Production began in early 2009; franchise creator Ron Gilbert was involved in project planning, while development was led by Dave Grossman, who co-designed the first two Monkey Island games.

Critics praised the game's story, writing, humor, voice acting and characterization; 1UP.com described Guybrush as Telltale's strongest and most expressive character yet.

A sixth entry in the franchise, Return to Monkey Island by publisher Devolver Digital, Lucasfilm Games and Terrible Toybox, was released on September 19, 2022.

Before the game's beginning, Guybrush spends years locating the elements needed to create the Cursed Cutlass of Kaflu, a voodoo weapon capable of destroying his nemesis, the demon pirate LeChuck (Adam Harrington,[23] Kevin Blackton and later Earl Boen).

[24] As with other Monkey Island games, LeChuck vies for the love of Elaine Marley-Threepwood (Alexandra Boyd),[22] the wife of Guybrush Threepwood and former governor of the Tri-Island Area.

Other additions to the cast include Coronado DeCava (Andrew Chaikin), an explorer and former lover of the Voodoo Lady, and the Marquis de Singe (Jared Emerson-Johnson), an antagonistic French nobleman and doctor.

[25][27] Having acquired the components of the Cutlass of Kaflu, Guybrush races to the Rock of Gelato to save his wife from LeChuck; however, he fails to properly create the sword.

Escape from Monkey Island and Sam & Max Hit the Road co-designer Michael Stemmle contributed design and story writing, in collaboration with Mark Darin and Sean Vanaman.

[52] On his blog, Gilbert wrote that he was "very excited" for both Telltale's adaptation and LucasArts' reimagining of the original game, and stated that "it's strange and humbling to see something you created 20 years ago take on a life of its own".

The final artwork, showing Guybrush and Elaine brandishing cutlasses on a ship emerging from fog, was favored as Purcell felt it was appropriately eerie.

[59][60] Xbox Live was omitted from the initial release, as both Telltale's Wallace & Gromit's Grand Adventures, and LucasArts' special edition of The Secret of Monkey Island, were debuting on the system.

[22] Grossman maintained that both the story and gameplay of Tales of Monkey Island were designed to be accessible for newcomers to the series, and commented that "knowledge of the characters and their history will add a nostalgic layer to the sly references, but is by no means necessary".

By the game's third episode, Telltale became unsatisfied with this system, and began diversifying facial features, and providing supporting characters with unique silhouettes and animations.

[22] Grossman explained that both Telltale's art department and game engine are oriented toward 3D graphics development, and that the company enjoys the benefits 3D offers in the areas of animation and cinematography.

[61] Improved capacity for the latter resulted in the appointment of a "cinematic director": someone to help the designers locate scenes needing more dramatic activity, and to assist the animators and choreographers in creating it.

This was remedied by changing the time of day from dusk to night, adding rain and other weather effects, and using camera movement to simulate rough waters.

Telltale believed that this control method made for a less passive and more engaging player experience, and provided more freedom for cinematic camera work than was possible with point-and-click.

[72] In-house Telltale composer Jared Emerson-Johnson said that his own role in the game's music was "technical and administrative",[27] and that, while he had been willing to assist Land, "the sound of the Monkey Island universe is all about Mike’s vision, so he was left alone to 'do his thing' as only he can".

[70][72] Armato enjoyed his opportunity to voice Guybrush again; he had believed that the series would never be continued, due to the length of time since Escape from Monkey Island's release.

[75] To make the actors' portrayals more forceful, Telltale implemented a lip sync system capable of presenting a large range of facial expressions on character models.

Presented as a cartoon version of Tales of Monkey Island, the shorts speculated on the game's story and content, and depicted hypothetical events for the upcoming chapters.

[80] For the final installment, released on December 4, Fietzek recruited Smudo of the German hip hop band Die Fantastischen Vier to do a musical number.

[27] A week after the release of the first episode, Telltale held a contest called "Game Designer for a Day", which gave fans the opportunity to submit and vote for a line of dialog to be used as an accusation against Guybrush.

[116][118][124] Critics considered "Lair of the Leviathan" to be stronger than the previous chapters; on the review aggregator sites GameRankings and Metacritic, its Windows version holds the highest rating out of all Tales of Monkey Island episodes.

[128][130] Dickens described the chapter's story as "strong [and] advancing",[126] and Ghiggino felt that it "continued the fine Monkey Island tradition of being bizarre, hilarious and pretty interesting".

[134][136] Reaction to the chapter's plot was mostly positive, with Eduardo Reboucas of Game Revolution commenting that it "moves along at a steady pace, and ends with a dramatic bang".

[137] Several reviews praised the twists in the story,[133][136][138] although Adventure Classic Gaming's Mark Newheiser opined that the darker turn late in the episode was detrimental to the otherwise light-hearted series.

[144] Nevertheless, the story received strong praise,[142][143][145][148] particularly for the role reversal between Guybrush and LeChuck;[141][146] Destructoid's Anthony Burch noted that the chapter "completely and intentionally inverts [Monkey Island's] own cliches".

[146] Similarly, the writing and dialogue were commended,[144][147][149] as was the voice acting,[145][147] with critics praising Earl Boen's reprisal of the demon LeChuck and Armato's work as Guybrush.

[141][142] Reviewers complimented the graphics for both the ghostly "Crossroads" and the fire-ravaged real world;[141][145][148] Butts expressed that "the levels all benefit from great color choices and fantastic lighting effects that really support the mood".