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David Letterman Is Still Adjusting to 2018

The first episode of his Netflix show—featuring a meandering, hour-long conversation with Barack Obama—is equal parts introspective and charming

David Letterman Netflix/Ringer illustration

There’s a moment at the end of David Letterman’s interview with Barack Obama that brings the entire preceding hour — a rambling, enjoyable, strange piece of television — into focus. For the final question, the 44th president of the United States turns the tables on his interrogator. Looking back on both his and Letterman’s careers from retirement, Obama asks, “Don’t you say to yourself, ‘Boy, I feel lucky?’”

It’s a softball, but Letterman takes the query seriously. Their conversation, the first of six to be released by Netflix over the next six months under the name My Next Guest Needs No Introduction With David Letterman, has been sprinkled with interstitials taped in Selma, Alabama, in which Letterman walks across the Edmund Pettus Bridge with veteran civil rights activist and U.S. Representative John Lewis. In the moment, the segments feel well intentioned but awkward, interrupting the flow of the main exchange to delve into subjects Letterman doesn’t seem fully comfortable addressing, like the roots of racism and the arc of history.

With Letterman’s answer, though, Lewis’s cameos begin to make sense. While Lewis and his compatriots were risking their lives by crossing that bridge, Letterman recounts by way of explanation, he and some buddies were headed to a booze cruise for the Bahamas. The contrast is funny; it gets a few laughs from the sizable live audience. But mostly, it makes Letterman sad. “Why wasn’t I in Alabama?” he asks, almost plaintively. Subtext: What have I done to deserve all this, while the world goes to shit?

David Letterman, like many of his peers, feels compelled to do something. It’s just not clear yet what that something is.

Obama’s successor is never mentioned by name in this first installment of My Next Guest. The closest Letterman gets to invoking him is in one of his exchanges with Lewis. “Without being too specific about it,” he begins, “how much of a setback is the current administration?” (Pretty big, though America’s overall trajectory is an upward one, Lewis says.) Nevertheless, President Donald Trump looms large over My Next Guest, as he does over everything these days. In conversation with Obama, Trump lingers beneath more general topics like Russian election interference and the spread of misinformation through social media. His shadow falls on every mention of what Obama would like to do next, what he’d still like to change about the country but no longer can. And he’s evident in Letterman himself, whose sarcastic quips about how Obama’s still commander-in-chief feel almost compulsive.

There are a few different interviews floating around inside the 56-minute episode — though edited down from a significantly longer raw tape — available to Netflix subscribers starting Friday. This includes some registers more typical of post-presidential unwindings that would dominate had Letterman and Obama’s summit been recorded under different circumstances. There’s the just-two-pals-who-are-also-wealthier-and-more-powerful-than-you-could-ever-imagine approach; after all, as Letterman states at the beginning of the interview, both have “recently left long-term jobs,” albeit under different circumstances. Shop talk of exotic vacations and sudden reserves of free time abounds, and just when things threaten to cross over from aspiration to alienating, the men settle on the more universal common ground of parenting. Have some Kleenex ready for the “dropping Malia off at college” story.

There are also traces of a more sweeping, biographical, practically Maronesque discussion. Letterman goes all the way back to Obama’s dead mother, his globe-trotting childhood, and his decision to go into social justice and organizing as a career path. These stories constitute another recognizable kind of after-office interview: the one that puts an entire political life, now effectively finished, in perspective with the benefit of hindsight. One of Letterman’s tactics celebrates Obama as the newly normal dude futzing with his coffee maker; the other, Obama as the very-much-not-normal-man who can now apply his legendary rhetorical skills to what he just went through.

A former head of state — one Letterman has a preexisting relationship with, as the opening sequence is careful to remind us — is a logical booking choice for Letterman’s first post–Late Show hosting gig. There’s chemistry; more importantly, there’s cachet, highlighting Letterman’s status as an elder statesman reaping the rewards of his hard work and edging Netflix ever closer to entertainment hegemony.

But in other ways, Barack Obama, and particularly Barack Obama at this present political moment, is not as obvious a fit for My Next Guest as he first appears. Though Letterman hosted presidents on his CBS show, he has never been an especially political comedian. As New York Times comedy critic Jason Zinoman writes in his essential Letterman: The Last Giant of Late Night, the entertainer idolized the famously neutral Johnny Carson. Letterman’s subversion of the format, which peaked with his tenure at Late Night from 1982 to 1993, was always more tonal than principled, a pattern that extends to his earliest work. “Letterman cared more about partying with friends than political activism,” Zinoman writes of the same period the host now voices explicit regret for, “but he became a campus radical of another sort. … What he shared with the sixties youth culture was irreverence in the face of authority and an aggression that didn’t mind if it was alienating.”

The days of “Stupid Pet Tricks” and even “Top Ten Lists” are long past. My Next Guest is no rebel’s attack on the establishment; Netflix is not the offscreen bogeyman to My Next Guest that NBC and its gray-suited executives were to Late Night, one token joke aside. The template is simple, designed to emphasize the parity between Letterman and his über-famous guests like Obama and subsequent invitee George Clooney. There’s no desk, and no Paul Shaffer–fronted band; just two chairs, facing one another on a bare-bones New York stage.

Without too much of his historic smart-aleck persona, Letterman is left with a newsman-like role that he’s still getting used to. His lack of experience with complicated issues like racial oppression tends to show, whether in awkward questions like “Barack Obama would have been with you [on the bridge] if he had been the right age, wouldn’t he?” or what the root cause of racial prejudice is. (We don’t see Letterman ask Lewis about this, but he later paraphrases their exchange to Obama.)

In fairness to Letterman, the weighty agenda comes as much from Obama as his interlocutor. The common link between Obama and Lewis, beyond their awkwardly stated shared identity, is a shared interest in voting rights, which Obama plans to advocate for with an anti-gerrymandering initiative in partnership with former attorney general Eric Holder. Letterman’s simultaneous eagerness to dive in and trepidation about doing so are precisely what makes My Next Guest so fascinating to watch. Such are the Trump administration’s extremes that they’ve prompted one of our most iconic entertainers to do some soul-searching at the very moment he should be resting on his laurels.

It’s also possible that the reasons for Letterman’s introspection are as much internal as external, and we’ll likely get more insight into his state of mind over the coming months as Netflix releases his sit-downs with the likes of Tina Fey and Jay-Z. At 70, Letterman is now the age when one starts asking questions like, “Why wasn’t I in Alabama?” He hasn’t found an answer yet, but it turns out that David Letterman is just as curious — and a little bit anxious—about who David Letterman is in 2018 as we are.