One day, late in the summer of 2012, Spencer Crittenden drove to Meltdown Comics in L.A. to watch a taping of a podcast. Out of something between intuition and clairvoyance, he’d boned up on his lapsed hobby, Dungeons & Dragons, just in case it came up at the show. This tiny decision ended up radically altering the path of his life.

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Spencer Crittenden Part of being a dungeon master involves figuring out multiple outcomes for each situation, the hypothetical diverging paths each player might end up on with every roll of the 20-sided die. Even if he’d gotten especially creative with plotting possibilities for the night he went to see Harmontown live, though, Crittenden probably wouldn’t have anticipated it would lead to him join the podcast, become Dan Harmon’s assistant, and eventually develop a TV show with him. The cherub-faced, double billy goat-bearded performer grew up playing D&D, almost always in the role of dungeon master. He’d drifted away from the game in college, though, and by the time he started listening to Harmontown–the loose, live-wire podcast from the creator of Community–he hadn’t played in over a year. He was also in a weird place, having just gone through a breakup, and feeling trapped in his head most of the time while working at the Apple Store. When he realized the podcast hosted live tapings within driving distance, he worked up the enthusiasm to go to the next one. “I’m really antisocial,” Crittenden says. “I had been to one concert in my life at that point. I very rarely do anything. But Dan Harmon had mentioned D&D on the show before, and he’d also talked about how after the show they’d go to the bar and talk to people, and I thought I could maybe talk to them about Dungeons & Dragons like human beings.” He didn’t even have to wait until after the show. Toward the end of the fifth episode of Harmontown, Dan Harmon asked if anyone in the crowd has ever been a dungeon master before. Crittenden raised his hand immediately, and went onstage to field questions. Eventually, he agreed to generate first-level characters for Harmon and cohost (aka comptroller) Jeff Davis and come back for the following episode. He also ended up going out for drinks with the crew that night and learning about their plans for D&D on the show. Embarking on the “HarmonQuest” “Their idea was this kind of reality show thing, like The Bachelor, where they’d try out different dungeon masters and see who the next dungeon master would be,” Crittenden says. “But apparently they didn’t pursue that after the first night. That sounds like bragging. This is the part where I’m bragging, I guess.”

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If Crittenden’s first time on the show was an audition, he rendered the competition moot. Gradually, he became a dryly sarcastic fixture on the show, coming out onstage before the episode-ending D&D sessions to contribute commentary to rollicking discussions. A self-described “awkward mess” with no performing experience, he felt comfortable onstage because he was there to contribute with a skill set he’d been practicing over half his life. Fans of the show latched onto him, perhaps out of identification. He was one of them. Dan Harmon The following January, Dan Harmon took his show on the road, thus completing the fired Community showrunner’s transition into post-Tonight Show Conan O’Brien. Crittenden came along for the ride. The entire experience is documented in the film Harmontown, which is partially a time-lapse recording of Crittenden coming out of his shell. Right after the tour, though, Harmon’s experience stopped mirroring Conan O’Brien’s: He was hired back to Community for the show’s fifth season. Crittenden’s friends who took note of this new development began whispering that he might be able to get a job out of it. They were right. In a timely coincidence, he emailed Harmon about potential job openings just as the rehired showrunner was in the midst of losing an assistant. Crittenden soon officially came on board to fill the role. Aside from scoring a cameo in an episode of Community, the new job also brought the perk of more opportunities to think creatively. At first he just kept quiet and tried not to be in anyone’s way within the bustling office. After he learned that speaking up within the writers room wouldn’t necessarily get him yelled at, though, he started to occasionally suggest ideas. When the writers were stuck, he pitched possibilities that helped lead to a breakthrough. In the sixth season, he even got a couple of concepts onscreen (the use of a Ukrainian Teen Center as a random location, for instance.) Being around these writers at work also lit up the dungeon master part of his brain. “The thing about breaking a story is there’s billions of version of any one story, and you always have to hold in your head four or five parallel versions as you’re working through which one solves this problem or whatever, which is exactly like dungeon mastering,” he says. “You make a three-way fork in the road and you have to consider: Are they gonna take a left? The middle? The right? Are they gonna run away and bomb the planet? There’s all sorts of different ways that players can go, so you take a parallel version that didn’t work and you find one that might work and try to apply the differences.” Mastering a New Type of Dungeon Master-ing Meanwhile, the way that Crittenden played D&D onstage had begun to evolve. Typically, the game is played in marathonic bursts of four or five hours. On Harmontown, it went for more like 15-30 minutes. It was a whole new ballgame from what he was used to, mainly because most D&D players aren’t prone to thwarting their dungeon master at every turn for the purposes of comedy. If a character in regular D&D changes gears, the DM might have to write four new hours’ worth of plans. Crittenden had to learn to be as adaptable as the unpredictable show he was on. Whatever he was doing, though, it was working. This segment of Harmontown was so popular that when Dan Harmon bumped into an executive at NBC Universal and offhandedly pitched a web series spin-off, he was taken seriously. Harmon had a vision of playing D&D in front of a live audience, and interspersing it with animation so viewers could actually see the fantasy world. The network ran with the idea and funded an initial taping of six episodes. Eventually, when Seeso was developed under the NBC banner, the comedy network bought the show and ordered 10 new episodes.

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“I was on board right away, but I was in denial for years until it became time to really make the show happen,” Crittenden says. “So I became really involved once it all started.” Related: Cocktails & Chromatic Orbs: Keeping “Dungeons & Dragons” Vibrant for 42 Years Dungeons & Dragons director Nathan Stewart explains how he’s growing an old brand by sticking to its storytelling roots. With Harmon’s attention divided between writing a book, making the Adult Swim show Rick and Morty, and half a dozen other projects, Crittenden had some more freedom to push things forward with Harmonquest. He wrote the story depicted in the game roughly the same way he did with typical D&D, but putting more of a focus on plot arcs and big turns. The networks gave him notes on the story, but mostly it was limited to some minor tweaks. Finally, Crittenden was combining his storytelling instincts as a dungeon master with writing for TV. After all the live Harmonquest tapings were finished, the players sitting at a table in the middle of a dark stage, it was time to figure out the animation part of the equation. Crittenden and the team selected an art director who gave the characters a storybook image resembling old school D&D manuals for kids. The team also decided these characters should resemble Harmon, Davis, cohost Erin McGathy, and each week’s guest, to amp up verisimilitude. The resulting show is a joyful celebration of what can happen when you get funny people together to play D&D and none of them take the game or themselves too seriously. Writing a New Future Now that the show is wrapped, Crittenden is thinking about the future. He’d like a second season of Harmonquest, obviously, but he’d also like to write someday. “I have ideas for various scripts but I don’t think I’m quite there yet,” he says. “I wouldn’t want to show them to anyone.” The years of working as Harmon’s assistant haven’t just had perks like regularly appearing on Harmon’s History Channel show, Great Minds, it’s also given him some incredible training for life as a creator. He’s had access to all manner of insider meetings, he knows the nuts and bolts of making a show run, and he’s even learned how to make jokes work better in the editing bay. Now he just has to synthesize his new knowledge with the right idea.

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There are billions of possibilities for how attending that first podcast could have gone. Perhaps the way it was meant to go, though, is the way it went.