Oliver Stone gave a remarkable, tense interview on The Late Show With Stephen Colbert Monday night in which he appeared very reluctant to say anything negative about Vladimir Putin. Stone was there to promote The Putin Interviews, a four-part Showtime series built around more than a dozen interviews Stone conducted with Putin since 2015. It’s a bonkers moment in late-night television—the audience laughed outright at some of Stone’s statements about the Russian president—but it’s also a fascinating look at Colbert’s interviewing technique.
It was clear from the beginning that this wasn’t going to be an entirely friendly encounter. Colbert opened with a clip of Putin telling Stone, “Unlike many partners of ours, we never interfere with the domestic affairs of other countries.”
That’s a nice howler to see Putin deliver on camera—the smirk he gives Stone is amazing—but any thought that Colbert brought it up as an example of one of the telling moments Stone captured went out the window as the clip rolled on to Stone’s not-very-piercing follow-up question: “Thank you, sir. We’ll see you tomorrow to talk about some heavier stuff.”
After that slightly disquieting choice of clip, Colbert gives Stone an incredibly flattering lead-in before hammering him over the head with a very blunt first question. It’s a very well-crafted transition from friendly to tough, even if he does hide behind the “some people say” trope:
We’ve talked a few times over the years. The last time we were here, about three-quarters of the way through the interview, I asked you a question, you said, “Well, that’s a complex subject—I don’t know if we want to get philosophical.”
And I said, “I do want to get philosophical.” When I have an Oliver Stone on, I want to talk about politics, I want to talk about philosophy, I want to talk about what is truth, what is not truth—so let’s talk about Vladimir Putin. You spent 20 hours with this guy, and you’ve gotten a little heat. People have said you’re being too cozy with him, that you believe him too easily. What do you say to the people who say that yours is a fawning interview of a brutal dictator?
Stone’s answer—essentially that politeness mattered because Putin was very busy and Stone needed to maintain his access for the whole two-year project—didn’t really make him look great. But things really went off the rails in this exchange, when Stone tried very hard not to answer a yes-or-no question with “yes” or “no.”
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 …
By the time Stone got to his monologue about how Putin refused to bad-mouth anyone despite being “insulted and abused,” the audience was audibly scoffing, and Colbert wasn’t above feeding off the mood of the crowd. “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?” The final straw came when Stone suggested that Russia was a convenient scapegoat for people who didn’t like Trump. Colbert interrupted him, dropped the “some people say” pose, and spoke for himself:
Colbert: I don’t understand why our president will never say anything negative about Vladimir Putin, given that Putin is an oppressive leader of his country who suppresses the free press and arrests his enemies—that is not something that I as an American or a member of the press can respect. And I’m surprised that you do respect that.
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 brutal. Stone does make one good point, which is that it’s ridiculous to talk about a four-hour film based on a few clips, or even two hours. “What I said is in this four-hour documentary,” he told Colbert. “I think that if you watch it patiently, you’ll see that it’s developed, it’s a film, it has a flow from 2000 all the way to 2017—we went back after the election to talk to him seriously about the election.” He also specifically mentions pressing Putin harder in the fourth episode. It’s possible that Stone established a base of trust with Putin before hitting him with harder questions—in fact, that’s exactly what Colbert did with his ramble about how great it was to talk philosophy with “an Oliver Stone” before asking him if he’d conducted “a fawning interview with a brutal dictator.” But if that’s what Stone was up to, he’s been ill-served by Showtime, which sent critics only the first two hours of The Putin Interviews. And he’s also been ill-served by Oliver Stone, who ended his appearance with this gobsmacker:
The whole “Has he murdered a man?”—I wouldn’t know how to ask him that question, because I don’t—I’ve looked at the evidence too, and if I believed it, I’d go after him.
The follow-up question here is probably “When you say the issue is whether Putin murdered ‘a’ man, which one do you mean?” but Colbert, for the first time in the interview, looks completely dumbfounded. “OK,” he replies after a pause. “Well.” Another pause. “Thank you so much for being here!”