The game begins on an island in the Caribbean. The main character by the hilarious name of Guybrush Threepwood who’s goal in life is to become a pirate. There is a ghost pirate named LeChuck that is madly in love with the Governor of Melee Island, Elaine. During the course of the game, he kidnaps Elaine and takes her to Monkey Island. Guybrush gathers a crew, buys a boat and sails to Monkey Island to rescue Elaine.

The game is an adventure game. Pretty much you have a cursor that you can click on things. You can look, use, take, etc. many items. Those items can in turn be used in other places to either open more of the story or get you more items.

The game is full of jokes and references to other games and movies. One of the best known jokes is the “Stump Joke” where the player finds a stump in the forest maze on Melee Island. When you look at the stump, Guybrush looks inside and says he can see an opening inside it with catacombs. He then tries to go inside and at this point the game says insert disk #22 to continue. Since the game originally came on 4 or 8 diskettes, there is no disk #22. You hit enter and it keeps asking for higher and higher numbered disks until Guybrush finally gives up and says, “I guess I can’t go down there. I’ll just have to skip that part of the game”. That joke caused so many people to call Lucasarts and complain or ask for the missing disks. It was then removed from the re-releases of the game.

The game is so popular it has a cult following online. When they were going to release Tales of Monkey Island, a 5 part game for the Wii, PC, Xbox 360 and the Playstation 3, they decided to re-release the original game. The 2009 re-release had updated graphics and sound and featured full voice acting by the voice actors from the other games in the series. Unfortunately, the Stump Joke is missing.