the map, you can walk all the way on your own and use the sign on the ravine, just like the store keeper does.
  • Stop Poking Me!: There is a rat you can pester by hovering your mouse over him. Doing this repeatedly will cause it to run away, and a nearby group of pirates will get mad at you.
  • Sufficiently Advanced Bamboo Technology: Parodied. The cannibals of Monkey Island™ have state of the art security doors for no reason beyond the Rule of Funny.
  • That Was the Last Entry: The Captain's log found in the Sea Monkey. It ends abruptly when the two characters described in the log leave the ship to investigate the eponymous Monkey Island, leaving their fate a mystery. note 
  • Theory of Narrative Causality: Herman Toothrot has a ship that he can use to leave Monkey Island any time he likes, but he waits to be rescued because that's how things are done when you're a castaway on a tropical island. He even offers to loan his ship to Guybrush on the condition that he rescues him with it.
  • The Three Trials: Swordplay, thievery and treasure hunt-er-y. The Trope Namer.
  • Title Drop: Shown in the Captain's log, complete with the "TM" suffix.
  • Too Dumb to Live: Herman Toothrot has been waiting to be rescued from Monkey Island for decades, but has had a fully-functioning ship the entire time. Similarly, Otis has been waiting to be freed from jail for years, but has had a fully-functioning file the entire time—he just would rather eat rats than the carrot cake containing said file.
    • Also the ghost in the final part who loves root beer despite it killing him.
  • Took a Level in Badass: The final part, aptly named "Guybrush kicks butt", has GB gleefully one-hit-killing ghost pirates with root beer.
    • Guybrush learns how to fence and toss around insults like a pro.
  • Totem Pole Trench: With monkeys, in the wedding dress, as part of Elaine's cunning plan to defeat LeChuck that Guybrush inadvertently spoils.
  • Tradesnark™: Monkey and Mêlée islands always have "TM" on them.
  • Tragic Villain: LeChuck's crew were Press-Ganged and made ghosts by force, as his first mate recalls with bitter irony.
  • Troll Bridge: Although the scary bridgekeeping troll really is George Lucas in a suit.
  • Understatement: The corpse of Herman Toothrot's friend is labeled "unhealthy-looking man," but then again Toothrot said he looked even worse while he was alive...
  • Unexpectedly Realistic Gameplay: Sheriff Shinetop has you thrown off the pier tied to the golden idol you were tasked with stealing from the Governor's manor, leaving you to drown. How do you get out of this predicament when every tool that could cut the rope is just out of your reach? Just pick up the idol itself.
  • Updated Re-release: The Secret of Monkey Island: Special Edition, which doesn't just recreate the game — it is the game, with a new interface, graphics and voice acting built on top of the original SCUMM code. Before that, there was the CD-ROM version, which improved all of the audio, added new ambient tracks, and overhauled the HUD compared to the original floppy disk versions.
  • Villainous Crush: Evil pirate LeChuck had been love with Elaine for years. She told him to drop dead... so he did, sailing off in search of Monkey Island and getting himself killed along the way. Which actually made him an even worse scourge on the Caribbean than he was when he was alive.
  • Walk, Don't Swim: Guybrush, when tied to the idol and thrown off the pier, marches slowly around the sea bottom.
  • Weaksauce Weakness: Ghosts can be killed by dousing them with "voodoo anti-root" root beer.
  • Wedding Finale: The game's climax has LeChuck trying to forcibly wed Elaine and Guybrush crashing the wedding — except Elaine was already on top of things, so LeChuck was actually about to marry what turns out to be two monkeys in a wedding dress. Guybrush throws off her plans, and the now brideless LeChuck punches Guybrush straight up through the roof of the church.
  • Weird Moon: The Special Edition has an enormous moon hanging about in some of the backdrops. (Averted in the original version, where it's a much more reasonable size.) This is a nod to The Curse of Monkey Island, which likewise has several such moons visible throughout the game.
  • The X of Y: Various treasures and relics, such as The Idol of Many Hands you need to steal for the Trial of Thievery.
  • You Fight Like a Cow: The extended swordfighting subquest is the Trope Namer, with the original insults and their retorts written by Orson Scott Card.
  • Your Mom:
    • At one time if you let the Fettucini Flying Brothers argue over who gets to go in the cannon:
      Alfredo: Your mother wears combat slippers!
      Bill: Leave our mother out of it! Get in the cannon!
    • "So's your mother" is one of the options in Insult Swordfighting that won't win, although it only appears during the training scene with Captain Smirk.

 
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Guybrush meets Elaine

Wannabe pirate Guybrush Threepwood meets Governor Elaine Marley and gets severely tongue-tied.

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