‘Me and Jack Nicholson were put in a convoy to meet Putin’: Sean Penn on his Zelensky film and the future of Ukraine

Sean Penn once met Vladimir Putin. Back in 2001, when he and Jack Nicholson went to the Moscow Film Festival for the Russian premiere of Penn’s film, The Pledge, the president turned up to meet them. Even then, more than 20 years before Russia’s invasion of Ukraine, Penn had a very bad feeling about the politician he now calls a “creepy little bully”.

During their time in Russia, Penn and Nicholson were driven to the dacha (or country house) belonging to Oscar-winning Russian filmmaker and Putin cheerleader, Nikita Mikhalkov.

“We were put in a convoy,” Penn remembers. “We knew that Putin was going to be the honoured guest. In the nature of that time and space, we accepted the invitation. We got in this convoy. And we were going as fast as they wanted to drive, with no care for whether it might have presented danger in the villages we drove through. When farmers with pony-driven carts were trying to come across, the security people in our vehicles would lean out the window to baton them away. It was so needlessly aggressive.”

The car journey gave him “a cold, ugly feeling”. That feeling is expressed at length in the new film Superpower, which Penn co-directed with Aaron Kaufman. Penn started work on the documentary in 2021. It was initially intended as a light-hearted look at Volodymyr Zelensky, the comedy actor who became president of Ukraine. Making it meant that Penn was in Ukraine on 24 February last year, the day when his old host Putin sent his army across the border to try to seize the country.

Penn began work on the documentary with a wry curiosity about Zelensky, the celebrity turned political leader. Now he reveres the Ukrainian leader for staying in Kyiv after the invasion, rather than following American advice to get out of town. “History tells us that they take the ride,” he says. “They get on the fricking Black Hawk and they go to safety. Not him.”

Penn is sitting in a small meeting room on the first floor of the Ritz Hotel in Potsdamer Platz, Berlin, the day after the premiere of Superpower. He looks a little tired. His voice is croaky. His baseball cap is pulled over his head as if to hide his face. His attitude, though, is as fiery as ever. As he reminisces about meeting Putin, he is already thinking forward to the time after the war is won.

“This is going to be one of the really important parts after Ukraine’s victory,” he says. “How do you apply a kind of marshall plan on a culture that has had its imagination so deadened that it needs a totalitarian to live day to day, rather than to allow it to dream and flourish.” He appears to be anticipating a defeat of Russia that will allow for a post-war reconstruction of the country, one that would mirror what was brought about by American aid to Western Europe in the aftermath of the Second World War. He also appears to assume there will no longer be a President Putin in charge.

In the film, Penn is exposed to life and death situations. He sees first hand the devastation wrought on Ukrainian families by Russian bombs. The experience of being there has fuelled a new sense of idealism in him. In our interview (as in the film itself) he talks about the sense of “community” in Ukraine since the war began. “They care for each other. There’s room to disagree. There’s room for a soldier to comfortably criticise his president and know that it is going to be seen on film and know that there are going to be no repercussions,” Penn reflects. He could cite his own documentary as an example. In Superpower, several interviewees he talked to before the Russian invasion of Ukraine were openly hostile or dismissive of Zelensky on camera. They clearly felt free to voice their opinions.

In Russia, by contrast, anyone who voices the slightest dissent is liable to be prosecuted and thrown behind bars. “It’s not unique that people are generally at their best in the worst of times,” he says. “But it is unique that since 2014 [the time of the Maidan revolution, in which the president of Ukraine was ousted as he pursued closer ties to Russia amid large-scale demonstrations] there has been this increasing recognition of the precious value of community.” He talks about the Ukrainian civilians who have stood up against tanks with Molotov cocktails since last year’s Russian invasion. “They’ve tasted freedom. They’re not going to let up.”

To some, Penn’s presence in Ukraine has been aggravating. They regard it as grandstanding, an ego trip for a big-name Hollywood celebrity who can dip in and out of the country with his luxurious Santa Monica home waiting for him between visits. (At the end of the film, Zelensky jokes about coming to visit him there once the war is over). Penn’s sincerity, though, is evident.

The US actor doesn’t hold much hope of a negotiated settlement. “From the Ukrainian point of view, as I think would be the German point of view or the American point of view, should you be spontaneously invaded by an aggressive country and have your civilians, your babies, your mothers and fathers separated, murdered, raped, the discussion cannot be about surrendering territories of Ukraine. The discussion can be about how many [Russians] you’re willing to negotiate to prosecute for war crimes, and how many you’ll allow to save face without conviction. I’d like to see as many as possible of these injustices made right. I think we have two choices. We show the world that bullies with nukes win or we take our chances and fight for the life that we all deserve.”

Penn has been working as hard as he can to drum up support for the Ukrainian cause in America. I ask him how easy it has been to strike up dialogue with some of his fiercest opponents, for example the right-wing Fox News host Sean Hannity (to whom he gave an interview last year to discuss the war). Can that chasm between liberals and conservatives – which widened even further during the Trump era – now be bridged?

“Those dialogues have to continue and not just with Sean Penn and Sean Hannity but with this farmer and this farmer who are arguing at school district meetings and want to threaten and kill people,” he says. “In our country, we don’t have the luxury any more of some kind of political puritanism that creates these divides…”

The secret, he suggests, is for opponents in every walk of life who disagree on 99 out of 100 issues to find the one issue on which they have common ground. He and Hannity bonded over Ukraine and a shared loathing for Putin.

“But it’s entertainment because he [Hannity] and people in his position will change their mind with the political wind. I told him I didn’t trust him. But I do think that on any given day, these people think well of themselves and they are well intended and so we caught a window where we agreed on one thing – and that is to support Ukraine.”

‘Superpower’ stars Sean Penn and Zelensky

Penn is calling for sanctions against Russia to be much tougher and better enforced. Put it to him that American leaders don’t have clean hands when it comes to their foreign policy, and he acknowledges the complexity of the question. “That’s a different fight and one we have to exercise at the ballot box,” he says. He states bluntly that what is happening in Ukraine now is “the least ambiguous war in my lifetime”.

But Penn is withering about how the US lost its way during the Trump era. “We were probably too indulgent in our own bulls***… we became a kind of populist lap dance of a country. When Trump came in, if he had chosen to create a new narrative for Charlie Manson [the criminal behind the Sharon Tate murders], people would be wearing Charlie Manson shirts like they wear Che Guevara shirts. They were just ready… to go with the wind. I am not comparing us to Nazi Germany but I am giving a little understanding of what happened there.”

As you listen to the double Oscar-winning star hold forth about the minutiae of US and Ukrainian politics, you can’t help but think he has come a very long way since he starred as the stoned surfer dude Jeff Spicoli in Amy Heckerling’s Fast Times at Ridgemont High (1982). In the documentary, interviewees talk about movie stars like Reagan becoming politicians. Zelensky himself is an example of this phenomenon. Might Penn follow suit? The question makes him backtrack quickly.

“I like to sometimes wake up at three in the morning, have a short day and then go play,” he says. He begins to sound just a little like Spiccoli, as he explains why, no, we probably won’t be seeing him in the White House any time soon.

I think we have two choices. We show the world that bullies with nukes win or we take our chances and fight for the life that we all deserve

America was probably too indulgent in our own bulls***

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