Punk-Rock Comedy in a Late-Night Suit

In praise of David Letterman, the preeminent establishment-backed comedy revolutionary, on the day of his final show.

Jason Diamond is the author of Searching for John Hughes (HarperCollins/William Morrow). His next book, The Sprawl, will be published by Coffee House...

I got into David Letterman young—like, way younger than one should get into a guy whose show didn’t go on until past midnight. But I’ve always been a bad sleeper, so as a little kid, after a few hours of lying awake, I’d walk into the family room, turn on the television, and pass out to whatever was on. That time of night in the mid-’80s, there weren’t many options.

I still remember my first time: 1986, a Late Night episode featuring Chris Elliott playing an exaggerated and pompous version of himself—smoking a cigar, making a cappuccino, wearing a puffy blue track jacket that made him look like a flashback-version of some low-level member of Tony Soprano’s crew. Letterman played along, acting the part of the straight man as best he could, but something about the scene, this irreverence or anarchism I was still at least a decade away from being able to define, informed kindergarten-age me that, as real as it seemed, what I was watching was a joke. Even if I didn’t know why it was funny, I understood that it was great.

Meanwhile, in Los Angeles, a few years before Letterman would banter from behind his desk with his bandleader Paul Shaffer, the musician Peter Ivers—possibly better known as the songwriter behind “In Heaven,” the eerie tune sung by the Lady in the Radiator from David Lynch’s Eraserhead—somewhat bombastically proclaimed that his own show, New Wave Theatre, offered a glimpse into “the direction television and film will [hopefully] take in the ’80s." Watching videos on YouTube today, Ivers might not look like a contemporary of Letterman's, with his weird suits and rambling, political monologues, but he wasn't far off. Featuring a number of Los Angeles punk bands, including Fear, the Angry Samoans, and the pre-45 Grave, post-Bags death-rock band Castration Squad, New Wave Theatre was a precursor to MTV, but also featured strange sketches and comedy bits that were probably more influenced by Dada than Saturday Night Live. Too avant-garde for any big network, looking more like a post-punk version of TV Party, the show was initially broadcast on an independent television station, KSCI Los Angeles. The format differed from Letterman’s early days, but there seemed to exist a kinship nonetheless.

If there was anybody trying to push new or weird artists from his small slice of late-night television, it was Letterman. Whether it was giving R.E.M. their television debut in 1983, or probably confusing plenty of viewers by interviewing Captain Beefheart more than once, it has always seemed as if Letterman felt more excited to be talking to the underdogs and the freaks than the biggest celebrities in the world. You saw it in his genuine excitement, last March, over a performance by the band Future Islands, which he followed by yelling, “I’ll take all of that ya got!” Just over a year later, Letterman had the indie band on a second time. There are Oscar winners who weren’t invited to appear on the show so frequently.

Still, despite his relative risk-taking, Letterman’s show wasn't TV Party or New Wave Theatre—shows you couldn’t imagine following Carson or surviving in any network television time slot. He isn’t a cult comedian; he’s been watched by millions of people since the early 1980s. But his sense of humor was and is strange, stranger than many of his peers in any era, strange enough that his ascent to mainstream stardom would be unlikely today, never mind decades ago. He would repeat jokes over and over even if nobody laughed, and looked more like Alfred E. Neuman than a TV idol. He even had his own brand of pre-Internet viral content, spread by people asking their friends if they’d seen his Stupid Pet Tricks or Top Ten Lists. But he was still on late at night, and when people caught him before his tenure in CBS’s 11:35 slot, it was likely at least a little serendipitous.

The first time Gethard saw Letterman, he tells me, he was camping in Cape May, New Jersey, in a small trailer with his whole family, when a brutal storm hit. “And afterwards,” he says, “I guess my mom had a lot of adrenaline and couldn't go to sleep, because I woke up in the middle of the night and she was dying laughing watching Letterman on this little black and white TV we kept in that trailer. I don't think I've ever seen her laugh that hard.”

There’s a Leonard Cohen quote I like about how “the last refuge of the insomniac is a sense of superiority to the sleeping world.” For a long time, late-night comedy was for the weirdos, the stoners, the insomniacs, and whoever else was up when the rest of the world had gone to bed. Watching a show like Letterman’s when he was on NBC made you feel less alone—as if there were other people out there like you, too. Today, with the ability to watch the best things from the night before on the web, the dynamic is different. Conan O'Brien and Craig Ferguson, when their shows aired after Leno and Letterman, occupying the same time slot Letterman once had, were maybe the last of the truly great late-night weirdos. O’Brien hasn’t lost it, but, after proving too unpredictable during a short stint in the Tonight Show seat, had to head into the uncharted waters of TBS for a shot at another show; Ferguson, passed over for Letterman’s briefly vacant chair, walked away. And all due respect to modern masters of the form such as Jimmy Fallon and Jimmy Kimmel, but it feels counterintuitive to measure the success of comedy anarchy in YouTube views, impossible as it seems to imagine those shows going gloriously off the rails as anything other than an engineered bit.

“I didn’t know if the stupid stuff would alienate people,” Letterman said in a recent New York Times interview with Dave Itzkoff. “I didn’t know if the traditional stuff would be more appealing. And then, when I look back on it now, of course the answer is, you want to do the weird thing.” And the weird thing, ultimately, was what made Letterman who he’s been for the last three decades: a rarity who did pretty much what he wanted, and was paid handsomely for it—the establishment-backed comedy revolutionary whose brilliance warped countless impressionable minds while the rest of the world slept.

Jason Diamond is the author of Searching for John Hughes (HarperCollins/William Morrow). His next book, The Sprawl, will be published by Coffee House Press in 2020. His work has been published by The New York Times, New York Times Magazine, The Paris Review, Esquire, Rolling Stone, The New Republic and many other outlets.