Sean Penn’s latest film, "One Battle After Another," directed by Paul Thomas Anderson and featuring Leonardo DiCaprio and Teyana Taylor, defies easy categorization. It’s a gripping thriller about political terrorists navigating a near-future America, but it’s also infused with unexpected humor, fierce indignation, and profound empathy. This powerful blend is sure to spark intense reactions, much like Penn himself.
This makes the film a perfect vehicle for Sean Penn, an actor and provocateur who consistently challenges, inspires, and stirs debate. His acting prowess, recognized with Academy Awards for "Mystic River" and "Milk," is well-known. Less conventional are his ventures into gonzo journalism and his vocal advocacy for liberal causes.
Beyond the screen, Penn’s commitment to global issues is undeniable, best exemplified by his long-standing humanitarian organization, Community Organized Relief Effort (CORE), which provides vital on-the-ground assistance in crisis-stricken regions like Haiti, Sudan, and even within the United States.
Our conversation took place recently at Penn’s Malibu home. The room was a tapestry of personal history—photos of family and friends mingling with an impressive collection of knives. His large dog roamed freely, the sounds of plumbers working on his sprawling estate drifted in, and cigarette smoke hung in the air. The 65-year-old actor was everything one might expect: genuine, witty, tormented, a touch irritable, self-aware of his own grandiosity, and as always, utterly unreserved.
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You’re a politically involved person, running a humanitarian aid organization and keenly aware of global challenges. Do you ever grapple with the practical value of making art in such a world? I’ve always felt that all forms of contribution are essentially the same. Whether it’s acting, skilled craftsmanship, or humanitarian aid, it’s about choosing which tool to use to make a difference. If a film helps an audience member feel less alone by recognizing something in a story or character, that’s just as meaningful as rebuilding homes. It’s all connected.
"One Battle After Another" has diverse tones, but I found parts of its depiction of a fascistic, white nationalist America quite chilling. How close do you believe we are to that reality? That’s a crucial question for everyone to consider: What defines America? It has never fully delivered on its promise to all its citizens, and growth takes time – I accept that. While I’m fortunate due to my skin color and gender, it seems progress will be gradual. My father, blacklisted by the country he fought for, never grew bitter, calling it "speed bumps in the making of a country." I strive for that perspective. We face immense unpredictability, ugliness, stupidity, and a detrimental reliance on technology. Perhaps the answer is to embrace it and ask, ‘What can I do tomorrow?’ The fight for freedom has always involved a struggle. Everything celebrated in America emerged from a fight. Why? Because that’s simply what being human entails.
Your character, Col. Steven Lockjaw, is a mix of perversions and insecurities. How did you approach him? There’s a great observation by former Uruguayan president, Pepe Mujica, who challenged the idea that understanding history prevents us from repeating it. Instead, he suggested, history *proves* we are bound to repeat it. True improvement comes not from books, but from experiencing the hell we create. For Lockjaw, I saw a man who reveres lethality and truly *understands* it.
You mentioned in a prior discussion that you’d been disillusioned with acting for about 15 years before working with Paul Thomas Anderson. Actually, it was before working with Christy Hall and Dakota Johnson on 2023’s "Daddio." I received two gifts that year that lifted a 15-year cloud of depression about filmmaking.
What caused that depression? For a long time, I evaluated a film’s worth based on a good script, cast, director, and a subject I’d be interested in seeing. That was enough for a while. But as you get older, you become more aware of the sacrifices. It’s about time, which is finite. It’s not enough to work with people you respect; you seek the same connection you find in family. I wanted to be with people I loved, and that feeling had been absent since Gus Van Sant’s "Milk." So, I kept taking what I thought were good jobs, on good subjects, with good directors, but I missed my family, my dog, and I thought, ‘What the hell am I doing?’ I felt like I might be done with it all.
Do you believe your work suffered during that time? Absolutely. You gain an automatic shield once you’re known for a certain quality. You get away with too much. Marlon Brando once said, "I really have to suit up for that one." I remember doing a play in San Francisco when Marlon called me out of the blue. He said, "You know, opening in a play, to me, would be like summoning the Inquisition." I reached a point where ‘suiting up’ felt like that. To rekindle enthusiasm, to feel your imagination open up again, to connect with the childlike joy of inventing a character—when you lose touch with that and then rediscover it, it’s even better.
Growing up in the ’80s, you befriended figures like Jack Nicholson, Brando, Charles Bukowski, and Dennis Hopper—rebellious and significantly older. What drew you to these relationships? You know that funny thing we do sometimes: ‘What age do you feel?’ From a young age, and still today, it’s very specific: 77. When I look in the mirror, I’m waiting for that guy to show up. My father died at 77, and I had already chosen that age for myself.
Paging Dr. Freud! Might there be a connection? Well, I’ll live longer because he started smoking earlier and didn’t exercise much. But yes, I find it easier to have friendships where you won’t be judged for suggesting a drink. Nowadays, some friends prefer green juice.
Nothing wrong with green juice. Nothing wrong with anything anyone wants to do, as long as it doesn’t harm others. I’m just speaking to my personal enjoyment. I like to share a drink. Also, the people you mentioned were the kind who inspired me about the craft. They were fascinating individuals, incredibly generous as friends, and they supported the types of stories I wanted to tell and how I wanted to work.
I once read a quote from your mother, actress Eileen Ryan, to Woody Allen. You were working on "Sweet and Lowdown," and he couldn’t quite grasp you. Your mom told him, "The thing you need to understand about Sean is that he’s just embarrassed at having had a happy childhood.” [Laughs.] It’s true, I had a very happy childhood. Psychiatrists have tried, pushing to find that capital-T trauma in my youth. It’s not there. I created every ‘demon door’ in my life as a young adult and beyond. I did it myself. My parents were wonderful—a loving family, great brothers, and daily surfing and ocean time. I’ve never been embarrassed about that; I feel incredibly lucky. I was confused for a long time about why I chose to walk through the fires I built, and perhaps still do, but it had nothing to do with my childhood.
I wondered if you felt figures like Hopper or Bukowski represented an ideal artist, and your upbringing wasn’t conducive to that. My childhood had one major flaw: much of it was spent waiting for it to end. This was due to the oppressive system of mandatory schooling, which robbed me of a significant part of my youth. I never had a single productive minute in school. I resent it. You’re miserable, stressed, exhausted, and stuck in a concrete building when there’s a great swell in the ocean. I hated it. Tell the shrinks: it was school. It messed me up.
In Richard T. Kelly’s biography, "Sean Penn: His Life and Times," colleagues describe a deep anger within you. Where does this anger stem from? Look around. I love humanity, but my issue is with humans. You go to the market, and the person at the register isn’t attentive, struggling with the machine while engaging in a lengthy personal conversation with the customer ahead of you. You know that’s not how life should function; there should be a degree of professionalism. You get on an airplane and a flight attendant—
What are you talking about? Incompetence absolutely drives me out of my damn mind! It triggers me to a level you can’t imagine. I start to feel like my soul is a volcano.
Your dog just came in. She knows me. She has to console me.
The biography also recounts a Macau misadventure in 1986, where you allegedly dangled a paparazzo over a balcony, were briefly jailed, and then escaped the country by jetfoil. Please, elaborate. Was a jetfoil waiting? Did you pilot it? It’s like the ferry; they run back and forth all day.
So, it wasn’t that exciting? We were just passengers on the jetfoil. We boarded like normal people and then had to go to a house on the Kowloon side to await a resolution. But about the incident: we never actually dangled him past his waistline over that balcony; there was no intention to drop him. My friend, who was my kickboxing trainer and working as security, overreacted. The guy had something in his hand when he lunged at us, and my friend and I reacted instinctively. Halfway to the balcony, I realized it was a camera, not a weapon. So, as I was pushing him through the open balcony, I yelled, "It’s a camera!" But before we could pull him back, hotel security was on us, grabbing us. We never got to show we weren’t going to kill him. That’s when chaos erupted, and we bolted for the jetfoil. That’s the whole story.
I hoped for a more James Bond-esque jetfoil escape, but mystery solved. You once said, "hypocrisy is the primary experience of American life." How has your own hypocrisy manifested? Daily. Give me five minutes, and I could list ten people who could tell you stories of my incompetence. That doesn’t lessen my anger towards it. What truly bothers me on a societal level is how hypocrisy has recently become intertwined with charisma. We’re dangerously good at celebrating great weaknesses. But yes, I’m not speaking from a position separate from the problem. I suppose I try to live within contradiction. I am certainly willfully contradictory.
Could you elaborate on a contradiction you embrace? Certainly. Ukraine deserves our full support in killing people. That contradicts almost everything else I believe in or would say. But I don’t think there’s another solution. And that’s contradictory.
Penn and I spoke again four days later.
We’re speaking a few days after Charlie Kirk’s assassination—another disheartening event in what feels like America’s ongoing civic degradation. Knowing you take your role as an American citizen seriously, how do you make sense of this moment? As a human, I’m certainly processing what happened. I increasingly struggle to understand why our country has become so accustomed to public polarization, when any of us who truly talk to each other know that such intense partisanship, often amplified by power-hungry politicians and media, isn’t typical of individuals. Regarding Charlie Kirk: this wave of violence feels different. Different from attacks on members of Congress, or an insurance executive, or even the attempt on the president. There’s something unique here. Charlie Kirk, though I didn’t follow him closely and disagreed with almost everything he stood for, seemed to genuinely believe his convictions. I didn’t see him as a charlatan. I think we *need* people like him. We need that debate. We have to fight it out and find compromise. These violent trends do come into fashion, and the way we dismantle them is when people of conscience on both sides recognize that someone who truly believes something is, in a way, your *friend*.
Well, it depends on what they believe, right? I’m not talking about sociopathic Nazism. I mean, if someone believes that human life begins at conception, if you can’t even grasp that concept, you’re ignorant. And if you’re not willing to tolerate that as a deeply held belief, just as I might believe, say, *let the woman decide*. These are all valid opinions. What is the civil consensus in society? This murderer who shot the insurance executive? I’m no fan of health insurance companies, but seriously, is that the best argument you have?
Do you think President Trump has core beliefs? I am not able to discern them.
You made a documentary about Zelensky and Ukraine, "Superpower," released in 2023. Have you spoken to Zelensky since then? Yes.
Do you have a sense of how he understands Trump and America’s actions towards Ukraine in 2025? I think he has developed a very sophisticated understanding of it.
What is that understanding? It wouldn’t be appropriate for me to reveal anything that might reflect on what he communicates to the President of the United States.
How have your own politics evolved over time? I’ve grown less idealistic about humanity, understanding that we’ll likely continue to kill each other for the foreseeable future. However, if your political stance remains unchanged from youth to old age, you’re contributing to the world’s problems. It’s an interesting thought. Years ago, I took my family on a safari to visit a Maasai tribe. They had never seen white people. I remarked to our guide how enriching it was to see such a preserved culture, and he told me, "Don’t do that. Anything that remains static dies." I believe that if this — this Charlie Kirk situation — can be a turning point for our country, it’s about realizing we won’t be what we were before. We can be better, or we can be worse. But the focus must be on shaping the architecture of a new America. That’s where we should invest our hope, encouragement, and imagination, as it’s the only path forward.
On the topic of artists and politics, over 2,000 film industry professionals signed a pledge amounting to a boycott of the Israeli movie industry. Figures like Javier Bardem, Emma Stone, and Joaquin Phoenix were among them. Do you see value in cultural boycotts, and what’s your take on this particular one? I wasn’t aware of it; I was off-grid for a few weeks. Generally, I have an aversion to movements or group actions. If I’m going to boycott something, I prefer to do it independently. However, there’s a time and place for such things, and I would consider it. This one is tricky. Who does it truly punish? What are the implications for free speech? The far-right and Netanyahu pose genuinely criminal problems, which are separate from any positive connections between Israel and the United States. This current Israeli administration is an enemy to every state and to humanity itself. So, I might support it, but I need to better understand its real-world effects before committing.
Has CORE considered offering aid in Gaza? We operate in conflict zones and have been in Ukraine since day one, and we’re currently working in Sudan, so our people understand the risks. But part of my role involves a rational assessment of risk-benefit. My feeling from the outset was that I don’t trust any of our governmental or organizational contacts on either side, and I’m not prepared to ask our team to go there.
Many people engage in politics, but few possess your willingness to be "a man in the arena." Who or what inspired that drive? Muhammad Ali, Bob Geldof, Bono, George.
George Harrison? Clooney.
You can’t just say "George"! That’s a common name! Well, it’s because he’s so prominent in current discussions. You know, Bono—he embodies empathy. He’s an extraordinary human being.
You didn’t mention your father. My hunch is that your drive to contribute to the world stems from wanting to live up to his ideal, given his stand against the blacklist and his heroic service in World War II. Not a pilot; he was a tail gunner and bombardier. I’m sure you’re right; he’s been my hero in every way. Most notably, he remained gentle and never bitter. If I were told I couldn’t work in the country I fought and risked my life for, I think I’d be absolutely seething. Not him. In fact, whenever I *was* seething, he’d listen and just say, "Everybody has their own truth, kid."
We’ve discussed your past struggles with acting motivation and your anger at the world. So, what drives you now? I’m not against feeling intensely frustrated with the world. "The world" — we know what we’re talking about, I think; I don’t want to be grandiose, or I don’t know how not to be. But I don’t even know if I would call what Russia and Putin are doing right now something that evokes a lot of rage in me. I don’t need rage to clearly see how evil and obscene it is. The frustration lies with those unwilling to be clear-headed enough to recognize our sacred duty to support Ukraine’s defense. But I don’t even classify that as anger anymore. I wake up every day with one eye wide open to the environmental threat, the suffering people endure, and my efforts to add value. And with the other eye, from the moment I wake, I see that this is still a magical trick of a beautiful cosmos, and I am going to damn well enjoy it every day — and I do. Apologies to anyone who would wish otherwise, but I am feeling *great*.
This interview has been edited and condensed from two conversations.