Watch Stephen Colbert Get In a Very Tense Conversation With Oliver Stone About Putin


Stephen Colbert might just be the sharpest interviewer on late night television, a canny master of conversation who knows how to steer dialogue from behind, and can come off delightfully charming while still holding his subjects’ feet to the fire. That’s made for a lot of interesting chats on his show, but very few have ever been as jaw dropping as Monday night’s talk with director Oliver Stone.

Stone, the infamous director of movies like Wall Street and JFK, was on the show to talk about his upcoming four-part Showtime documentary on Vladimir Putin. Stone handled nearly 20 hours of conversations with Putin for the project, and Colbert was clearly interested in figuring out just how those conversations went. Early word on the project is that Stone was awfully chummy with Putin—a man who has arrested his political opponents and sent them off to Siberia, jailed political dissidents, supported the murderous regime of Syrian President Bashar al-Assad and, of course, attempted to interfere with the U.S. presidential election.

Stone may be accused of going easy on Putin, but Colbert had no intentions of doing the same in his own interview.

Colbert: Do you like Vladimir Putin? After spending 20 hours with the guy, do you trust him?

Stone: I think you should see the film for yourself.

Colbert: I’m just asking you a question. Do you trust him after spending 20 hours with him? I’d like to see the film, I haven’t had a chance to see it yet.

Stone: He’s a head of state, he has Russian—he has his own interests in Russia. I respect him for that, I understand why he’s doing it. He’s a strong nationalist …

Things only get more awkward from there, as Colbert continues to ask simple, straightforward questions, and Stone dances around the answers. The audience is audibly laughing in shock and disbelief at Stone’s refusal to say a negative word about Putin, and Colbert—usually unflappable—seems a little dumbfounded himself. Asking, ““Anything about him negative you found?” he asked as a follow-up, to laughter and applause. “Anything? Anything? Or does he have your dog in a cage somewhere?”

Stone tried to save face, but remained awfully cagey with his answers.

Stone: Well, you know I’ve always been for free speech.

Colbert: Yes, and it doesn’t seem like he would be a hero of that.

Stone: Listen, no question he’s a social conservative in that way, he believes that [audience laughter] I don’t know why you’re laughing, but it’s—he believes strongly that—

Colbert: Because it seems like a mild description of his behavior. That’s why they’re laughing.

It’s a great interview, but it’s not one that does Stone any favors. By refusing to answer any questions about Putin’s abysmal track record on human rights, he ends up implicating himself as not really caring. That doesn’t necessarily mean Stone himself doesn’t care about Putin’s human rights violations, but if his big documentary doesn’t tackle those in a straightforward way, than how interesting could the documentary really be?