The Improbable Rise and Endless Heroism of Volodymyr Zelensky

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As I write this, Volodymyr Zelensky, the most improbable national leader in the world, just might be the world’s most popular. By now everyone knows his life story’s surreal outline: a comedian who rose to fame with a portrayal of a president becomes the real thing, then transcends it.

The erstwhile Ukrainian voice of Paddington Bear, the star of a dozen shitty comedies and one decent one, he first stared down Trump over their “perfect” phone call—if you recall, 45 tried making aid to Ukraine conditional on a “small favor,” i.e. a sham investigation into the Bidens, and got impeached for his troubles—and is now staring down Putin on the streets of his besieged capital.

A huge part of Zelensky’s global resonance is that he seems to fit a type everyone knows the world over, because, thanks to millennia of persecution, the type exists the world over: a Jewish wiseacre. The idea of one of those (of us, I should say), becoming a wartime icon is in itself a perfect Jewish joke. It’s Woody Allen in Bananas, it’s Dustin Hoffman in Ishtar, it’s Ben Stiller in Tropic Thunder. Except in real life. Risking real death.

The true story of 44-year-old Zelensky’s rise is a tad more complicated, and speaks more to the incredibly messy cultural tangle that exists between Russia and Ukraine than to any easy stereotype. His business and comedy roots lie in KVN, a longtime Russian showbiz phenomenon whose title is an acronym for a musty Sovietism—“The Club for the Jolly and the Resourceful.” KVN is a bizarre but admittedly original concept: Imagine if sketch comedy functioned as a pro sport, with city teams battling one another for a spot in the major league, and the top matches televised.

Zelensky’s troupe, called Quarter 95, repped Kryvyi Rih—a Ukrainian city—but performed in Russian, which was then considered not only normal but expected. He was team captain (under the nickname “Vovan”). Once Quarter 95 hit the big time on Russian TV, Zelensky and two partners, Sergei and Boris Shefir, formed a production company under the same name. Their studio produced dozens of shows and events for both countries’ markets, including the Ukrainian Dancing with the Stars, which Zelensky himself won in 2006 (and yes, that would be like Simon Cowell winning America’s Got Talent).

Around the same time, Zelensky began to produce, co-write, and sometimes star in trashy Russian comedies, most of them directed by a U.S.-educated filmmaker named Marius Vaysberg. The first one is representative: 2009’s Love in the City, about three friends living it up in New York when a curse from a magic fairy (played, in a moment of either inclusivity or homophobia or both, by flamboyant pop star Filipp Kirkorov) leaves them impotent until they find true love.

Even as he turned toward politics, Zelensky didn’t exactly leave his comedy career in the rearview. His latest and likely last Vaysberg comedy, I You He She, came out in theaters the same month he became president—surely a historic first. Amazingly, on some of these Russian movies, Zelensky worked with the people now de facto wishing for his death: Both his director and his co-star on An Office Romance, Sarik Andreasyan and Marat Basharov, have publicly cheered the invasion of Ukraine.

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