The game was inspired by Gilbert's interest in pirates. In particular, the Pirates of the Caribbean theme park ride at Disneyland inspired him to create an explorable world populated by swashbuckling pirates.
A notable contributor was Orson Scott Card, acclaimed author of "Ender's Game", who wrote the insults for the "insult swordfighting" section.
The game contains a few references to the LucasArts game Loom. The SCUMM Bar contains a character from LOOM, wearing a pirate hat and a button reading "Ask me about LOOM". If asked, he describes the game with much enthusiasm.
The game pokes fun at the gaming conventions of game over. Though it is usually not possible to die in The Secret of Monkey Island, Guybrush can at a point in the game fall off a tall mountain. This prompts a dialog box proclaiming, "Oh, no! You've really screwed up this time! Guess you'll have to start over! Hope you saved the game!" and offering the choices "Restore, Restart, or Quit". This is similar to the death scenes of rival company Sierra Entertainment's adventure games of the time; seconds later, however, Guybrush bounces back into view and lands safely on the path. He offers the concise explanation, "Rubber tree.", and the game continues as normal.