Of all the decisions that have led Martin to this particular moment—the time he decided to drop out of NYU law school to become a comedian, even though he’d never done stand-up before; or the time he was flying home from L.A. after finding out NBC had canned his sitcom; or the time he attended his father’s funeral and realized, at age 20, just how short life is and how easily it can all disappear—perhaps the most significant was the time he decided to teach himself to write with his left hand. “I looked at my hands and thought, Why is it so hard to write with my nondominant hand?” he says. “What am I taking for granted in my regular dominant hand?” So for two months, he decided to write only lefty. This is the kind of challenge he habitually, almost compulsively, creates for himself. “His whole life is meticulous,” says his friend John Oliver of The Daily Show. “That’s his means of getting through the day. He lives his life like some kind of Greek mathematical genius. But try ordering with him in a diner.”
Writing left-handed, of course, made it much harder for Martin to jot down ideas for jokes. He decided to make this a game. He’d try to write each joke in as few words as possible. “I’d be like, This joke has twelve words. That’s so cool. This joke has seventeen words. That’s okay. But this joke has 22 words. That seemed like a concession.”
He sometimes likes to think of these short jokes as fractals, an idea he came across while reading James Gleick’s Chaos. “I thought, this is so interesting, this concept of self-similarity—how, if you have infinite resolution, you can see a pattern in a system repeating itself again and again.” In other words, he figured that if you can compose a successful six-word joke, you can build a six-minute set. And if you build a successful six-minute set, you can build a 60-minute act. And with a 60-minute act, you can conquer the world—or, at least, the nerd-hearted portion of the world that’s likely to respond to a comedian who’s prone to thinking of his jokes as fractals.
I first saw Martin perform live at the Zipper Theater back in 2005, and I remember having two reactions: Wow, this guy is really funny, followed shortly by Wow, what the hell is anyone ever going to do with him? His jewel-cut punch lines and homemade pie charts didn’t seem obviously transferable to, say, a buddy-stoner comedy. He readily acknowledges his two most apparent influences: the laconic one-liner kingpin Stephen Wright and Gary Larson, creator of the “Far Side” cartoons. And when he started doing stand-up in 1997, he was often warned his energy was too low and his jokes were too cerebral. He recalls, “I couldn’t believe it was a liability to be cerebral. I couldn’t believe that was going to be my Achilles’ heel.” His career thus far has been marked by smart people identifying his talent yet never quite finding the right way to showcase it. He spent a year writing for Conan, where his favorite segment to work on was “Actual Items,” because he could go off alone, flip through magazines, and let his mind wander. He later did a half-dozen “Trendspotting” segments for The Daily Show, in which he parodied youth-trend reporting, but his bits, while funny, seemed at odds with the mock-gravitas bombast of the show. “Sometimes Jon [Stewart] would say, ‘You’ve got good jokes in here, but it’s just too atmospheric,’ ” Martin says. “ ‘It needs to be more relevant.’ And I am typically not that relevant as a performer. Political stuff is not a good fit for me. I like to daydream.”
Not long after I saw Martin at the Zipper, I heard that NBC had given him a deal to write a sitcom, which seemed like a hilariously unlikely union. It was hard to imagine him hanging out in a café with a gang of four wacky friends, or living next door to a hot single mom with an adorable kid. Sure enough, the sitcom he wrote, called Williamsburg, about a George Plimpton–style participatory journalist, didn’t get produced.
It was the second time he’d tried to write a sitcom—the first was in 2001, after he did a “New Faces” show at Montreal’s Just for Laughs festival, at a time when networks were still trawling for the next Jerry Seinfeld or Ray Romano, and a crisp six minutes could land you a six-figure development deal. “People would do these sets that were like, ‘My mom is such a character! And my neighbor … ’ so the executives in the audience could say, ‘Yes, we can see your show. It’s your mom, and your neighbor, and you,’ ” he recalls now. “But my set was just one-liners.” Even so, the one-liners were funny, and Martin, with his camera-friendly looks and relatable slacker vibe, seemed like comedic clay that could be molded into a TV star. So he flew to L.A. and wrote a pilot with two veteran sitcom writers, in which he winds up living next to a single mom with an adorable kid. It didn’t get picked up.