Monkey Island is one of the most beloved adventure game series ever made, a pirate comedy created by Ron Gilbert at LucasArts that has charmed players since 1990. Following the misadventures of wannabe pirate Guybrush Threepwood across the Caribbean, the series became the gold standard for point-and-click adventures thanks to its razor-sharp writing, inventive puzzles, and a sense of humor nobody has ever quite matched. Across six games and three decades, Monkey Island has weathered the near death of its entire genre and come out the other side with its reputation not just intact but legendary.
The humor in LucasArts games is always great, but the humor in the Monkey Island series is on another level. My first time playing I kept stupidly laughing at all the pirate insults.
The series follows a clear order, even if its history is a little tangled. It began with The Secret of Monkey Island in 1990, followed by Monkey Island 2: LeChuck’s Revenge in 1991, the two games Ron Gilbert originally helmed. The Curse of Monkey Island arrived in 1997 with gorgeous hand-drawn animation, and Escape from Monkey Island in 2000 moved the series into 3D. After a long gap, Telltale Games revived it with the episodic Tales of Monkey Island in 2009. Then in 2022, Ron Gilbert returned to bring the saga full circle with Return to Monkey Island, a direct follow-up to his original two games.
At the center of every game is Guybrush Threepwood, a hapless, lovable doofus who arrives in the Caribbean declaring “I want to be a pirate” and stumbles his way into heroism. His foil is the ghostly, zombie, and at times demonic pirate LeChuck, an undead villain endlessly scheming to win the heart of Governor Elaine Marley, who happens to be the love of Guybrush’s life. The supporting cast is just as memorable, from Murray the wisecracking demonic talking skull to the mysterious Voodoo Lady and the impossibly slick salesman Stan. Dominic Armato has voiced Guybrush since The Curse of Monkey Island, and his performance is so definitive that the character is hard to imagine any other way.
What truly sets Monkey Island apart is its comedy. The games are genuinely, consistently funny in a way few titles ever achieve, built on clever wordplay, absurd situations, and puzzle solutions that reward lateral thinking without ever feeling unfair. The most famous invention is insult swordfighting, where duels are won not with skill at arms but by trading better insults, with the immortal exchange “How appropriate, you fight like a cow” becoming a series signature. Running gags like grog, the three-headed monkey, and Guybrush’s ability to hold his breath for exactly ten minutes have become beloved touchstones for fans. This is humor writing at the highest level the medium has produced.
For decades, fans assumed Ron Gilbert would never return to the series he created, especially after the rights changed hands. That changed in 2022 with Return to Monkey Island, developed by Gilbert’s studio Terrible Toybox alongside Devolver Digital and Lucasfilm Games. Co-written with longtime collaborator Dave Grossman, the game serves as a direct sequel to 1991’s LeChuck’s Revenge, effectively picking up the thread Gilbert left dangling thirty years earlier. Its modern, stylized art direction by Rex Crowle drew some initial criticism from fans expecting pixels, but the finished game won over players and critics alike with the wit and heart that defined the originals. Dominic Armato returned as Guybrush, and for many longtime fans it felt like the proper ending the series always deserved.
The series has been preserved and updated over the years, most notably through The Secret of Monkey Island: Special Edition in 2009 and a similar remaster of LeChuck’s Revenge in 2010, both of which added new art and full voice acting while letting players toggle back to the classic look. The rights to Monkey Island now sit with Disney through its ownership of Lucasfilm, the same path that runs through the rest of the LucasArts catalog. The series stands shoulder to shoulder with the other LucasArts adventure greats, and its influence runs through nearly every comedic adventure game made since, including the work that came out of studios like Telltale, which also handled the Sam and Max games. Few series have aged this gracefully, and the central mystery hinted at in the title still keeps fans theorizing to this day.
Monkey Island endures because it was never really about pirates or puzzles. It was about making players laugh and think in equal measure, and it did both better than almost anything before or since. Whether revisiting the originals or jumping in with Return to Monkey Island, the series remains a high-water mark for what adventure games can be.