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.
Each of the games takes place on fictional islands in the Caribbean around the Golden Age of Piracy sometime between the 17th and 18th centuries. The islands teem with pirates dressed in outfits that seem to come from films and comic books rather than history, and there are many deliberate anachronisms and references to modern-day popular culture.
The main setting of the Monkey Island games is the "Tri-Island Area", a fictional archipelago in the Caribbean. Since the first game in the series, The Secret of Monkey Island, three of the games have visited the eponymous island of Monkey Island, while all have introduced their own set of islands to explore. Monkey Island 2: LeChuck's Revenge features four new islands, but does not return to Monkey Island until the final cutscene. The Curse of Monkey Island introduces three, and Escape from Monkey Island, which revisits some of the older islands, features three new islands as well. As such, the "Tri-Island area" actually comprises a total of 13 visitable islands. Tales of Monkey Island takes place in a new area of the Caribbean called the "Gulf of Melange".
The main islands of the Tri-Island Area are Mêlée Island, Booty Island, and Plunder Island governed by Elaine Marley in place of her long lost grandfather, Horatio Torquemada Marley. Elaine moves from island to island at her convenience, though she considers her governor's mansion on Mêlée Island, the capital island of the area, as home.
Other islands in the region are considered under the umbrella of Tri-Island Area as well, even though not directly governed by Elaine include: Lucre Island, Jambalaya Island, Scabb Island, Phatt Island, Hook Island, Skull Island, Knuttin Atoll, Blood Island, Spittle Island and Pinchpenny Island.
The Gulf of Melange has its own set of islands: Flotsam Island, the Jerkbait Islands (Spinner Cay, Spoon Island, Roe Island), Brillig Island, Boulder Beach, Isle of Ewe, and the Rock of Gelato.
Monkey Island and Dinky Island are not officially part of any island area, but nonetheless are central to the series' overall back-story and canon.
The games have a wide cast of characters, many of which reappear throughout the series. Each entry in the series revolves around three main characters: the hero Guybrush Threepwood; his love interest Elaine Marley; and the villain, the ghost pirate LeChuck. Several other characters such as the Voodoo Lady, Stan the salesman, Murray the Demonic Talking Skull and Herman Toothrot make multiple appearances within the series as well.
Ron Gilbert's two main inspirations for the story were Disneyland's Pirates of the Caribbean ride and Tim Powers' book On Stranger Tides. The book was the inspiration for the story and characters, while the ride was the inspiration for the ambiance. "[The POTC Ride] keeps you moving through the adventure," Gilbert said in an interview, "but I've always wished I could get off and wander around, learn more about the characters, and find a way onto those pirate ships. So with The Secret of Monkey Island(TM) I wanted to create a game that had the same flavor, but where you could step off the boat and enter that whole storybook world."
Several specific references to the ride are made throughout the series, including a puzzle in the second game based on the ride's famous Jail Cell/Dog With Keys scene (the dog in the scene is even named Walt). The banjo music in the opening menu of the third game is also very reminiscent of the banjo music at the beginning of the ride. Additional references are made to Disneyland and theme parks in general throughout the series, including Guybrush finding an E ticket.