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It’s Fun to Watch Old Clips of a Young David Letterman Figuring It Out

Launching a YouTube channel full of segments from his talk shows, the venerable comic puts his fascinatingly rough early years on display

For a couple generations of comedy fans, this week was all about David Letterman. The 74-year-old former talk-show host hasn’t been in the news much lately — the most recent season of his Netflix series My Next Guest Needs No Introduction aired back in the fall of 2020 — but he reemerged to celebrate the 40th anniversary of Late Night, the NBC show that made his name and gave the network a post-Tonight Show staple that thrives to this day. In fact, Late Night’s current host, Seth Meyers, had Letterman on the show Tuesday, a rare feat considering that Letterman prefers being out of the spotlight. 

But the other big event was an announcement that Letterman had launched a YouTube page that features, as a statement indicated, old clips from Late Night and Late Show (his subsequent CBS program) that are “artisanally-produced, carefully-curated and chosen completely at random by an old computer that used to pick numbers for the New York Lotto back in the ‘90s.” The timing seemed intentional: The clips started going live February 1st, 40 years to the day Letterman’s Late Night started airing.

Thus far, Letterman’s YouTube channel features several expected bangers: Letterman working the drive-thru at McDonald’s, Letterman having that supremely tense interview with Joaquin Phoenix, Stupid Pet Tricks. Those are all still pretty terrific, but they’re also the greatest hits — you’ve probably seen those dozens of times already. Instead, I highly recommend checking out some of the less-famous early clips that have found their way onto the page. Think of them as the deep album cuts that demonstrate just how original a late-night presence Letterman was even in those early days. But perhaps more importantly, they reveal a fascinatingly awkward, uncomfortable Letterman trying to figure out how to make this show work. 

Comedy nerds understandably tend toward the rapturous when discussing the original Late Night. As opposed to The Tonight Show, Johnny Carson’s venerable, cozy, show-biz-y L.A. show, Late Night was an ironic, willfully amateurish affair, almost as if Letterman was actively rejecting the chummy Hollywood-ness of his idol’s program. As Variety TV critic Daniel D’Addario put it recently about those early days, Letterman’s “sensibility was complicated (and, it should be noted, was by all accounts deeply informed by Letterman’s creative collaborator Merrill Markoe); it was giddily open to possibility, but nourished by a kind of sorrowful isolation. Letterman’s sense of the absurd came, it seemed, from his position at a remove from his guests, and from the audience.” There was a slight antagonism underlining Late Night, a sense that he wasn’t there to be our little dancing monkey. Everything from The Simpsons to Between Two Ferns bear traces of Letterman’s wiseass essence.

And while that’s all true, it would be inaccurate to say that Late Night emerged fully formed on February 1, 1982. Just watch some of the clips on Letterman’s channel for proof, especially the interviews. In the first few months of his show’s run, he talked to an irritable Paul Simon — “Do we have to go through the history?” the songwriter peevishly replies after Letterman asks him about starting a solo career after Simon & Garfunkel ended — and an intense Martin Scorsese, who hadn’t yet developed into the confident chat-show guest he’d eventually become. 

Those and other interviews — like Fred Rogers from February of that year, or the Gloria Steinem conversation that took place a few weeks later — are ultimately pretty interesting, but it’s almost in spite of Letterman. It’s not that he’s “at a remove from his guests” — it’s that he’s fumbling badly, clearly out of his depth. Plenty of talk-show hosts have to find their sea legs when they’re starting out — the early years of Conan O’Brien’s interviews were excruciating — but Letterman’s nerves are especially endearing because they contradict the surly, sarcastic persona we’ve come to associate with him. The Letterman in these clips is a guy who’d lost his previous program, a 1980 morning show called The David Letterman Show, after only about four months, the prospects of this one-time weatherman suddenly not looking particularly promising. You can sense that he knows that he’s got to make this show work.

But it’s not just Letterman’s discomfort that’s striking. Those initial Late Night episodes just generally feel weird, like a cable-access show that isn’t concerned that nobody’s watching at home. Guests come on with only applause, no music. The guests’ name occasionally appears on screen below their face when they’re talking, as if identifying a rare breed of exotic bird. And sometimes the audience doesn’t seem to know if they’re supposed to laugh or just listen. (The Fred Rogers clip is particularly surreal: Mr. Rogers is his usual eerily friendly self, and the crowd titters, not sure if this guy is for real. Is Fred Rogers exactly like that smiling wimp we saw on Mister Rogers’ Neighborhood?) 

That said, there’s something remarkable about that awkwardness: To watch these early clips is to be reminded of a talk-show universe before the entire format was transformed into a well-oiled machine. And I don’t just mean Late Night and Late Show — there’s none of the rehearsed-to-within-an-inch-of-its-life professional polish that all late-night shows now possess, which makes every celebrity appearance these days feel snappy but banal, all pre-planned and lifeless. 

By comparison, Late Night interviews meander in intriguing ways. And that tension allowed for some good moments, like when Simon admits that, after years of uninterrupted success, he didn’t know how to respond to people rejecting his then-recent film debut, 1980’s One-Trick Pony. Or there’s a 1983 interview with Magic Johnson where Letterman asks him about getting Lakers head coach Paul Westhead fired. The unscripted quality of these interviews is startling because they feel so different from the “Tell me about your exciting new movie” chitchat that happens now. If you want to see infamously contentious Late Night clips, such as the Jerry Lawler/Andy Kaufman faceoff, they’re on Letterman’s YouTube channel. But some of these lesser-known gems prove to be more revealing, an intimate glimpse of Letterman learning how to be a talk-show host.

In recent times, with his mighty beard and gentle air of gravitas, Letterman carries himself as an elder statesman, a symbol of a more refined age of television broadcasting. Sure, he made his living telling jokes and reading Top 10 lists, but remember how he brought the nation together after 9/11? And wasn’t he so much more dignified than that smarmy Jay Leno? On My Next Guest, he speaks to important figures, like Barack Obama and Kanye West and Malala Yousafzai, conducting the sort of in-depth discussions that late-night network comedy shows don’t have the patience to explore. Even in his anarchic heydey, Letterman exuded a no-nonsense Midwestern decency that made him seem more evolved than so many of the comics, stand-ups and talk-show hosts that came after him. He’s practically been crowned the grandfather of modern comedy, a man of integrity who influenced all that followed.

I love Letterman as much as anyone — I was one of those kids whose comedic sensibility was profoundly shaped/warped by his inspired foolishness — but even I sometimes resist this recent coronation. Sure, David Letterman is an institution, but institutions tend not to be very funny. And the real man is far more complicated and compelling, whether we’re talking about his battles with depression or his shocking 2009 on-air admission that he’d had sex with female members of his staff, a confession that very likely (as he himself has acknowledged) would have cost him his job in our modern climate. (Perhaps understandably, that clip isn’t included thus far on Letterman’s page, although it genuinely is one of the most riveting moments of his entire broadcasting career.) 

Those nuances risk getting overlooked when we lionize Letterman on Late Night’s 40th anniversary — which doesn’t mean we should tear him down. But when I click on his YouTube channel, I find myself gravitating toward those early interview clips, where a mid-30s Letterman is stumbling his way through interviewing folks like Larry King or palling around with his old buddy Michael Keaton, both of them trying to suss out what showbiz is all about. 

What people have always loved about Letterman is his authenticity, and those early Late Night episodes are him at his most unvarnished. The comedy bits are still great — elevator races, crushing random things with a steamroller — but he couldn’t hide behind irreverent writing when he was at the desk talking to famous people off-the-cuff. Eventually, Letterman would get the hang of it — he mastered the medium, after all — but that wasn’t always the case. Those messy early years are where Letterman found himself. It’s also where the rest of us discovered what a talk show could be.