Sean Penn has reflected on his first time meeting Russian President Vladimir Putin following the premiere of his 2001 movie, The Pledge.
Penn, 65, a prominent supporter of Ukraine, dined with Putin and the film’s star, Jack Nicholson, after the thriller-mystery’s opening at the Moscow International Film Festival.
Recalling their conversation during an appearance on Jimmy Kimmel Live! on Thursday, the Oscar-winning father of two said: “We talked about fatherhood.”
Putin shares at least two daughters with ex-wife Lyudmila Aleksandrovna Shkrebneva.
Penn remembered their dinner was “approximately two to three weeks after then-President George Bush said, ‘I looked into [Putin’s] eyes and I felt like I could trust him.’”

“And when I say that, I have to say I was conned also,” the Milk actor added. “I felt that there was something genuine there. Now, we know that he is very willing to kidnap 30,000 kids, murder a lot of people, and teach those kids to hate their parents and their country. And yet, our country isn’t together enough to realize we should give them the resources to defeat him.”
Host Kimmel pushed back, arguing: “I think most of our country is. I don’t know that the people running our country seem to understand that.”
Asked whether he and Putin talked through an interpreter, the Mystic River star said yes, but pointed out that the Russian leader “clearly speaks and understands more English than he lets on.”
“I guess that’s a KGB [the Soviet Union’s former secret police agency] thing,” Penn noted.

The actor and director previously told The Independent about his and Nicholson’s meeting with Putin in 2023.
“We were put in a convoy. We knew that Putin was going to be the honored guest. In the nature of that time and space, we accepted the invitation,” Penn said.

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“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,” he added. “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.”
Since Russia’s full-scale invasion of Ukraine in February 2022, Penn has been among the most outspoken critics of the war.
“Already a brutal mistake of lives taken and hearts broken, and if he doesn’t relent, I believe Mr. Putin will have made a most horrible mistake for all of humankind,” he said in a statement at the time.
“President Zelensky and the Ukrainian people have risen as historic symbols of courage and principle. Ukraine is the tip of the spear for the democratic embrace of dreams. If we allow it to fight alone, our soul as America is lost.”
Penn was later permanently banned from entering Russia over his support of Ukraine.