Every Monkey Island Game Ranked: The Complete Guybrush Threepwood Legacy

Ranking every Monkey Island game has ended very poorly. What we didn’t expect was Joe to threaten to quit the group chat after Samuel said that Escape from Monkey Island wasn’t the worst thing he’s ever played. MARCUS attempted to play peacemaker while simultaneously defending Telltale’s episodic format, which only made Joe madder. Samuel wanted to assess each game’s puzzle design based solely on technical merit, as opposed to nostalgia. This caused yet another wave of bickering among the group regarding whether adventure game mechanics had advanced or deteriorated over the course of thirty years.

The argument really escalated once we tried to determine our criteria. Joe believed in evaluating the games strictly based on historical significance and pure design elegance. Samuel wanted to evaluate the games based on mechanical innovation and technical superiority. MARCUS kept going back to the narrative structure and the quality of the voice acting. No matter what we decided, none of us were able to agree on whether we should base our rankings on the games’ standards at the time of their release or how well they held up today. Ultimately, we decided to rank them based on puzzle design, storytelling ability, technical proficiency, and the overall impact the games had on adventure gaming — although we still fight about the ratio.

It’s the adventure game series that defines itself by Ron Gilbert’s original vision, and the legacy of the LucasArts point-and-click adventure game genre. The games defined what point-and-click adventure games could achieve when developers chose to emphasise creative puzzle designs, unforgettable characters, and actual humour over confusing logic and player frustration. From the original’s “no dying” philosophy to Return’s modernised accessibility, the series continually pushes the boundaries of what adventure gaming can do, while remaining true to its distinctively zany pirate comedy identity.

The Monkey Island series spans three decades of adventure game evolution. We’ve watched Guybrush transition from a low-resolution sprite to a fully-voiced character to a modern HD adventurer. We’ve watched the puzzle design philosophy shift, the methods of telling a story evolve, and the technology improve dramatically. Not all of the experiments worked, but every single game added something important to the history of adventure gaming.

Quick Rankings

1. Monkey Island 2: LeChuck’s Revenge | LucasArts – The perfect sequel that enhanced all aspects that were great about the first
2. The Secret of Monkey Island | Lucasfilm Games – The original template that demonstrated adventure games could be fun and intelligent
3. The Curse of Monkey Island | LucasArts – A beautiful hand-drawn animated film meets perfect voice acting
4. Return to Monkey Island | Terrible Toybox – Ron Gilbert’s triumphant conclusion to his unfinished story
5. Tales of Monkey Island | Telltale Games – An episodic revival that brought the spirit of the series to the modern era
6. Escape from Monkey Island | LucasArts – The 3D experiment that had incredible moments but lost the heart of the series

1. Monkey Island 2: LeChuck’s Revenge (1991)

Monkey Island 2: LeChuck’s Revenge was the point-and-click adventure game sequel that did everything right. Ron Gilbert and his team took the solid foundation provided by the original game and built upon it in all areas, preserving the delicate balance of challenge and accessibility that made the Monkey Island series unique. It is not simply a larger version of the first game; this is the full evolution of point-and-click adventure game design philosophy that will influence every point-and-click adventure game that follows.

Why it stands out: The multi-island layout that offered players true freedom to explore and solve puzzles across various islands. The inventory combination system that allowed players to experiment with items and combinations without punishing logical thought. The spitting contest on Phatt Island that may remain one of the most perfectly-designed mini-games in the history of adventure gaming. The graphical evolution that improved upon the original game’s already impressive visuals. The score by Michael Land that defined how adventure game music should complement the atmosphere without overpowering the dialogue. The final cutscene that completely flipped the script on player expectations and spawned decades of fan speculation and conspiracy theories.

Is it still relevant today? Yes. The puzzle design remains the pinnacle of logic-based puzzle design for point-and-click adventure games – difficult enough to offer a sense of accomplishment but fair enough that players will feel a sense of accomplishment for solving puzzles versus stumbling upon a solution. The writing is tighter than the original game; the pacing is better; and the technical advancements are so seamless that the series felt like a natural progression rather than a cash-in sequel.

Read Samuel’s in-depth review of why LeChuck’s Revenge set a precedent for point-and-click adventure game sequels →

2. The Secret of Monkey Island (1990)

The game that revolutionised the point-and-click adventure genre by demonstrating that challenging puzzles could be solved without player death, impossible scenarios, or ridiculous solutions. Ron Gilbert’s design philosophy of “the player should never become completely stuck” seems obvious today, however, in 1990, it was an entirely novel idea that separated Monkey Island from the Sierra adventure games that often punished players for even existing.

What makes it iconic: The insult sword fighting system that transformed combat into a battle of wits and established the concept that Monkey Island would always favour cleverness over brute force. The three trial structure that introduced new players to various ways of experiencing the game while introducing them to the organic learning curve of adventure game design. Guybrush Threepwood as a protagonist that was courageous, determined, and utterly inept in the most lovable manner possible. The dialogue system that allowed players to select the personality of Guybrush while providing a consistent narrative. Stan’s previously-owned vessel emporium, which remains one of gaming’s greatest comedy sequences. The SCUMM interface that made interacting with adventure games intuitive and less frustrating than guessing.

Is it still relevant today? The 1990 original shows its age visually, but the Special Edition demonstrates that the underlying design is timeless. The puzzles still function flawlessly; the humour has not aged; and the pacing is still top-notch. Modern players may find the pixel hunting occasionally tedious, but the core experience remains just as captivating today as it was thirty years ago.

Read Joe’s investigation into where point-and-click adventuring actually started →

3. The Curse of Monkey Island (1997)

The first Monkey Island game since Ron Gilbert departed that demonstrated the series could continue beyond its creator. Jonathan Ackley and Larry Ahern inherited a beloved property and somehow managed to take it in directions that felt both fresh and authentic to the original vision. The shift to hand-drawn animation could have spelled disaster, but instead produced the most visually stunning point-and-click adventure of the decade.

What makes it stand out: The cel-animated visual style that presented every screen as a piece of art worthy of the Golden Age of Disney while retaining the series’ unique visual identity. The voice performance of Dominic Armato as Guybrush that established how the character should sound and inspired every subsequent Monkey Island game. The Curse of the Ring storyline that cleverly inverted traditional adventure game concepts while continuing the series’ ongoing narrative. The expanded inventory system that made solving puzzles more complicated without becoming obtuse. Murray the demonic skull, whose presence elevated every scene with sheer comedic timing. The carnival sequence that showed how point-and-click adventure games could utilise set pieces to generate memorable dramatic scenes.

Is it still relevant today? The art style means that Curse of Monkey Island looks better today than most modern point-and-click adventure games. The voice acting established the benchmark that later games could barely meet. The puzzles occasionally tend toward moon logic, especially in the last sections of the game, but the overall experience remains enjoyable. While some of the references have aged, the essence of the adventure design philosophy and humour remains timeless.

Read MARCUS’s appreciation of beautifully drawn animation coupled with perfect voice acting →

4. Return to Monkey Island (2022)

Ron Gilbert’s return to Monkey Island after three decades demonstrated that sometimes you can go back home. This is not merely nostalgic baiting for middle-aged adventure game enthusiasts – it is a thoughtful assessment of what made the original games enjoyable, updated with modern design philosophies and a genuine respect for the player’s time. The art style initially split fans, but ultimately served the storytelling perfectly.

What makes it special: The multiple levels of difficulty that allow new players to experience the story without puzzle frustration while allowing veteran players to experience the level of challenge they desire. The meta-narrative elements that acknowledge the series’ complex history without being self-indulgent. Older, more reflective Guybrush as a character who retains his inherent personality while demonstrating genuine development. The puzzle design that replicates the logical-yet-brilliant puzzle design of the original games without seeming repetitive mechanically. The ending sequence that finally offers closure to Ron Gilbert’s original vision while opening doors for future storytelling. The modern accessibility options that ensure adventure gaming is inclusive without sacrificing design integrity.

Will it still hold up? It is a modern game, therefore the question is whether it justifies its existence. The answer is yes. Return feels like the natural next chapter in the series rather than a desperate cash-grab attempt. The puzzles work, the humour hits, and the story resolves long-standing questions that fans have debated for decades.

Read Joe’s analysis of how Ron Gilbert finally completed his story →

5. Tales of Monkey Island (2009)

When the commercial viability of adventure gaming died down, Telltale’s episodic reboot of Monkey Island came along and showed that the market still existed for clever puzzles and witty dialogue. Instead of being a gimmick, the monthly release schedule actually generated excitement as players speculated on plot twists and theories between each episode. This isn’t simply a strong Monkey Island game, it’s evidence that the series can be successfully adapted using modern storytelling tools.

What makes it untouchable: The episodic format where cliffhanger endings and continuous narrative storylines produced TV-style pacing in an adventure game. The cast returning in their previous roles from Curse and Dominic Armato’s Guybrush voice performance being the best since 1997. The DeSinge character being a compelling villain that utilised the series’ comedic side while generating fear in the player. The trial sequence, although subverting traditional adventure game conventions, provided character development for the player’s character. The conclusion of the game taking an authentic risk by emotionally investing the player in the fate of beloved characters. The use of modern input schemes to make adventure gaming accessible to a new generation of players who had never interacted with a SCUMM interface.

Does it still hold up? Although the episodic format has become less of a revolutionary concept since nearly every game is now using season pass models, the individual episodes of Tales of Monkey Island are well-designed adventure games. The graphics have aged far better than expected, the voice acting has consistently been exceptional, and the puzzle design has found a great balance between challenge and ease of playability. While some episodes of the series are stronger than others, the overall experience works.

Read MARCUS’s review of Telltale’s episodic return to Melee →

6. Escape from Monkey Island (2000)

This entry in the Monkey Island family attempted to modernise the series by utilising 3D graphics and contemporary adventure game design. Unfortunately, the experiment generally failed to deliver; however, Escape should be acknowledged for its attempts at creating an ambitious storyline and providing the occasional moment of true brilliance. While this is not a poorly designed adventure game, it is a moderately designed Monkey Island game, which is a key distinction.

Why is it interesting? The inclusion of satirical elements of politics that provided the series with relevance in modern times, while maintaining its timelessness as a pirate-based comedy. Ozzie Mandrill as a villain who embodied corporate cultural destruction and felt more relevant today than during the time he was created. The Monkey Kombat feature, which allowed players to divide themselves into camps, and represented a new evolution of the Monkey Island series puzzle design. The consistent level of quality within the voice acting, which remained high throughout the entire game despite the technical constraints of the time. Occasionally the art direction of the game captured the visual magic of the series, despite the limited 3D capabilities of the time. References to earlier games within Escape, that illustrated the series creators’ respect for continuity.

Does it still hold up? The 3D graphics of the game have aged significantly worse than Escape’s gameplay. The keyboard controls for Escape, and thus the gameplay, are clumsy when compared to modern standards, and some of the puzzles require a degree of frustration that exceeds the intended level of cleverness. Escape’s writing is inconsistent, and while it is sometimes brilliant, it is often dull and tedious. If you want to complete the series, then Escape is worth playing, but it does not represent the best that the Monkey Island series has to offer.

Read Samuel’s examination of the 3D experiment that caused the fanbase to split →

Almost Made the List

There was a lot of back-and-forth regarding whether to include the Special Editions of the original two Monkey Island games as individual entries. Joe argued that because they were such significant updates, they should be recognised individually, especially the addition of voice acting to the original scripts. Samuel argued that because they were essentially the same games with graphics upgrades, they did not deserve to dilute the rankings. MARCUS suggested that if they were to be included, it would set a dangerous precedent for how remasters compare to the original versions of games.

A large number of mobile adaptations were developed for the Monkey Island series. There are several versions available for different platforms with varying degrees of quality. Because of this, we collectively agreed to rank platform-specific versions of the game individually only if they offered significant amounts of additional content. For example, the iPhone version of the original game, while impressive for its time, is functionally identical to the original version of the game.

Secret of Monkey Island: Special Edition and Monkey Island 2: Special Edition both updated the classic Monkey Island games with improved graphics, full voice acting, and modernised interfaces. The option to switch between the classic and modern versions of the game at any time during gameplay was innovative, and the voice acting added to the original scripts was genuine. Nevertheless, these are the same games with technological advancements and do not constitute new creative works.

Several compilation versions of the Monkey Island series were released, including The Monkey Island Archives, which provided a convenient way to play multiple games in one place. These compilations did contain additional content, but none of it warranted individual rankings.

Additionally, we discussed whether Ron Gilbert’s early design documents and uncompleted projects should be included, but ultimately, we chose to focus on completed games.

Although the Monkey Island movie was cancelled, and a variety of tie-in merchandise was released, none of those items fall under the scope of this discussion.

In the end, we ranked every major release in the Monkey Island series that presented a complete adventure gaming experience. Mobile adaptations, special editions, and compilation releases helped preserve and promote the classic Monkey Island games, but the six games listed above represent the creative peak of one of the most influential franchises in adventure gaming history.

Debates will likely continue. Joe still believes that LeChuck’s Revenge is perfect in every way. Samuel will defend Escape more enthusiastically than it probably deserves. MARCUS will continue to argue that the addition of voice acting to the series changed it more than any other single element. But that is why the discussion surrounding Monkey Island is enjoyable after all these years.

Each of the games in the Monkey Island series has contributed to what adventure gaming could accomplish when game designers prioritise player experience over arbitrary difficulty. From the original game’s revolutionary accessibility to Return’s modern approach, the Monkey Island series has continually pushed the boundaries of the genre while retaining its distinct identity. Guybrush Threepwood remains one of the most endearing protagonists in gaming, and his continued adventures prove that the combination of clever writing and creative puzzle design will forever be in fashion.

Regardless of whether you are experiencing these games for the first time or replaying your childhood favourites, the Monkey Island series provides something rare in today’s gaming landscape: adventure games that respect the player’s intelligence while providing entertainment that will endure long after the initial experience has concluded. At a time when the gaming industry is often focused on graphics and action, the Monkey Island series reminds us that storytelling, character, and creative puzzle design create experiences that last decades. That is the real secret of Monkey Island.

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