Gilbert created LucasArts' 1987 adventure game Maniac Mansion, which set the stage for point-and-click graphic adventures to come and featured nonlinear gameplay mechanics uncommon in the genre to this day. In 1990 and 1991 respectively, LucasArts released The Secret of Monkey Island and Monkey Island 2: LeChuck's Revenge, created by Gilbert with co-writers Tim Schafer and Dave Grossman; the games have become Gilbert's strongest legacy. The designer then left LucasArts to found Humongous Entertainment, where he created several successful children's franchises and, at sister company Cavedog Entertainment, served as producer on Chris Taylor's celebrated strategy game Total Annihilation.

In recent years, Gilbert has maintained his blog and kept a relatively low profile in the games industry, working with various developers as a consultant. "I have been a fan of Penny Arcade because I have always found their comic so funny and biting," he said. "When I first heard they were making a game and that they had chosen to weave adventure game elements into it, I knew immediately I wanted to be involved. Working with the Penny Arcade guys and the team at Hothead has been an absolute riot."

"I can hardly believe it," said Penny Arcade writer Jerry "Tycho" Holkins. "The whole thing is super crazy."

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