Sean Penn on Meeting ‘Reptilian’ Vladimir Putin and Trump’s ‘Angry Used Car Salesman’ Mug Shot

In his new documentary “Superpower,” Sean Penn assesses Ukraine’s ongoing war with Russia and the meaning of the word “freedom” in a world gone mad. He’s also revisits his own past with Russian leader Vladimir Putin, a moment that Penn calls a dark memory from decades before he would meet up with embattled Ukrainian president Volodymyr Zelenskyy.

In the doc, Penn recalls a 2001 visit to the Moscow Film Festival where his directorial effort “The Pledge” was premiering. He and the film’s lead Jack Nicholson had a brief meeting with Putin, a photograph of which is shown in “Superpower.”

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“We did have a chance to talk for about 20 minutes of that night, one-on-one,” Penn told Variety during an on-camera interview about his Paramount Plus original, a companion to Stephen Rodrick’s lush profile of the actor for this week’s Variety cover.

“President Bush had just recently had the famous meeting, where he said he looked [Putin] in the eyes and he knew he could trust him. I don’t think that my insights were any deeper than President Bush’s,” said Penn. “I think he knew how to be impressive and to guide the conversation … he knew that I would be interested. I had two kids, and he talked about his. He talked about Judo, and he talked about things that I’m sure he was well-practiced at talking about, depending upon who his target was, to just not do his country any damage in conversation. He was sort of reptilian, but I would say I didn’t feel an abundance of respect shown from him towards anyone in the room. It was more a, ‘What’s my next move?'”

Bush was not the only American president Penn touched on in relation to Putin. Variety asked about the future of Ukraine’s independence efforts and how it might be impacted by the approaching 2024 U.S. presidential election.

“Far be it for me to speculate who’s going to win the presidential election or even who’s going to be in it. We know what the conversations are and the likelihoods are about all of that. I think that, right now, I’d like to keep my eye on the ball … let’s say one believes it would be awful, embarrassing, dangerous, numbing, stupefying, unloving of our children to elect Donald Trump president,” Penn posed. “That’s not the worst news, because for that to happen, a lot of people didn’t vote, give two shits, or they were too cynical. They [are the people who say], ‘Those guys just want power,’ while themselves doing nothing for the world.”

His on-camera with Variety was conducted in the days following Trump’s August 24 arrest in Georgia, where Trump was charged for efforts to overturn the 2020 presidential election.

“I did see it,” Penn said of Trump’s now-infamous mug shot, “Angry, used car salesman. Failed magician in Vegas.”

Penn has been an entrenched activist for decades, usually spurred by crises like Hurricane Katrina or the devastating 2010 earthquakes in Haiti. His road to “Superpower,” he says, was a bit different. He and producer Billy Smith took interest in Zelensky after his 2019 election win. Penn and Smith wanted to tell this whimsical tale of his comedic actor, who played a president in a comedy, then became the president of Ukraine.” History would ultimately change the tone of the doc, which saw Penn in Ukraine’s capital about to mount production when Russia launched its first attack in 2022 .

We asked that, whatever resolution comes from the war in Ukraine, would Penn ever consider making a scripted project based on his now-friend Zelenskyy.

“It just lucked into the timing of my generation where, when I was at that late teens he girl you love is the movie you’re going to see that weekend. And one after another, they were movies that lasted the ages, like great, great events in cinema. I miss that,” he said, noting the scarcity of global cinema during his youth.

“Today, world cinema’s winning best picture at the Academy Awards, and it’s available and subtitled … on the Zelenskyy story, I would love to see that, but there’s no reason why I should make that. There’s great Ukrainian filmmakers, and we’re ready to see films in foreign languages now, so I think that there’s a great story to tell about that, but it wouldn’t be mine,” he said.

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