Before his professional career started, Ron Gilbert didn't think he'd be making video games for a living. But when an interest in filmmaking transitioned into a love of programming, a plucky upstart developer named Lucasfilm Games would soon enter Gilbert's life and dramatically change his trajectory.

That was 30 years ago, and, in the passing decades, Gilbert's more than made a name for himself in the video game industry. While he started at Lucasfilm Games as a humble programmer of Commodore 64 ports, it would only be a few years before Gilbert spearheaded some of the most beloved entries in the point-and-click adventure game genre: Maniac Mansion and The Secret of Monkey Island. And when his Lucas-branded employer found itself in what many would call its Golden Age of Adventure Games, Gilbert made a bold move by leaving to form Humongous Entertainment, a brand that undoubtedly holds a lot of nostalgia for people currently hovering around their mid-20s. Just as Guybrush Threepwood and Purple Tentacle evoke certain memories to people of my generation, characters like Putt-Putt, Pajama Sam, and Freddi Fish are just as special to those a little bit younger.

Ron Gilbert. (Image courtesy of Adventure Gamers.)

After more than a decade of making games for the younger set, Gilbert returned to the sphere of gaming we're more familiar with, consulting on Penny-Arcade Adventures and Tales of Monkey Island, and designing the action-RPG series, DeathSpank. But it's only been in recent years that Gilbert's returned to his true calling: adventure games. 2013 saw The Cave, a Double Fine-published project that adapts classic adventure game mechanics into something more akin to a side-scroller. And if The Cave represented a step towards Gilbert's reunion with adventure games, his upcoming project, Thimbleweed Park, amounts to a zero-gravity leap. Even in its early stages, this upcoming, crowdfunded adventure game—which also features the work of Maniac Mansion artist and collaborator Gary Winnick—is already living up to the promise posted on its Kickstarter page: "It’s like opening a dusty old desk drawer and finding an undiscovered LucasArts adventure game you’ve never played before."

Though Gilbert is currently knee-deep in development, he recently set aside some time to speak with me for the purpose of a full retrospective on his long career. And if you notice that we steer slightly away from his most famous creations, Maniac Mansion and Monkey Island, there's a good reason for that. Since he's already discussed these subjects at great length publicly—including with me—I decided to instead concentrate on some of the lesser-explored avenues of his time within the games industry. What follows is a discussion that spans decades of gaming history—one that may reveal things you never knew about this storied creator.