And then he stops. He sees something I haven’t noticed.
“Oh, there you go,” he says.
Penn points to a lonely lens about 100 feet away in the parking lot.
“See the photographer on the other side of the gray truck?” he asks.
In the old days, he responded to the paparazzi in ways that led to lawsuits and arrests. You can purchase a gelatin silver print of Penn, circa 1986, swinging at a photographer who had followed him and then-wife Madonna to their apartment in New York City. On this August afternoon in 2021, Penn doesn’t snap. His expression flattens as he strides to his pickup truck. He’s not being targeted, necessarily. He’s just the most famous person spotted that afternoon by a photographer sweeping an area near the homes of Tom Hanks, Bob Dylan and Julia Roberts.
“They come to check, see if anybody famous is over here,” says Penn. “They’ll collect the picture of me. They’re not going to make a lot of money on that now. They need, you know, Britney Spears, or whoever else they’re paying attention to.”
There is resignation and acknowledgment in his voice. Sean Penn is 61 now. He didn’t mean to get famous, though he somehow ended up more famous than most. He won Oscars in 2004 and 2009, and that seemed to inspire him to have an equally outsized impact off-screen. He went to New Orleans after Hurricane Katrina in 2005, and to Haiti after the 2010 earthquake. One afternoon early last year, Penn was out in front of his house putting a decal on the door of his Toyota Tacoma. The sticker was for CORE, or Community Organized Relief Effort, the nonprofit organization he founded in 2010.
Julia Roberts and her husband, cinematographer Danny Moder, were driving by and stopped to talk. The coronavirus had started to spread, and the government seemed paralyzed.
“And we talked for a while about how terrifying things were, and then I noted his mood and said, ‘You look good,’ ” says Roberts. “And he said, ‘Emergency is my happy place.’ ”
Sean Penn has a film coming out Friday, “Flag Day,” and he should be talking about that. Only that. But that’s not Penn. He is strongly opinionated, with a caveat: He’s not always positive he’s right, and when he’s not, he’s often willing to admit it. What he lives for is the discussion.
This means topics that would make most Hollywood publicists shudder — Harvey Weinstein and #MeToo, race and gender, Susan Sarandon’s Bernie Sanders fixation — are fair game in interviews. Penn will even bring them up. He did not appreciate Sen. Mazie Hirono (D-Hawaii) telling men to “just shut up and step up” during the confirmation hearings for Supreme Court Justice Brett M. Kavanaugh.
“I have feelings about where men stand in the world,” Penn says. “I have feelings about where women stand in the world. I have feelings about where Black men stand in the world, and without those feelings, I’m not human. And to be told you are only allowed to have feelings about your own experience, we all may as well just part ways. It shuts off learning.”
Show business is another sore topic. On the eve of the first movie he’s both directed and starred in, pessimism saturates the conversation. “I want to be optimistic,” he says to an audience assembled for a preview of “Flag Day,” “but I do think the sky is falling.”
Penn doesn’t care much for streaming, “the hybrid exhibition model” or whatever studio execs want to call it. He has an iPad, though he hasn’t figured out how to use it, and you’ll never catch him watching “The Revenant” or “Coming Home” on his phone. (He’s no snob. He does watch TV, and raves about “Succession,” Kate Winslet’s performance in “Mare of Easttown” and Questlove’s debut documentary, “Summer of Soul.”) Over the past few weeks, Penn has been filming a series for Starz called “Gaslit,” in which he plays former attorney general John Mitchell to Julia Roberts’s Martha Mitchell.
But he has not changed the way he feels about movies. He misses the collective experience of sitting in the dark with an audience, knowing that thousands across the country are experiencing, say, “Taxi Driver” at the same time. He misses an era when the best movies were also some of the biggest movies.
“Entertaining is great, but that’s not all a movie should do,” Penn says. “I now find more actors interested in just entertaining than in digging in and revealing anything about human behavior in a serious way. It’s less character-driven, more cool-driven, and an awful lot of mediocrity. And then a lot of things that I just get repulsed by. I mean, like these ‘Fast and Furious’ movies. I wanted to vomit watching a trailer.”
These days, any time he acts he calls it “suiting up.” If he had his choice, he’d devote himself to writing novels, but his two Bob Honey books didn’t move like Harry Potter. By continuing to act, he aims to basically make enough to keep what he has: a modest single-level home in Malibu and a second place in Hawaii. So many of his heroes — Jack Nicholson, Warren Beatty, the late Marlon Brando — slowed their production schedules down after they turned 60. Penn can’t.
“They’re all extremely wealthy and I’m not,” he says.
Penn first talked of quitting in the late 1980s. He was not yet 30 and had graduated from the Vans-wearing surfer dude Jeff Spicoli in 1982’s “Fast Times at Ridgemont High” to star in war dramas, romantic comedies and share billing with Robert De Niro and Robert Duvall.
Whether he really intended to quit or not, Penn started directing in 1991 with “The Indian Runner” and continued acting, taking on roles that would define him, including death-row inmate Matthew Poncelet in 1995’s “Dead Man Walking,” boozy jazz guitar genius Emmett Ray in 1999’s “Sweet and Lowdown” and, in 2003, tormented father Jimmy Markum in the crime drama “Mystic River.” The scene in which Markum’s teenage daughter is discovered murdered proved so painful for Penn, he could not rehearse it. The portrayal would earn him his first Oscar, for best actor.
Not every performance was perfect, not every movie a success. But the choices remained his. Forty years after his film debut in “Taps,” Penn’s résumé includes no superhero movies or parts he took just for the money.
“I think he would literally hurt his soul if he did something like that,” says Dylan Penn, 30, who stars alongside her father in “Flag Day.” “He didn’t start making movies to do that. I think it actually makes it easier when he doesn’t do those roles.”
Bradley Cooper, who got to know Penn through their mutual friendship with De Niro, calls him “one of the greatest actors of his generation” and has such respect for his directing eye, he asked him to watch an early cut of “A Star Is Born.”
“He’s got this willingness to just completely enter into the vulnerability and the flaws of the character,” Cooper says. “I don’t really feel like I’m watching somebody act. I know it’s a weird thing to say — don’t act. The pain that I’m seeing on the screen, I fully believe he’s experiencing it.”
Al Pacino, who starred with Penn in 1993’s “Carlito’s Way,” raves about the music videos he’s directed. For one, in 2016, Penn (working with his friend Sam Bayer) recruited Anthony Hopkins to star in a stunning black-and-white short for Tom Petty and Mudcrutch’s “I Forgive It All.”
As a director, “he’s got the eye, he’s a visionary,” Pacino says.
Pacino also was so mesmerized by Penn’s audiobook reading of Bob Dylan’s 2004 memoir, “Chronicles: Volume One,” that he regularly returns to it.
“I’m with him and I’m with Dylan,” he says. “Right there. The three of us.”
When he talks about moviemaking, Penn will speak nostalgically about growing up in the age of the auteur, when future friends Dennis Hopper, Hal Ashby and Beatty were at their collective best. In his own career, he’ll often talk of 2007’s “Into the Wild” as his peak moviemaking experience.
The film told the story of Chris McCandless (played by Emile Hirsch), who flees the trappings of modern society after his college graduation to thumb rides, paddle down the Colorado River and eventually land in the Alaskan outback. Penn talks of how much has changed since he made the critically acclaimed film.
“Let me put it this way,” he says. “I had eight months to shoot ‘Into the Wild.’ I had 37 days for ‘Flag Day.’ ”
“Flag Day” does not look rushed. Penn and Moder, who served as director of photography, shot it on actual film — 16mm — instead of going digital. For some of the flashback sequences, the pair used Super 8.
The film tells the real-life story of John Vogel, a fast-talking con man who spent much of his life plotting or in jail when a plot collapsed. Penn first read the script 15 years ago and immediately saw his daughter as the star. She resisted. She wasn’t interested in acting; she would go on to work as a fashion model.
Eventually, after some urging from her mother (Penn’s second wife, the actress Robin Wright), she agreed to play daughter Jennifer Vogel.
“Flag Day” almost collapsed. Casey Affleck, picked to play John Vogel, dropped out only a month before filming started. Penn has lost other projects, most notably an adaptation of a Gabriel García Márquez novel he had hoped would be Brando’s final great performance. But this was different. “Flag Day” was starring his daughter.
The closest he got, on such short notice, to finding a suitable replacement was Matt Damon, who read the script and called back excited. But he had committed to “Stillwater” and didn’t have time. He told Penn he was crazy not to act opposite his daughter.
“And I said, ‘Well, you know, I am, whatever I was, 58 years old,’ ” said Penn, noting that in the film Vogel ages from his 20s to his 60s.
“There’s a way to do that digitally,” Damon said.
Martin Scorsese had used technology in “The Irishman” to de-age his actors. But hiring artists from a visual effects studio would be expensive. So Penn gave up his $65,000 salary and threw in more than $1 million more to make the film. He saw no other option.
“Dylan had taken the chance, and there was no way I could let her heart get broken,” he says.
By the time he started filming “Flag Day” in 2019, Penn had pulled back some from CORE. He still hosted the annual fundraising dinner, red-carpet events featuring performances over the years from U2, the Red Hot Chili Peppers and Eddie Vedder, but he was content leaving the management to Ann Lee, a veteran of humanitarian and emergency relief work.
Then the pandemic hit. At the time, CORE’s staff was mainly in Haiti, with only seven workers in the United States. Last spring, Lee told Penn about Matthew Abinante, a doctor who was doing coronavirus tests out of his office in Huntington Beach. They visited him and before long, CORE had established a free testing site at Dodger Stadium. This would expand in time until 2,781 CORE workers were running 47 sites across the country, including in Chicago, North Carolina and the Navajo Nation. CORE would later distribute vaccine doses, more than 1.7 million to date. And Penn began to make his strategic media appearances to urge people to get tested and vaccinated, whether doing a daily update with Los Angeles Mayor Eric Garcetti (D) or going on cable news.
At the Cannes Film Festival in July, Moder sat with Sean and Dylan Penn and actress Katheryn Winnick on a “Flag Day” panel. Nobody asked about 16mm or the use of swing and shift lenses.
“But it was amazing,” says Moder. “Seventy percent of the questions were about his humanitarian efforts.”
Many celebrities give money or take up causes. Penn’s commitment is something different, melding philanthropy with a kind of fearless wanderlust. After the verdict in Rodney King’s beating in 1992, with Los Angeles on fire, he found himself driving into the middle of the riots. After the Sept. 11, 2001, terrorist attacks, he traveled to Iran to write a story for the San Francisco Chronicle and to Iraq to tour a hospital and meet with public officials. He called it fact-finding. Others attacked him for being naive. “The guy’s lucky he can act and should leave it at that,” then-Rep. Peter T. King (R-N.Y.) told the New York Post. “… It gives an acknowledgment to Iraq that it doesn’t deserve.”
Even now, Penn can’t explain exactly what drives his form of extreme volunteerism. Is it his late father, Leo, an actor and director, being blacklisted for supporting the Hollywood 10 after he returned from bombing missions in World War II? Guilt over his success? Boredom?
Former president Bill Clinton, who started working with Penn in Haiti in 2010, has his own theory.
“Instead of asking, I watched him,” says Clinton. “And I think he does it, first of all, because he finds it interesting and he thinks it actually makes him a better actor, a better director, a better artist to know how other people actually live, not to visit and look at it, but to actually know.”
Penn is standing in his front yard when he’s told about Clinton’s praise. He’s honored but shrugs. He’s purpose-driven, yes, but does not believe he’s a humanitarian.
“If I were humanitarian, I wouldn’t have 750 reasons for Greta Thunberg to hate me in my garage, which is my Dodge Hellcat,” he says. (The car’s V-8 engine produces 750 horsepower.)
He also resists analyzing his motivation, shifting the conversation to what he believes he’s skilled at: staying calm during a crisis. He admits to finding satisfaction in clearing a neighborhood of rubble or tearing through the dark streets of Port-au-Prince to get an injured boy to the right hospital.
“I don’t get too flustered when the house is on fire,” says Penn. “I have the right temperament. And when you’re doing what fulfills your temperament, it’s very rewarding.”
Penn’s first high-profile experience with disaster relief was in New Orleans. He went there with a friend, the historian Douglas Brinkley, and waded through contaminated floodwaters to pluck people from their homes. His involvement in Haiti was on another scale. When a 7.0-magnitude earthquake hit close to the country’s capital in January 2010, Penn was transfixed by news reports of doctors being unable to get morphine to tens of thousands of injured victims. This resonated. A year earlier, his son, Hopper, then 16, had been badly hurt in a skateboarding accident. In the hospital, Penn saw how the morphine relieved his pain.
The U.S. government wasn’t going to give an actor 300,000 morphine vials to distribute. This is when Penn’s controversial friendship with Hugo Chávez proved useful. If you can get the drug down there, Penn told the Venezuelan president, I will get to Haiti with trucks and deliver it to trauma centers.
In Haiti, Lt. Gen. Ken Keen, who was coordinating the U.S. relief effort, sent a commander to one of the relocation camps, which would grow to 60,000 people in tents on a tightly packed golf course.
“And he notified me and said, ‘You’ll never guess who’s here. The actor Sean Penn,' ” says Keen. “He basically lived in the mud and the dirt and under a tent.”
Clinton arrived in Haiti soon after. The first thing he wanted to do was meet the people running the camps.
“They’re like mayors of small cities, and there were 10 of them,” says Clinton. “Nine Haitians and Sean Penn.”
In “Citizen Penn,” a documentary released earlier this year, Penn’s time in Haiti is documented by filmmaker Don Hardy. But composer Joseph Vitarelli, who has known Penn for decades, notes there’s a reason the film didn’t come out until now.
“Because Don Hardy was not in Haiti to make a documentary,” says Vitarelli. “Don Hardy was in Haiti to document the activities of the organization.”
And Anderson Cooper, who had arrived in Haiti to report, quickly noticed a pattern to Penn’s CNN appearances, one that continues to this day.
“I met a bunch of people down there who were looking to get on camera, and I ran as far away from [them] as possible,” says Cooper. “But for him, he comes on when there are very specific needs. ‘We can’t get this antibiotic. Or we spent six hours with this kid and what we need is this.’ ”
Lee, a veteran of aid efforts in the Philippines, Kosovo and the Congo, was cool to Penn at first. She wondered whether he was just down there for a photo op. Then two weeks stretched into a month, which stretched into nine months. By 2016, Penn had hired her away from the United Nations’ World Humanitarian Summit to run what was then known as the J/P Haitian Relief Organization and is now CORE. Penn’s great strength, she says, is his unwillingness to settle.
“Because he’s been an outsider to the humanitarian world, I think he can say, ‘Why does it have to be like this?’ ” says Lee. “There’s no ‘How are you guys doing this, are we biting off more than we can chew?’ He’s like, ‘We’ve got to do this.’ ”
A silver Airstream sits in Penn’s front yard. It’s not the one he lived in for a stretch in the 1990s, where he would grill up steaks for Jack Nicholson or Oliver Stone as the sun sparkled over the Pacific.
“When I sold that property,” says Penn, “that trailer was so rotted I just took all my crap out of it and left it there. Then about three months after, these big Malibu fires came through and took it.”
This new trailer was meant to get Penn and actress Leila George to Las Vegas last year so they could get married. Until the coronavirus struck. So in July, Penn and George had a ceremony at home and spent the night in the Airstream on pillows monogrammed with their initials.
It’s a Sunday afternoon, and the weekend has been taken up by a Penn retrospective at the American Cinematheque that includes screenings of “Flag Day” and a Q&A with Penn and his daughter. (His son, Hopper, now 28, has a smaller acting role in the film.) It is here, after he talks of the incredible satisfaction he takes in knowing that his latest film will open in theaters first, that Penn offers a caveat. If you are not vaccinated, he says in every interview and appearance, stay away.
He also can’t help but deliver his doomsday view of the business he fell in love with. Beatty, his longtime friend, is more philosophical as he considers the pros and cons of the shift from traditional theatergoing to streaming. Beatty knows Penn is frustrated. But you can’t turn back time.
“We are now required to approach movies more in the way that we approach books,” says Beatty. “There is a library. And it’s a great luxury to have in our library the availability of a movie, let’s say, by Jean Renoir or Orson Welles.”
“But it would be even better to be seeing those on a big screen with an audience.”
Penn can’t see this balance.
He knows home video has democratized the business. He understands that digital technologies have made it easier and cheaper to make movies. He also knows that nothing can replace seeing “Raging Bull” with his pal Joe in a New York City cinema — no bathroom breaks or Twitter scrolls to distract from De Niro’s washed-up boxer.
“I find myself mourning all the time,” says Penn.
The magic was in being in that theater, committed to his relationship with the big screen. “The only way I can describe it,” he says, “is that I don’t fall in love with two people at the same time. When I’m in love with somebody, that’s who I’m in love with.”
About this story
Editing by Janice Page. Photo editing by Moira Haney. Copy editing by Matt Schnabel. Design by Beth Broadwater.