Sean Penn: ‘In Ukraine I really had a sensation of what I’ve been missing in the US. It’s really abnormal what we’re doing’

The Oscar-winning actor invites Maureen Dowd into his Hawaii home and chats about his friendship with Hunter Biden, his activism around the world and what happens when ‘the trauma gods’ visit

A still from the documentary with Sean Penn and Ukrainian president Volodymyr Zelenskiy. Image: Courtesy of Paramount+

Don’t mellow my harsh, dude.

I was coming to talk to Sean Penn, the notorious Hollywood hothead who helped launch the word “dude” into the American bloodstream when he played stoner surfer Jeff Spicoli in the 1982 classic Fast Times at Ridgemont High.

I was nervous because the New York Times photographer was already inside the Spanish-style ranch house with Penn, who has a history of throwing punches at paparazzi. I hurried past Penn’s three surfboards and silver Airstream in the front yard, half expecting to see the unpacific denizen of the Pacific Coast wrestling on the floor with the photographer.

Nah. Penn, in dark T-shirt, Columbia utility pants and sneakers, was charming, trailed by his adoring dogs, a golden retriever and a German shepherd rescue puppy.


When I joked that I was relieved to see him treating the photographer sweetly, he laughed. “When I did my 23andMe,” he said, “I thought I might be part Hopi because they don’t like to be photographed.”

Penn, a lifelong Malibu resident, pointed in the direction of his old grade school in the days of a more rural Malibu. He said he gets up at 5:30am and goes, barefoot, out to his wood shop. “I even forget to smoke for five hours.”

As it turns out, Penn has finally mellowed.

At 63, the weathered, tattooed rebel with many causes is a certified humanitarian – riding the crest into dangerous crises around the globe and saving lives in New Orleans and Haiti after disasters – and a crusading documentarian. He started out making the documentary Superpower, thinking it would be a story of how Volodymyr Zelenskiy, a comedian, ascended to Ukraine’s presidency. But then Vladimir Putin pounced.

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Penn ignored the warning of his friend Robert O’Brien, a national security adviser for former President Donald Trump, to “get the heck out of there” and interviewed Zelenskiy in his bunker, hours after the invasion started. He also went to the front lines to dramatise for Americans the story of a young country protecting its democracy against an oppressor, to persuade them to help.

Sean Penn at the Superpower in Berlin in 2023. Photograph: Sebastian Reuter/Getty Images

In 2013, Penn executed a rescue of Jacob Ostreicher, an American business-person rotting in a Bolivian prison after what Penn called a “corrupt prosecution”.

He went all Batman again when the Covid vaccines became available. His organisation, Core (Community-Organised Relief Effort), set up a huge vaccine administration site outside Dodger Stadium.

Penn, still wiry but now sporting a shock of natural white hair with the sides shaved – a do he has for a Paul Thomas Anderson movie with Leonardo DiCaprio – took me on a tour of his house. On prominent display is a painting by Hunter Biden called The Map, the black outline of a head with colourful, detailed brushstrokes all around it. It’s a gift from the president’s son. Hunter Biden,his wife Melissa and their son, Beau, had been over the night before.

Hunter Biden painted it, Penn said, when he was “in pieces” and trying “to put the pieces back together”. Penn could relate.

I went 15 years miserable on sets. Milk was the last time I had a good time

—  Sean Penn

He said the two met in 2022 when Penn gave a speech in honour of U2 at the Kennedy Center Honours. He had read an interview with Hunter Biden, the first “since the chips were rolling down, and I was really taken with him and I told him”. Then last autumn, after a screening of his Ukraine film with big shots on Capitol Hill, Penn had dinner with his friend Republican Eric Swalwell of California, who suggested he look up Hunter Biden in Malibu.

“I had no idea he lived down here,” said Penn, adding drily, “I thought he was off in some judicial-focused place that we see on TV.” He called Hunter Biden “a very, very insightful guy”.

Penn also showed me the pump and hoses he keeps next to the pool. He has been en garde since the Malibu house he had shared with Madonna burned down in 1993.

We did the interview in his man cave, where he likes to serve vodka and talk about the world with his friends. There’s a cosy circle of blue chairs, a sofa and a plywood coffee table Penn made. The walls are chockablock with pictures and letters, including one from his friend Marlon Brando. There’s also a photo of Brando marching for civil rights.

The beach house is not your typical professionally decorated movie star manse. Penn has hung up photos of friends and his kids – actors Dylan (33) and Hopper (30) – with his ex-wife Robin Wright; watercolours by Jack Nicholson; medals that belonged to his dad, Leo Penn, who flew 37 missions in the second World War and got shot down twice; and paintings by his mother, Eileen, an artist and actress, and Hopper. He has a series of headshots above the fireplace of his brother Chris Penn, the actor, who died in 2006. There are vintage posters of the movies of his father, an actor and director who was blacklisted (turned in by Clifford Odets).

Sean Penn at the Cannes Film Festival in 2023. Photograph: Loïc Venance/AFP via Getty Images

And there’s a picture of Andriy Pilshchikov, known as “Juice” and the “Ghost of Kyiv”, a member of a unit defending Ukraine from the air. The charismatic pilot, who was killed in a training accident, was featured in Penn’s documentary.

There are several clocks set to different times around the world, including Ukrainian time.

The room is wreathed in smoke, as Penn alternates between chain-smoking American Spirits and noodling around his mouth with a dental pick. In the bathroom, he displays pictures of his friends smoking, including Dennis Hopper and Harry Dean Stanton, and, justifying his cigarette addiction, the Charles Bukowski quote “Find what you love and let it kill you”.

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The peppery Penn knows a lot of people don’t like him “out of the gate”. He also knows people do not want to be lectured on global ills – and hectored for donations – by celebrities. He knows a lot of fans and fellow artists think he’s a show-off and he should just focus on fulfilling his early promise as one of the great American actors, hone his talent as a director and stop dancing on the world stage with leaders, dictators (Hugo Chávez and Raúl Castro) and even one infamous drug lord (El Chapo, whom he interviewed for Rolling Stone in a wild adventure Penn later conceded was a failure because it failed to spark a conversation on America’s drug policies).

Penn has been mocked and satirised for some of his escapades, but his friend Bill Maher said he’s the “real deal” in a town full of “phoneys”.

Penn wasn’t at the splashy Hollywood fundraiser for President Joe Biden, hosted by George Clooney, Julia Roberts and Jimmy Kimmel. But he was photographed walking barefoot out of the White House state dinner for President William Ruto of Kenya last month. (He’s not a tuxedo type, and his dress shoes pinched.)

“Hunter invited me,” Penn said, noting that he was happy for the chance to talk to Ruto about how Kenyan peacekeeping troops could combat the gangs that have overrun Haiti. He said that violence-ravaged Sudan will be the next country his organisation tries to help.

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But Penn did not press the president on any of his causes.

“I left the president alone because there were opportunities for that when everyone is not tapping his shoulder,” the actor said. He thinks Joe Biden should “take it slow” in the campaign, leaning into an elder statesman role, doing fireside-chat kind of talks, not getting into nasty spats with Trump but giving the nation a sense that red and blue can be united.

He showed me a medallion with the Core motto: “Slow is smooth, smooth is fast, and blood is slippery.”

Of Trump, he said dismissively, “He’s shameful as an art and as a way of life.”

Penn said that the more time he spent in Ukraine, the more he was able to accept people with different political views in our fractured country. He went on Sean Hannity’s show in 2022 to push support of Ukraine, even though Hannity had named him an “enemy of the state” in 2007, back when Penn was lambasting the Bush administration for its Iraq debacle. Penn also did a panel in 2022 with Fox News anchor Bret Baier and O’Brien at the Nixon Library in Yorba Linda, California.

Ukrainians also have political divisions, Penn said, but he was blown away by their “unbreakable” unity in the face of tragedy.

“It’s like breathing a different kind of air there,” he said. “I really had a sensation of what I’ve been missing here. It’s really abnormal what we’re doing.”

Penn escaped more and more into his gonzo journalism and global swashbuckling because he was disillusioned with Hollywood.

“I went 15 years miserable on sets,” he said. “Milk was the last time I had a good time.” That 2008 movie about the murder of Harvey Milk, the first openly gay elected public official in California, earned Penn his second Oscar. (His first was for Mystic River in 2003.)

Sean Penn with his Oscar for Mystic River in 2003. Photograph: Jeffrey Mayer/WireImage

At the time, he got credit for being a straight man playing a gay one, but now there is sometimes an outcry when straight actors get cast as gay characters. I wondered if he could even play Milk now.

“No,” he replied. “It could not happen in a time like this. It’s a time of tremendous overreach. It’s a timid and artless policy toward the human imagination.”

He vigorously rubbed his face to show how he felt on sets, even with good actors and producers, as if he was trying to rub out the experience.

“I feel like an actor who is playing a leading role and is a known actor and is being paid well has a leadership position on a film, and you’ve got to show up with energy and be a bodyguard for the director in some way,” he said. “I was faking my way through that stuff, and that was exhausting. Mostly what I thought was just, ‘What time is it? When are we going to get off?’

“I was sure it was done, but I didn’t know how I was going to keep my house running or travel freely or things like that if I stopped.”

Then his friend and neighbour (and fellow talented nepo baby) Dakota Johnson dropped by with an indie script, Daddio, by Christy Hall, who was also going to direct. It featured only two actors, an enigmatic young woman who gets in a cab at JFK Airport with a driver who’s a street philosopher raised in a hardscrabble Hell’s Kitchen.

“I felt like this could be a pleasant experience, and that’s gonna matter to me now, maybe more than in the past,” Penn said.

Dakota Johnson and Sean Penn arrive for the premiere of Daddio in Toronto last year. Photograph: Geoff Robins/AFP via Getty Images

The driver and passenger engage in erotic taxicab confessions about their personal lives, with Penn’s character sharing some blunt observations. He warns Johnson’s character, a computer programmer coming back from a visit to her small hometown in Oklahoma, sexting with her famous, married boyfriend, that men don’t like to hear the word “love” from their mistresses because the L-word is “not their function”. He notes that “men, we want to look good for other men” and that, for men, “looking like a family man is more important than being one”.

Penn said that when guys come over to his man cave, they make the same sort of blunt judgments about relationships with women that Hall’s cab driver does. Penn’s own feeling is that some feminists still want to be feminine, and some men are “getting feminised”. He thinks dating is getting more transactional for both men and women.

I wondered if Penn, who has been formally coupled and uncoupled with three women – first Madonna; then Wright; and, briefly, Australian actress Leila George, the daughter of Greta Scacchi and Vincent D’Onofrio – and dated several other celebrities, had improvised from his own vivid experiences. (Jewel, an ex girlfriend, called him “a fantastic flirt”.)

He said he just delivered the dialogue as it was written.

He said that he once loved drama in romance. But now, even if he’s madly in love with someone, he said, if there’s any unnecessary drama and visits from “the trauma gods”, his feelings evaporate, like they never existed.

“I look at my dogs and say, ‘Hey, it’s us again.’”

Funnily enough, given how much time he spends helping humans, he once told the Times, “I don’t like humans. I don’t get along well with people.”

When I asked him about that quote, he chuckled and said of people, “They should suck less”.

Despite the encounter with a dread journalist, Penn was in a good mood as I left.

“Happy hour starts at 5:30,” he said with a grin.

This article originally appeared in The New York Times.