The Monkey Island series is known for its humor and "player-friendly" qualities. The player cannot permanently place the game in an unwinnable state or cause Guybrush to die without great effort. This "player-friendly" approach was unusual at the time of the first game's release in 1990; prominent adventure-game rivals included Sierra On-Line and Infocom, both of which were known for games with sudden and frequent character deaths or "lock-outs". LucasArts itself used such closed plot paths for its drama games like Indiana Jones and the Last Crusade: The Graphic Adventure (1989), but preferred the open format for other humor-oriented adventure games such as Sam & Max Hit the Road (1993) and Day of the Tentacle (1993). After Monkey Island 2: LeChuck's Revenge in 1991, the series went in hiatus until 1997, when it resumed with The Curse of Monkey Island. After the fourth entry, Escape from Monkey Island, the franchise again went on hiatus, though numerous rumors persisted about a revival until the announcement of Tales of Monkey Island by Telltale Games in early 2009.

Much of the music of the games is composed by Michael Land. The score largely consists of reggae, Caribbean and dub-inspired music.

The series also tends to break the Fourth wall, as several of the characters acknowledge that they are in a video game.