David Letterman Brings His Outsider Perspective to a Sitdown With Volodymyr Zelenskyy

David Letterman’s stated goal in returning to television after his retirement from the late-night scene in his Netflix show My Next Guest Needs No Introduction is a simple one. At the beginning of his highly anticipated sitdown with Ukrainian President Volodymyr Zelenskyy, which is now streaming on Netflix, the 75-year-old TV icon offers this succinct summary: “I would really like to meet this guy.”

And so, in October of this year, the American TV host met the former stand-up comic and sitcom star turned president in an active subway station, 300 feet below the streets of the besieged Ukrainian capital. (That Zelenskyy’s series Servant of the People saw his everyman improbably becoming president is addressed, with the president joking, “Just between us, I don’t think I’m capable,” when Letterman asks if this was his plan all along.) Letterman notes that it was Zelenskyy’s address to the world at the start of the war in which the 44-year-old president stated, “This may be the last time you see me alive,” that spurred Letterman to pack up his Worldwide Pants production team for a trip into a shooting war. The setting for this interview underscores just how little has changed in the months since Russian President Vladimir Putin ordered a full-scale invasion of Ukraine.

Letterman notes that Kyiv was struck by Russian drones and missiles mere weeks prior, and, just as he and Zelenskyy sit down on their subway platform makeshift studio, an air raid siren can be heard echoing through the tunnels from above. “What should we do?,” Letterman asks. “Nothing,” says Zelenskyy, as they fiddle with their earpiece translators and wait for the alarm to finally fade. There’s a moment midway through the interview when Zelenskyy notes playfully that he and Letterman have accidentally swapped their water bottles, leading to a jittery laugh, Russia’s long history of political assassination suddenly the elephant in the room. The Ukrainians packed in to watch this odd encounter are dressed alternately in civilian clothes or helmets and camouflage, underlining Zelenskyy’s assertion that, in a Ukraine under attack, the line between soldier and civilian has necessarily blurred, if not disappeared.

In My Next Guest Needs No Introduction, Letterman still interviews his share of big name entertainers, his status as talk show legend emeritus giving him his pick of the notables he’d also just want to meet. But in these more intimate and extended interviews, Letterman’s curiosity drives the conversation freed from network interests, his midwestern outsider sensibility not only maintained but strengthened over the years. So it’s fascinating to watch him opposite Zelenskyy, whose own performing and comedy background suggests a canniness of messaging; Letterman’s clear admiration for the Ukrainian leader leaves viewers alert to the uniquely loaded situation.

Letterman brings up the currently precarious state of democracy in America, with Zelenskyy noting that Ukrainians are acutely aware of how the balance of power here will, in a very real way, determine the fate of the war. Letterman, with the homey bewilderment he memorably expressed after the 9/11 attacks, wonders aloud how anyone could choose authoritarianism, with Zelenskyy noting that it’s only when Americans are faced with the “wide-scale isolation” that dictatorships face from the rest of an increasingly interconnected world that they will fight for democracy. The Ukrainian president specifically references Russia being excluded from things like the Oscars and the World Cup, feelingly telling Letterman, “Russia has become a symbol of emptiness.”

Here, the specter of an American entertainer being used for political purposes (think Oliver Stone’s infamously slavish 2017 Putin interviews) hovers. While Letterman’s admiration for his guest is evident, Zelenskyy’s carefully considered answers are clearly crafted to reinforce the inspirational image that drew Letterman to Kyiv in the first place. Meanwhile, the queasy possibilities of wartime nationalism abound. An interlude to a Kyiv comedy club (where Letterman does a brief set) sees a young Ukrainian stand-up prefacing his material with a call and response where the audience chants, “Death to the enemies of Ukraine.” Zelenskyy tells Letterman a somewhat rambling joke himself during the interview, where the punchline turns on 70,000 dead Russian soldiers.

It’s not that Zelenskyy doesn’t come off as anything but the stalwart defender of his country that he’s been portrayed as since the beginning of the war. The Ukrainian leader is emphatic and even poetic in describing how war forces people to make an impossible choice, the president referencing the widely reported war crimes and other atrocities of the Russian invaders. In another interlude, we see Letterman being escorted past the burnt-out husks of captured Russian tanks, the host visibly blanching when told that they came from the ravaged town of Bucha. “Everyone in the U.S. knows of Bucha,” says the shaken Letterman. In the interview, Letterman sits terribly still as Zelenskyy says of war, “It creates the conditions in which you have to choose to either remain human or turn into an animal, a terrorist, a marauder, a rapist,” concluding that staying human in such times “is a hard choice.”

That’s incredibly weighty stuff for even this wizened and selective Letterman to confront, and a test of how his own carefully fashioned outsider’s perspective fares in the chat show format he helped shape. A postscript Zoom interview sees Letterman confronted with the added knowledge of Russian war crimes in attacking Ukrainian infrastructure and power, just as the region’s unforgiving winter locks the embattled country down even further, with Zelenskyy calling the Russians “barbarians.” It’s clear that Letterman’s intent is to boost all-important American support for Ukraine, and his questioning lends itself to the messaging that Zelenskyy wants. But, as both men note at times throughout this compelling encounter, messaging has become one of the most powerful and essential weapons in the war between democracy and authoritarianism.

My Next Guest Needs No Introduction With David Letterman and Volodymyr Zelenskyy is now streaming on Netflix. You can join the conversation in our forums here. 

Dennis Perkins is a freelance entertainment writer with bylines at The A.V. Club, Paste, Ultimate Classic Rock, The Portland Press Herald, and elsewhere.