Sean Penn, Rebel With Many Causes

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 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 un-pacific 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 5:30 a.m. 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 Zelensky, a comedian, ascended to Ukraine’s presidency. But then Vladimir Putin pounced.

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 Zelensky in his bunker, hours after the invasion started. He also went to the front lines to dramatize for Americans the story of a young country protecting its democracy against an oppressor, to persuade them to help.

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

He went all Batman again when the Covid vaccines became available. His organization, CORE (Community Organized 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 colorful, detailed brushstrokes all around it. It’s a gift from the president’s son. Hunter, his wife, Melissa, and their son, Beau, had been over the night before.

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

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

“I had no idea he lived down here,” said Penn, adding dryly: “I thought he was off in some judicial-focused place that we see on TV.” He called Hunter “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 cozy circle of blue chairs and 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; watercolors by Jack Nicholson; medals that belonged to his dad, Leo Penn, who flew 37 missions in World War II and got shot down twice; and paintings by his mother, Eileen, an artist and actress, and Hopper. He has a series of head shots 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).

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.”

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 and 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 satirized for some of his escapades, but his friend Bill Maher says he’s the “real deal” in a town full of “phonies.”

“Sean could search the rest of his life for a script that was even half as interesting as his real life and he’d never find it,” Maher told me. “The rowboat during Katrina, the political prisoners he’s gotten sprung from jail, the years of personally going to Haiti and unloading the food and supplies and getting it to the people. John and Yoko were ‘activists’? Why, they spent a week in bed once? Please, if you look up ‘walking the walk’ in the dictionary, it’s Sean’s picture.

“I didn’t want to get the Covid vaccine, but when I did, it was Sean’s organization that had the whole city coming to the parking lot at Dodger Stadium!”

Doug Brinkley, the presidential historian who worked side by side with Penn during Katrina and went on humanitarian missions to Venezuela, Cuba and Haiti, called his friend “the rebel shaking the rafters on behalf of the underdog.”

He added that what’s easy to forget about Penn, given how serious his pursuits are, is how much fun he can be. “There is no better raconteur around,” Brinkley said. “There is never a dull moment around Sean. He is all forward motion.”

Penn wasn’t at the splashy Hollywood fund-raiser for President 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 told me that violence-ravaged Sudan will be the next country his organization tries to help.

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 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 the Fox News anchor Bret Baier and O’Brien at the Nixon Library in Yorba Linda, Calif.

Ukrainians also have political divisions, Penn told me, 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.)

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 neighbor (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 J.F.K. 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.

The first-time director recalled on the third day of shooting that she got a message Penn wanted to see her. “My heart was pounding,” she said. “He just looked at me and said, ‘Am I giving you everything that you’re looking for?’ I was so blown away by it. For someone of his caliber to care so much about a tiny, little indie two-hander.”

“He’s quite known for being tough and intimidating,” Johnson said, “but there’s a sweet boy in there.”

“There’s a real tenderness in him,” she added.

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 cabdriver does. Penn’s own feeling is that some feminists still want to be feminine, and some men are “getting feminized.” 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 Robin Wright and, briefly, the 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 said 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.’”

He has experienced a fair number of relationships where “the first thing I see in the morning are eyes wondering what I’m going to do to make them happy that day. Rarely reciprocated,” he said.

“On one of my marriages, the background noise of life was a ‘Housewives of Beverly Hills’ or another thing called ‘Love Island,’” he said. “Not even being in the room — I’m not saying this to be cute — I was dying. I felt my heart, my brain shrinking. It was an assault.”

He sees his “friends in the female department” — “beautiful, wonderful people, wonderful with their partners or wonderful on their own” — who show him that relationships don’t have to be dramatic or draining.

He’s not in a serious relationship now and feels “thrilled every day.”

“I’m just free,” he said. “If I’m going to be in a relationship, I’m still going to be free, or I’m not going to be in it, and I’m not going to be hurting. I don’t sense I’ll have my heart broken by romance again.”

Speaking of which, I wondered, what was the truth about the epic fights that devoured his turbulent marriage to Madonna?

“I had a freaking SWAT team come into my house,” he said, sipping his Diet Coke. Madonna told the police she was worried because there were guns in the house. “I said: ‘I’m not coming out. I’m going to finish my breakfast.’ The next thing I knew, windows were being broken all around the house and they came in.” Then, he added, “they had me in handcuffs.”

He said he belatedly realized there were stories circulating that he had “trussed her up like a turkey. I didn’t know what ‘trussed up’ meant, first.” He said he was dating one woman who confronted him the morning after “a lovely night” when he was on the back porch smoking a cigarette. “She’s looking at me like I killed her dog,” he said, asking him “about this hitting Madonna in the head with a baseball bat.”

“I didn’t know what the hell she was talking about,” he said. “Now I think it’s fair to say that I’m not the biggest guy in the world. But if I hit Mike Tyson in the head with a baseball bat, he’s going to the hospital.”

Madonna herself cleared up the matter in 2015. When the director Lee Daniels defended the star of his show “Empire,” Terrence Howard, saying that Howard’s admission that he had hit his wife was no different from what Penn had done, Penn sued Daniels for $10 million, charging defamation.

Madonna provided an affidavit, saying that the baseball-bat and “tied me up” rumors were false and that Penn had never struck her.

“Not only did we win the case,” Penn said about the settlement, “but Daniels wrote a public letter and he had to contribute to CORE.”

About Madonna, Penn says simply: “She’s someone I love.” He said he worked with her on raising funds for Haiti and she recently agreed to do “a really terrific” video for a peace summit about Ukraine.

“It turns out it’s a lot quicker to repair a friendship after divorce if there are not kids involved,” he said. “It took Robin and I quite a while. There was a lot of drama.” He added: “Much more important to repair it if there are kids involved, but no easy swing, right?”

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.

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