Sean Penn Is Esquire's March Cover Star

A rare and candid interview with perhaps the greatest actor of his generation

I arrived early for my interview with Sean Penn, on a Monday afternoon in Hollywood towards the end of last year, and found him outside an office building near the fabled corner of Sunset and Vine. He was with his assistant, Sato. They were sitting on a metal bench by a bus stop, smoking and watching the cars go by. Penn offered me a seat and a cigarette and we talked for a while about the TV show he'd watched for the first time the night before, The Blacklist, with James Spader, whose performance Penn enjoyed.

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It turned out that the notion of watching a TV show was a novelty in itself: Penn has never seen an episode of The Sopranos or The Wire or Breaking Bad or any of the other exalted dramas of the past decade or so. But he'd been left alone for the evening – Charlize Theron, his partner of the past year, had gone out with girlfriends – and, after mulling and then rejecting the idea of calling some buddies for a drink ("They're all in Haiti or Syria") he'd settled down to a rare night in front of the TV. It may have been a surprise to him that he even knew how to work it.

I'd met Penn once before, nine months previously, when I was in LA for Esquire to interview Theron, and I had witnessed then his happy dislocation from current pop culture and technology; he'd squinted with quite magnificent hauteur at an iPad I was trying to manipulate into life so Theron's young son, Jackson, could watch the Disney movie, Frozen. Now he looked at me askance when I made suggestions of TV shows he might enjoy. I was wasting my time – Penn gets his kicks elsewhere.

A week before our meeting, he had arrived back from Africa, where he'd spent a number of months directing a new film, The Last Face, starring Theron as the director of an international aid agency and Javier Bardem as her medic lover. Shortly, he and Theron would be off to Haiti – her first trip to the desperately poor country that Penn has made his second home since the earthquake of 2010. "We like to get out of town," he told me, drily.

Inside the building, we took a lift up to the new US HQ of his Haiti operation, J/P Haitian Relief Organization, of which he is founder, CEO and chairman. Penn employs 350 permanent staff, 95 per cent of whom are Haitian. Today, they were all in the field: other than us, the offices were empty. We sat on opposing sides of a conference table, in plastic swivel chairs. Sato, a no-nonsense Japanese-American woman who has been working with Penn since the Nineties, brought us cans of Diet Coke, which we poured over ice, and a bag of crisps that Penn munched on.

Penn hasn't beaten his addiction to smoking and neither have I, so I put my pack of Marlboro Lights on the table and he nipped out occasionally to pinch another American Spirit from Sato. For good measure, he wore a nicotine patch under his shirt. We ashed in our cups.

Penn is not tall – maybe 5ft 9in – but he is physically imposing: brawny and with an off-balance buccaneer's stride that speaks of a life lived not behind glass and under strip lights but somewhere Out There, where the sun beats down on a man's leathery hide and the wind whips through his thicket of dark hair and the years of exposure to the elements carve deep lines across his brow. On the day I met him, he wore the most insubstantial of pencil moustaches and a tiny triangular wisp beneath his lower lip, like a trainee musketeer.

Penn has a remarkable face: big, bony, obstreperous nose; thin mouth; blue eyes shaded by heavy lids. He has a sharp chin that he leads with, tilting his head, puffing out his chest and pirating out into the world. He is as gnarled and knotted as an ancient California oak.

For our interview, he had on a green combat shirt and boot-cut jeans. To say he looked incongruous in a corporate meeting room would be to understate things in a manner that Penn himself does not favour. As he began to talk, he swung his cowboy boots onto the table and leaned back, squinting through the double-glazing at the panorama: west across Hollywood and Beverly Hills towards the ocean and, unseen in the distance, Malibu, where he grew up.

Sean Penn photographed for Rolling Stone magazine backstage at the Playhouse Theater, Broadway, New York, 1983

There's an almost hallucinatory image of Penn in his new film, The Gunman, a globetrotting thriller in which he plays a former US marine on the run. It shows Penn carrying a surfboard through the war-torn Democratic Republic of Congo. He's shirtless, displaying the discreet torso of Stallone in his Rambo prime. It struck me that, whether intended or not (and this is not a film otherwise filled with sly, self-referential winks or throwaway meta-gags), this shot neatly encapsulates Penn's own unlikely journey from LA surfer to Hollywood bad boy to garlanded giant of cinema and international activist: a man who is happier, by his own account, in a far-flung refugee camp than he is in front of the TV in his LA mansion.

Bare-chested and carrying a surfboard is where Penn first came in, both in life – he grew up almost on the beach – and on screen as Jeff Spicoli, the original spaced-out surfer dude, in Fast Times at Ridgemont High (1982), the film that made him a star.

At 54, he has been working for 35 years and his name is routinely spoken of alongside the greats of screen acting. Perhaps only Daniel Day-Lewis, of Penn's contemporaries, has generated quite so much critical acclaim, and commands such respect from his peers. Penn has twice won the Best Actor Oscar — for Mystic River (2003) and Milk (2008) – and been nominated for it on three further occasions.

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Still he has, he told me, often felt like an actor out of his time, born too late to do the work that would satisfy his ambitions. Penn arrived at a crossroads moment in the story of American film, as the artistic experimentation and seriousness of purpose of Seventies Hollywood was squashed by the blockbuster commercialism of the Eighties and beyond. The second of three sons of Leo Penn, a Jewish actor and TV director who was blacklisted during the anti-communist hysteria of the Fifties, and Eileen Ryan, an Irish-Italian theatre actor who gave up her career to raise their kids, Penn grew up around film and theatre people, and studied acting with Peggy Feury, a former disciple of Lee Strasberg. Even in his early twenties, he was already a throwback to a previous generation of actors, directors and writers.

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He worked in New York theatre before Hollywood film, and socially and professionally he apprenticed himself to the hell-raising stars of the dwindling, almost defunct California counterculture: Dennis Hopper, Jack Nicholson, Bob Rafelson, Monte Hellman, Leonard Cohen, David Blue, Harry Dean Stanton. Later, he was friends with the writers Charles Bukowski and Hunter S Thompson, who described Penn, approvingly, as "batty as a loon".

Initially, Penn was lumped in by the press with the Brat Pack, the loose-knit, cool-haired gang of flashy young actors in early Eighties Hollywood that included Penn's school friends, brothers Emilio Estevez and Charlie Sheen, as well as Rob Lowe, Tom Cruise, Matt Dillon and more. Penn was the baddest bad boy of the bunch. He rode motorbikes. He wore leather. He scowled. He drank. He fell out with directors and studios. He punched paparazzi.

But he was also serious about acting as a craft and film-making as an art – and unlike some of the others, he had talent to burn. Few critics back then made great claims for the performances of his peers – with the exception of the equally intense Cruise – but Penn was recognised early as a committed method actor, researching his roles for months, remaining in character off-set. He was The Talented One.

In 1985, after a brief courtship, he married Madonna, at that time among the two or three most famous and lusted after women in the world. The relationship was tempestuous, not helped by the intense scrutiny of the press. In Macau in 1986, during the shooting of the disastrous Shanghai Surprise, Penn was arrested after allegedly dangling a paparazzo by his ankles from a ninth floor balcony. In 1987, he served 33 days of a 60-day jail sentence – 23 hours a day in solitary confinement – for violating probation he'd been given for punching a fan who tried to get too close to Madonna. The following year, Madonna herself called the police after an argument at their house in Malibu. They divorced in 1989.

Sean Penn with his first wife, Madonna, at a boxing match in New Jersey, 1988

For 20 years following that, with a couple of breaks, he was in a relationship with the actor Robin Wright, best known now for her role on the TV show House of Cards. They married in 1996 and relocated to suburban Marin County, in Northern California, to raise their children away from the celebrity circus of LA. They have two kids: a daughter, Dylan, now 23, and a son, Hopper, 21. They divorced in 2010.

Along the way, Penn became a political activist. For this, in common with other famous frontline Hollywood liberals, he is lionised by some, traduced by others.

Not that he behaves quite like other famous frontline Hollywood liberals. In 1992, during the LA riots, he drove into the teeth of the violence and had a shopping trolley thrown through his windscreen for his troubles. A decade later, he took out ads in the Washington Post and the New York Times opposing the Iraq War. He travelled to Baghdad and Tehran in 2002 and 2003, writing about his experiences for the San Francisco Chronicle. When Hurricane Katrina hit the Gulf coast of the US in 2005, he went to New Orleans, found a boat and a rifle and rescued dozens of flood victims. In January 2010, in the horrifying aftermath of the Haiti earthquake, he arrived in Port-au-Prince with a plane full of doctors and medical supplies and a $1m pledge from the philanthropist Diana Jenkins; he went through about half of it before they fell out. He has been there, on and off, ever since.

His is, by any standards, a life rich in incident and experience. He lives large.

Sincerity – genuine sincerity, not the pose familiar from the red carpets and the talk shows — is a potentially troubling quality, in a man and in an artist, but especially in a celebrity. We've grown unaccustomed to it. We're not sure how to react to it. It's too often confused with earnestness, which is a word that has come to be used pejoratively in our culture of irony and snark. Earnestness suggests humourlessness, narrow-mindedness, lack of sophistication. Sophisticates are cynical and hard-bitten and cruel.

Sean Penn is sincere. He might even be earnest. He's far from humourless — he has a soft, goofy laugh, almost Spicoli-like, that he uses often. And while he's irritable and even jaded, he's no cynic. He's the opposite: a romantic. You'd have to be, I think, to believe in the redemptive power of art and philanthropy and, well, love – as he does.

Famously, he takes no shit. In fact, not taking any shit might be Penn's most marked characteristic. He can be prickly, explosive. The opposite of meek. When he was mocked for his activism by South Park creators Trey Parker and Matt Stone in their geopolitical puppet satire Team America: World Police (2004), rather than keep quiet or play along, he sent back a "sincere fuck you" and offered to take Parker and Stone to Baghdad so they could see the situation for themselves, since they found it so funny. He wasn't kidding.

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What's he like to talk to? Penn tells me he is a fan of road trips. He likes to take off, cross-country, with no specific destination in mind, no route mapped out. He is fond of a motoring analogy, too, so I'll steer towards an easy one: Penn's conversation does not follow a straight road, from A to B. It takes diversions, unexpected twists and turns, unscheduled stops, from A to B via J, with a circle back to D, a quick hop to W, and a brief stop at N on the way back to B. In some ways this makes him a frustrating interviewee. He rarely answers a question with anything approaching a concise, definitive answer. Instead, he circumambulates the topic like a man surveying a used car, kicks its tyres, offers up a quotation from a hero, an anecdote from his youth. How come I enjoyed talking to him so much? For one thing he seemed to be enjoying himself, too. And that's infectious.

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His more outrageous statements made me laugh, which he didn't seem to mind, at all. He's an entertainer. There's a twinkle in his eye. There's charisma and warmth. Even when he was annoyed, he was entertaining. At one point, talking about fame, privacy and the internet, he picked up my Dictaphone and slung it across the table at me, inadvertently (I think) pressing the pause button in the process, robbing posterity of five minutes of quality rant. When I discovered this and pointed it out, he took the news with amused equanimity.

The quotes that follow are intended to reflect a discussion that was sometimes baffling, occasionally impassioned, always lively. We started at the beginning, with no end in sight. I'm not sure we arrived anywhere, but we passed some interesting scenery along the way.

***

1 | "A life i wasn't going to live"

Oh, my childhood was great: Huckleberry Finn with a surfboard.

He was a war hero, yes. But my father was a hero, period. Charlize often says about her son that her number one concern is that he grows up to be a kind person. More than she wants him to be a nuclear scientist, or an activist or anything else: kind. My father was that. That's not easy to be as an American.

It wasn't that I was a serious kid. I was very shy. Socially shy. Not uncomfortably so, not unhappily so, not isolated. I was invited to the parties and I went to them. I just didn't talk to anyone while I was there.

I didn't have a single date in high school. Not one. Take it back. Once. One date that ended in a very shy kiss and then I didn't know what to say the next day. So I didn't have a second date.

They say there's three kinds of people: those who know math and those who don't. Figure out from that which one I am.

I hated school. It was a waste of my fucking time. Preparing me for a life I wasn't going to live.

A lot of people have sob stories in their childhood. I don't. I went through a lot of demon doors by myself. A lot of anger and things that I acted out on and got me in a lot of trouble. I felt troubled for many, many years.

2 | "I don't have any excuses"

I've been led by two things in my life: rage and influence. And one influence would have been this line of EL Doctorow: "The artist's responsibility is to know the time within which he lives."

The rage? I don't have any excuses. I had a very loving family. At 54 years old, I haven't found a shrink who can give me a false memory or a real memory that challenges that.

My assumption is that my personality would have reacted very differently to being blacklisted than my father did. The kind of appreciation he had for the United States came from being the child of first generation immigrants. And his pride in his service for his country was undiminished by that same country, a few years later, keeping him from being able to provide for his family. For five years. He saw it as a growing pain, for the country. There was no bitterness. I aspire to that, but I don't know that I could claim that would be me today.

I'm not a believer in anything, really. And I'm not a disbeliever in anything. Someone says there's a God? It's a punch line to me. Someone says there's not a God? It's equally a punch line. I'm perfectly happy accepting that God, if there is one, doesn't need me to identify His or Her existence.

I know right from wrong. I know what being kind is and not being kind is. I know what I find tolerable and not tolerable. I can have a temper related to people diminishing me or themselves unfairly. Which is usually a simultaneous action. Someone belittles themselves by belittling me.

If I say I celebrate kindness in an interview for British Esquire there are people who would line up to say, "Oh, yeah? Well, when I was on the street and I asked for an autograph for my child…" A three-year-old who had no fucking idea who I was!

There's a lot of power in kindness. I haven't used it enough.

3 | "Tiny little dots"

What's it like to be a celebrity? Probably like being a good-looking girl in New York City or Los Angeles or Rome. Everybody thinks they got a piece of you. They whistle while you walk. We didn't create this. It's been around for a long time. And it's not about celebrity. It's about the diminished sense that people have of themselves.

A star is somebody who goes to Universal Studios on contract and trains in everything from tap to voice to this to that and they can do it all. They goddamn deserve to be called a star. That's a discipline. You're talking about celebrities, man.

My parents knew some famous people. My dad directed TV shows. And they knew people who had gone onto great things from their time in theatre. George C Scott. Jason Robards was the best man at my parents' wedding. But they were not engaged in a celebrity lifestyle. I had a sense of what they did, what the work was, because I'd come to work with my dad sometimes, and that was exciting. But they weren't party people. And then, when I got in I was really culture shocked. But I think about it now and Entertainment Tonight didn't exist. That came towards the end of my first marriage. And there was maybe one magazine: People magazine. Now…

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Paparazzi. I had a lot of that shit because of my first marriage. I always try to suggest to people, forget they have a camera. You're looking at it saying, that camera's following some rich person, that's the price of fame. But if you're willing to consider that the people they are following are human beings, take the camera out of their hands. Just be followed every day all day by somebody. At some point, you might consider homicide, forget about punching somebody in the face. You want your life! And people usually get it when you put it in those terms.

Bob Dylan said the worst thing about being famous is people reminding you who you are on their terms.

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What people are complaining about now is: everybody's a celebrity because of the internet, all of that. And they are talking about privacy. They want their privacy. Fuck you. Your privacy? Your privacy ain't worth shit. Because if it were, you wouldn't buy that fucking magazine. You want your privacy? I've been dealing with that shit since I was 20 years old.

Anonymity is a precious thing, but I don't think anybody has it any more. Roll with it.

I often take great peace in that Neil Young line: "Doesn't mean that much to me / To mean that much to you."

I am, like you, just one of those tiny little dots in a car you see from the airplane. And I feel like that every day. And I like it.

4 | "Can't You Read The Sign?"

In America there's a fear that creates monsters on every corner out of everybody we're not.

I used to drive across country a lot. As soon as I got a driver's licence it became my addiction. And still today, did I not have the obligations I have, I would do more of it. However, it's not what it was once, because there's signs everywhere. Do this. Don't do that. "Can't you read the sign?" Everywhere. On fences. Everywhere. In a mini mall. Everywhere. It's not the open country it once was, and that's just topographically.

In Spain, they take a siesta. A country that's in incredible economic collapse doggedly takes August off. The busboys won't work. They need the money, they won't work. That's when they see family. Well, how incredibly spiritually sane is that, right? Very! We don't have that. So we get very tightly wound. It's the price we pay for being the expeditious, entrepreneurial, capitalist selves that we are.

We don't know how to be patriotic any more without having to fool ourselves that we're number one in the world at everything.

We loathe the narcissism that we're surrounded by because we see it in ourselves. Our culture celebrates everything but humility.

There's so much white noise, so much stuff is full of shit. Without naming names of reality show people, you're so saturated with all of that, all the time, if you're here. You're not saturated with it in Haiti, or South Sudan, or Liberia, or Sierra Leone. You don't want to say being there is healing, but it's clarifying. And with clarity comes everything.

What did I learn from jail? Well, I was in a situation where I surrendered. Meaning I knew I was going to jail and I had agreed with the court on a surrender date. As a result, I was able to pre-submit my reading materials. So I had a sack of books. I'm talking about Raymond Carver – which I don't suggest for jail; little depressing to the essays of Montaigne to a lot of James Thurber. Two days, I'd read everything. I was in an 8 ½ft by 11ft cell, wondering when I was going to get out. Man, you really learn a lot about how you use your time. I also learned how to sleep for the first time in my life. And that lasted until about three months after jail. I could sleep anywhere, any time. And I'd been a lifelong insomniac, and am again. I take some medication for that. I take my Ambien, you know? But I didn't have a cathartic moral advance of any kind in jail. It's just boring.

We live in such a hypocritically polite and puritanical society and the closest I feel to hatred is around that stuff. And I get pretty close to hatred.

I'm in love with a woman and home is where the heart is, right? I'm in love with my children, they're here. Jackson's very committed here with schools and all that. Charlize has friends and family here. And there are upsides and conveniences that come with being here. I'm not a tortured person, being here. And I have access to other places. I know they're there and I'm in constant contact with them.

One of the greatest satisfactions I ever had was watching television and seeing the Dixie Chicks come out after that whole fucking witch-hunt on them, and [singer Natalie Maines] blast out that song they sing: "I'm not ready to back down." And I just sat there, like, "Yes!"

You go down to the Mexican border on a hot Saturday morning. 95°F outside. You'll see no less than 100 people, all of them seniors, many with VFW hats on — Veterans of Foreign Wars — with walkers, waiting to cross the pedestrian gate of the border,
to buy the pharmaceuticals they can't afford to buy in their own country: in Texas, or Arizona. Red [Republican] states, right? Where did I get off on this? I don't know what I was talking about. It was a point I was making relative to something or other.

My world of friends has shrunk. There are people I have great care and affection for I don't talk to any more simply because we took different forks in the road. When I say my closest friends are overseas, they are.

5 | "No time for dogs"

I'm increasingly driven towards the natural world and the disenfranchised world and the underprivileged world and the uncared for world in terms of what it gives me. Notwithstanding what I might believe at times I can give it. It's a reality check in a way that no ego can defy. And God knows, I should know. I have exposed a very strong ego to those worlds and it doesn't play. Which is a great feeling.

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I will tell you that facing the emergencies of Haiti, while hectic and stressful, is the first time I had peace of mind since I was 14 years old. Yeah.

Do I see myself as a romantic? I think it's fair to say that others do. I think there's a very close kinship between romantic and optimistic. I would accept both of those terms as compliments even by those who were using them pejoratively.

There's a word I hate: "humanitarian." I've got someone coming to my desk in a tent in Haiti telling me I'm a piece of shit because I'm not worried about the Chinese who are coming over to steal organs from these dead bodies over here? Well, I've got two live ones over there who might live if I get them to the fucking ambulance, so if you've got five or six dead people who are getting their organs sent to China I don't really have time for that because we've got 72 live ones a day we're trying to deal with. So I'm not a humanitarian to them. Sorry.

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You know, I didn't take any dogs out of the Katrina waters. So I'm not a Peta hero of the year. Sorry! Forty people, we pulled out of the water. So, no time for dogs.

This is our one minute on earth. We're not going to be able to change everything.

In terms of tons of rubble removed from the streets in Haiti, we've made an enormous impact. In terms of lives saved in our hospitals, an enormous impact. One life is an enormous impact, but there's been many. Thousands. Survivors of gunshots and machetes and disease. But poverty goes on. It's not only the poorest country in the Western Hemisphere, it's twice as poor as the next poorest country. And it's an hour-and-a-half from Miami.

We're aspiring to be able to say we made a change. Emphasis on "we" because my organization – by "my" I mean as founder and CEO – is part of something that's also very troubling in Haiti, which is the Republic of NGOs aspect of it. You don't want NGOs in a country. We are designed to be gone in 10 years. And I think we will be able to succeed at that and I will be able to claim something then. But not until then.

When done well, with dignity and care and commitment, movies are a huge medicine, and really important socially and politically, and it can be a very fulfilling thing. I needed something else.

Haiti was an accident. I had been single-parenting my son. I had cleared my slate to do so because I thought I might be single-parenting him through two years of high school. After eight months of that his mother came back into his life, wanted to spend time with him, he with her, and I found myself with a year and four months uncommitted. And four days later the earthquake happened. I went down there to spend two weeks and I saw I could do more and I stayed. Also, my son had had a traumatic brain injury, in that eight-month period [Hopper came off a skateboard]. He was fully recovered by the time he went to see his mother and he's 100 per cent today but he almost died. And there was a lot of pain involved and he had been given morphine in the hospital and to see him have some relief from that pain, that made an impression on me. The first reports of the earthquake were that amputations were happening with no intravenous pain medication. I worked with President Chavez who gave us 350,000 vials of morphine. Met us at the Venezuelan embassy and I got a group of people together to truck it around.

A lot of people would find some irony in the idea of me being a diplomat.

I didn't come back from Haiti, like many of my colleagues did – especially after the emergency phase where it was about dead bodies and amputations – I didn't come back from that, land in Miami and go, "Oh, my God! The materialism is so disgusting!" I'd had 49 years of that before I ever went to Haiti. I knew it really well.

Yeah, I take things personally.

6 | "This is not real life"

Little House on the Prairie. Simi Valley, California. Hot day. Fucking wool suit. I was about 14 years old. I was an extra. Lunch, they all went to get food. I thought, "You're eaters not actors!" And I stayed out in the sun. They came back and said action and I started doing an Irish jig, just trying to keep myself from falling down. I collapsed, from the heat. Lessons in acting…

Acting, to me, is: whatever works. In the theatre it's: whatever works every night. And in the movies it's: whatever works every day, for months.

One of the things I notice today: actors are less willing and ready to be directed. Because they've been given, by the embrace of the culture, a false sense of what their work is: their work is to express what they feel on that day. Bullshit! You know? Bullshit!

I got news for ya, man. This is not real life. There's poetry here. Real life doesn't happen in two hours. And you're hitting a mark so don't tell me that you're that guy. You're hitting a fucking mark and you're in a key light. I don't know where I went off on that.

If somebody's gonna tell me that Daniel Day-Lewis is a less legitimate artist than somebody with some bristles in his hand tied to a piece of wood, you're out of your fucking mind. I'm looking at a guy who has created a dream form to be influenced by and inspired by and excited by. That has significance.

I find more like-mindedness, generally, among older actors. By definition, people who started in the theatre, because less and less do now. I was at the tail end of that, just enough to get caught up in the dream of it. The Actors Studio was still a very vital thing. [Influential theatre producer and director] Joe Papp was still alive. For American actors, that's not a small thing. And you had so many of the greatest generation of transitional actors, who had come from theatre into film. Really a rich time. But also a set-up for extraordinary disappointment. When I started acting in film, it just evaporated: these were writers who had never written a play.

I quit for five years at one point. And Dustin Hoffman says to me, "You're not retired, you're disappointed." He was dead on. That's when I started writing and directing.

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I don't know who the three top acting teachers are in town now. And they were fucking gods, back then.

Baryshnikov was a friend. He was in Irvine, Southern California, choreographing a ballet. We were kind of room-mating for a while at my house in Malibu so I'd go down with him to these rehearsals, and at a certain point it hit me, and it was emotional: they gave up their childhoods, there's no other way the body does this. This discipline, this commitment, is an art. Whether or not you love the aesthetic, this is serious shit. Success is not based on serious shit any more. Someone gets a job on Die Hard 32 because they got a pretty face?

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Why are my movies dark? Fascinations of the moment. The movie I just made [The Last Face] is anything but that. It's tough, because the world of it is tough. But it's about beauty, and it's about love. I had long conversations with John Cassavetes about movies. He was so clear. He says, "I'm not interested in anything else. I'm only interested in love."

The freedom I've found in directing is that as an actor – especially if you consider yourself to have two or three thoughts in your head in the course of the day – you want to find characters and stories that are of immediate interest, that reflect the journey and the questions in your own life. It's been a hard 30 years for that: for looking for those characters and stories. With writing and directing, which is my preferred duty on a film, I'm the one choosing the subject matter I'm gonna live with for the next couple of years.

Over time you have your ups and downs. You get overconfident and then you get self-conscious again. Things happen. And you learn from that. And you adapt. And then comes something like Milk. It was a totally different process from anything I'd ever done or have done since. There was incredible archival footage of Harvey Milk. What you're doing is falling in love with somebody. As a human being, the heart of this guy was so clear. And so I just played the footage for months, every day. Through the night, even if I turned the sound down. And then I went to the set. That's it. Pretty much. That and having a great director and a wonderful screenplay and a great cast around you. But I didn't do anything else.

San Francisco, six in the morning, every morning, making Milk. I'd get to the top of Divisadero with my driver, Chet. We'd stop at the hot wings place at Divis and Lombard, get hot wings, start eating them, just about to hit the Castro, hit the button, boom! "IT'S RAINING MEN! HALLELUJAH! IT'S RAINING MEN! AMEN!" And that was it! We were in the game, all day every day! Just, whatever we thought Harvey woulda liked.

Mystic River, very different situation. You're adapting again. You say, who's [the film's director] Clint Eastwood? What's his vision? His vision of life is jazz music. So what's that? It's a stage. Bunch of strangers get on it, start riffing together. And magic happens. It's not perfect. It's not the way they'll record it later. But man, if you get hold of those tapes with the right group and the right piece of music there's nothing like it, right? So what am I gonna do? I'm gonna tell him no, no I wanna do take 32 even though this other actor's already long burned out on take seven and because I'm gonna make myself better it's gonna make the movie better? I don't think so. I gotta get up there and play jazz. These guys are ready on the so-called rehearsal take. And then he walks away, he's done. Cumulatively, what does that do? You can love or not like Clint Eastwood's movies but he has had a consistent body of work that allows for some things that really touch people at large. I understand a different way to make movies but this is this guy's jazz studio and when you go with it you're gonna get such a cool experience. Then you've got someone like Alejandro [González Iñárritu, who directed Penn in 21 Grams (2003)] who will put you through 48 takes but ask for no more investment from you than he will give, so it feels like you're working and it feels good. Then you also get a lot of jack-offs.

It's not about, do you like your character? It's, are you comfortable in his shoes? I have been desperately uncomfortable in a character's shoes on several movies: The Assassination of Richard Nixon, Carlito's Way. Anybody who's under everybody else in their own mind. That stuff is hard. I'm not being critical of that. Those were the challenges I was looking for at that time. And I could see myself looking for again, rather cautiously.

Alejandro [González Iñárritu] talked to me about doing Babel at one point. I read Babel and, God, I wanted to do it but I knew what it was going to be. From the first scene, you're desperately trying to keep your wife alive. Right? I decided not to do it and he lucked out and got Brad Pitt. And I remember running into Brad at the Toronto Film Festival. Brad had done a lot of movies already. He was a big movie star. He'd done hard movies. But I knew Alejandro. And I knew by then, that's not two hours, that's three or four months of that feeling every day, being pushed by this masterful director who's not gonna take anything less that 100 per cent. And so I ran into Brad after he'd finished it, and been great in it, and he yelled across the room, "You motherfucker!"

They said, "Woody doesn't like to talk to people much." Well, it was a different process [on Sweet and Lowdown] because it wasn't an ensemble. I was in every scene. What happened is it was in the New York Post that we'd been at dinner at this restaurant this one night. So that was unusual. An actor never went out for dinner with Woody. Once in a while an actress but not an actor. I realised I had something here, because those crews have worked with him forever, but they never had a conversation with him. It was an odd family where they never met dad. So I'd come  into the trailer in the morning, like, "Hey! I didn't know Woody could sing!" "Woody can sing?!" "Yeah, I mean because we hit the karaoke bar last night and it was great because we both wore matching cowboy hats and Bermuda shorts. We were doing 'On the Road Again'. He sings really well!" They're looking at each other like, "What?"

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I loved Woody, by the way. He was hysterical. "Eh, Sean, you know what was wrong with that take? E-e-e-e-everything."

We're young when we start, we've got energy to go, we're fascinated with the difficult stuff. You get a life and kids and you're gonna be more selective on those challenges.

As Warren Beatty said, very astutely, "You never finish a film, you abandon it."

You saw The Gunman? What are they showing that to press for? That's not finished. It's not even fucking looped!

7 | "Extremely good terms"

I've had relationships that were not with famous people, or people aspiring to be famous. And in some cases they went more poorly! But as it turned out, yes, the two marriages I had were with high-profile people, in their own ways. But my romantic life has not been exclusive to that.

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One of the underrated versions of opening yourself up to somebody is finding a shared ethic. I have found myself in situations where my ethics were adopted for the period of the relationship and then the floor was pulled out from under me. And perhaps that person would say the same thing. I don't know. I've made a lot of mistakes. And some of that is idealising a relationship or a person in a certain way. Or falling victim to the way they seem idealised. I don't mean by the popular culture but by other people in your life.

I'm very friendly with my first ex-wife. I would say that I'm on extremely good terms with the children I share with my second ex-wife.

Initially, in a divorce, you kick and bite about the other person. But finally you're looking at your failures to that person, to a marriage, to a friendship, to yourself during that time as well. Because no matter what the other person was or wasn't, for better and for worse, it really has so little to do with the growth you need to find better circumstances. Almost exclusively it has to do with your own stuff.

Yes, I'd get married again. You say I've been married twice before but I've been married under circumstances where I was less informed than I am today, so I wouldn't even consider it a third marriage, I'd consider it a first marriage on its own terms if I got married again. I mean, I like the tradition. A friend of mine wrote a line, "Without tradition, new things die." And I don't want new things to die.

Yeah, I'm surprised to be in love. Lot of reasons. I'm self-proclaimed bad at mathematics but I can do two plus two: 53 years old plus finally beginning to figure out why you haven't been happy in a single relationship? It could seem too late. But to run into somebody now who you care about is a much more passionate, deeper, truer and – God! – a much happier feeling. It's a lot more romantic and a lot more fulfilling to be in a relationship and to think you're a good person within it.

Everything is one day at a time. None of us can count our chickens, that's for sure. I get worried every time my kids are driving somewhere, and they're 21 and 23 years old. But we're sitting here today. And today I'm a very happy guy.

I was one of those fathers, when I was out of town, I was on that Friday red-eye, back on Monday. My ex-wife and I worked hard to not work at the same time. I was very present. All of that stuff. But still: there's a lot of time I want back, time I wish I'd spent with my kids. And by the way, we talk about the mistake all the time as it relates to the kids, but it's a mistake for you. Fathers and increasingly mothers, too. And you can't get it back.

My daughter's acting. My son's acted in the movie I just made. He's talented. She is, too. They're both really talented and they're happy. They grew up in a small town, and yet they were exposed to everything. They seem to have a healthy sense of it all.

When my daughter was 16, going on her first date, I practised a long routine. I'd trusted her. She'd been out socially with her friends, but she hadn't dated. And I'd always told her what would happen, but she didn't take me seriously. The day came. She was ready and the guy rang the bell. I said, "Go upstairs, you're not ready yet." She said, "Yes, I am. I said, "No, you're not." I said, "This is my time." "Oh, my God. Dad!" "Dylan, let me be clear with you. I've always trusted you. Your mother and I have been very liberal about letting you do things and you've been very responsible. But you have to go upstairs and not be ready for five minutes. I am going to have this moment as a father, at the door with this guy." So, one more time, she's, "Oh. My. God." And then she went upstairs. She knew I was serious. And I went to the door. And I opened the door. "Oh, Mr Penn!" I said, "Call me Sean." And of course I was two things in that neighbourhood. Three things. Because it wasn't a movie community. I was the radical commie in a right-wing bastion in Northern California. I was the intimidating guy from the movies and from the neighbourhood, who didn't smile a lot or talk to a lot of people. So it was, "Ooh, the scary guy." And I was the father of the girl, which is always what it is. So I said, "Nah, call me Sean." I said, "Dylan should be down in a minute, she's almost ready." I said, "Listen, I want you to have a great time tonight, and I'd prefer you get in early. Although I don't wanna be Mr Controlling on that. You're not going to drink with my daughter, are you? You're not gonna drink and drive?" "No, sir." "Sean, just call me Sean." I said, "Just let me say one thing to you: Whatever you do with my daughter tonight, I'm gonna do with you when you get home."

I'm just another asshole trying to feel good about himself. And why shouldn't I? That's what everybody should try to do.

I can be happy-go-lucky, too.

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