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Sean Penn: The Rolling Stone Interview

Oscar’s bad boy goes off the deep end on art, life, politics and what his kids think of him going gay in ‘Milk’

Actor, Sean Penn, Academy AwardsActor, Sean Penn, Academy Awards

Actor Sean Penn arrives at the Academy Awards nominee luncheon in Beverly Hills, California on February 2nd, 2009.


One afternoon in January, Sean Penn answers the door of his Bay Area home, shoeless, in jeans and a gray thermal undershirt, his hair sort of crazily mussed, looking as if he’s just woken up. It’s a couple of minutes past noon. To say that Penn has “aged well” is to employ a nonstandard usage of the term. He does not look younger than his 48 years. His forehead is baroquely creased, his long face haggard, his hair soaring and gray-streaked and parted down the middle. Something Penn is wearing, or Penn himself, exudes a beer-and-cigarettes musk particular to the morning after a rough night. All of which sounds like the opposite of a compliment, and for many it would be — but Penn has aged into exactly the type of guy he’s always seemed to want to be. When he was younger, not yet anointed the greatest actor of his generation, Penn had a habit of befriending older men he’d long idolized (Jack Nicholson, Charles Bukowski, Dennis Hopper, Hunter S. Thompson) who had, aside from their obvious talents, seemed to figure out a way of living (a way of living very hard) that also became an integral extension of their art. Like the brilliant character actor that he is, Penn studied these men and lived hard himself — fistfights, benders, jail, Madonna, public references to a sitting president’s “soiled and blood-stained underwear.” “I’m not an alcoholic,” he told The New York Times Magazine in 1998. “I’m just a big drinker, and there’s a difference.” You get the sense that Penn would welcome, somewhere down the road, a Bukowski-esque level of physical decay.

Inside the house, Penn’s daughter, Dylan, 17, and a friend are preparing food in the kitchen, where a holiday card from the Coppolas (Francis Ford and wife pictured on the front) hangs on the wall. A massive stone fireplace dominates the living room. (If there is not such a thing as a walk-in fireplace, the term should be invented for this one.) Son Hopper, 15, is nowhere to be seen. In another room, there’s a framed poster of a film noir called Fall Guy, which starred Penn’s father, Leo, an actor and director who was blacklisted in the Forties and Fifties. (To bypass the blacklist, Leo Penn was billed in Fall Guy as “Clifford Penn.”)

Sean Penn has just been nominated for Best Actor for his title role in Milk, Gus Van Sant’s triumphant biopic about the pioneering gay politician Harvey Milk, who in 1978 was assassinated, along with the mayor of San Francisco, by a deranged city supervisor (played in the film by Josh Brolin). It’s another virtuosic performance by Penn, who has amassed nearly 30 years’ worth of them — beginning with Jeff Spicoli in Fast Times at Ridgemont High, one of the few Penn characters, incidentally, who comes to a good end. (And even he blows all of the reward money he gets from rescuing Brooke Shields from drowning by hiring Van Halen to play at his birthday party.) Post-Fast Times, Penn has starred in exactly three comedies: the forgotten Crackers; the excellent, bittersweet Woody Allen movie Sweet and Lowdown, in which Penn plays a 1930s jazz guitarist; and the Robert DeNiro buddy flick We’re No Angels. “I like doing comedies,” Penn says, not smiling, “but I’m not the first guy they go to on that shit.” No, Penn’s IMDb page is mostly bad news: juvie (Bad Boys), death row (Dead Man Walking), war crimes (Casualties of War), murdered daughters (Mystic River), unsuccessful heart transplants (21 Grams), cokehead amateur spies (The Falcon and the Snowman), cokehead Hollywood bottom-feeders (Hurlyburly), cokehead mob lawyers with very bad hair (Carlito’s Way), psychotic fathers played by Christopher Walken (At Close Range) and next up — for director Terrence Malick — the troubled son of a troubled Brad Pitt (The Tree of Life). Which makes Penn’s utter transformation into Milk, a charismatic, unflaggingly positive grassroots activist, all the more remarkable. What’s most surprising is not the fact that Penn is so good at playing a proudly out gay man — it’s that he’s so good at playing such a nice guy. As his friend Brolin (half-) joked in a speech at the New York Film Critics Circle awards, “We’ve known Sean as an actor who doesn’t smile very much. And the fact that you smiled as much as you did in this film is amazing. Truly incredible. You are going to get the Oscar. Because you smiled so much.”

Penn and I spend about five hours together over the course of two days. A decent amount of the time, we drive around Marin County in my ridiculous rental car, a tiny, bright-red convertible. Penn rides shotgun, smoking, sunk low in the seat, often forgetting to give me directions until the last minute, then seeming pleased when I’m forced to cut off other cars or ubiquitous cyclists. (Penn: “Do you ride a bike?” Me: “No.” Penn: “Good.”) When not in character as Harvey Milk, Penn is not exactly generous with those broad smiles. His blue eyes constantly seem to be peering at you over a pair of reading glasses, even when he is not wearing reading glasses, which gives him a perpetually skeptical air. But despite his reputation (moody, hates journalists), Penn is an easy man to get along with. One day at brunch, we’re joined by his wife, the beautiful actress Robin Wright Penn. The next day, we drive out to a Puerto Rican chicken place in San Rafael that Penn loves, taking an outdoor table near the parking lot.

One thing Penn doesn’t want to discuss much is politics. But the topic is inevitable: After he wrote an article for The Nation on his visits with Venezuelan president Hugo Chavez and Cuban president Raul Castro — a longer version appeared on The Huffington Post — he was scolded by a chorus of journalists as being fawning and hopelessly naive, Penn, of course, gives as good as he gets. At one point in our interview, railing about the lack of commitment displayed by some of his acting peers, he says, “People are spending too much time modeling for some fucking clothing company instead of acting, and I resent it. It’s like, ‘I’m sorry — are you going to do the Chanel ad today? I thought you were in the middle of shooting a fucking movie.’

“You see wonderfully talented actors everywhere, which almost makes it sadder,” Penn says wearily, lighting another American Spirit. “It’s not about what kind of movies they make. I don’t care if they make love stories — there arc great love stories. Just let me know you mean it. I want to know you’re trying to write the Great American Novel every time. Fail all you want. But fucking try.”

So congratulations on the Oscar nomination. Did you get up early to hear it?
I’m 48 years old. I turned off my phone and was sound asleep.

Do you get excited by this sort of thing, or is it more about how awards can help a film like Milk reach a wider audience?
Well, we actually got more nominations than we expected. And frankly, the key was Best Picture — that’s very important to getting the movie out there, more so than my category. But I was very excited, because if we hadn’t gotten these eight nominations, we’d be straight to video right now. That’s just the nature of the beast.

When Gus Van Sant first approached you about this film, were you aware of Harvey Milk?
I was graduating high school the year Harvey Milk was killed, so I was in California, and I was certainly aware of it — it was national news, anyway. I didn’t know anything more than this openly gay politician was murdered alongside the mayor of San Francisco. I think it was only a month after the Peoples Temple [Jonestown mass murder] thing had happened, which was mostly San Francisco people, so it was kind of a crazy moment in Northern California.

Did you know gay people as a kid?
I never heard the word “fag” until I was in high school. I might have heard about homosexuals from Life magazine, but I never heard anything derogatory. Politically, it might have been discussed in my home. But it never landed. Did I know gay people? I later came to find out that there were gays in the theater world who were friendly with my family. I remember being at a party as a kid, and Paul Lynde telling my mother how sexy my father was, and thinking, “What’s that about?”

Playing a real-life person like Milk, with so much archival footage to look at, is there a danger of just doing an impression?
Yeah, but I don’t know how to do impressions. I can’t sing, either. So there’s that. The main problem was that normally, to tell a whole life in two hours, you want to get somebody more charismatic than the real person. And in this case, one could only aspire to that.

What’s Van Sant like as a director?
Among the best. God knows, there are directors whom I love, where you get into something one day where a scene’s not working — maybe it’s the writing, maybe your talent’s just not going to be able to rise to it — but at some point, you will point your finger at the director, and on your drive home from work that day, you’re saying, “That motherfucker. . . .” That never once happened with Gus. I have a pretty-photographic memory of attacks I might have made on a scene — whether it was two takes or 30 takes, I’ll remember every one of them. So I have 30 years of going and watching what directors did with those things, how they laid down that track.

You really can watch a film, see a scene and say, “I remember-doing that a different way, and it worked so much better”?
Oh, yeah, yeah, yeah. And Gus has great taste. He’s elegant. You feel that throughout the process.

Besides the script and the opportunity to work with Van Sant, was there political motivation in taking the role?
No. I certainly appreciated the politics of it. But that wasn’t a conscious factor.

It was strange watching the film post-Prop 8 — how eerily it paralleled that fight. And of course in Milk, they win out on the ballot issue, while we’re watching 30 years later having just lost on a similar issue. Were you surprised?
No. Only because I was talking to people in the system, including Mayor [Gavin] Newsom here, who were worried. I was surprised when I heard the numbers among black voters, which was fucking shameful. And, of course, the Mormons. What it comes down to is the churches are not operating like instruments of love. They’re hate machines. They’re ignorance factories.

What do you think Harvey Milk would have become, if he had lived?
The only significant speculation I make is if you look at the timing, what an incredibly powerful voice he would have been when the plague hit, which was a year after. You had an entire administration that never said the word “AIDS.” He would have pushed that issue, and there would be people alive today that aren’t. That seems a pretty safe bet.

Is it known if he had higher political aspirations?
My impression is he would have taken the movement as far as it could have gone.

Josh Brolin made a very funny speech about you the other night at the New York Film Critics Circle awards. Did you guys have an immediate rapport?
We’d spent some drinking time together before we knew we were going to make this movie. He just cracks me the fuck up. And, yeah, we’re both California surfers, we both race cars, we ride horses, our dads knew each other and worked together. I think I might have even met him once, as a kid. I remember going out to James Brolin’s house with my dad. Josh is much younger than I am, though.

What did your dad do with James Brolin?
“Marcus Welby, M.D.”

Did you ever visit your dad on the set of TV shows he was directing?
I was on that show. I was an extra. I had one line. My older brother [musician Michael Penn] and I went in. My brother’s starting a car, and it won’t start, and I say, “You flooded it, dummy.” I was on the set all the time as a kid.

Was that exciting for you, or did it become familiar?
It was a Going to Work With Dad Day thing. I’d venture off into the back lot while they were working, just on my own. That was fun. But I wasn’t dreaming of participating at the time. I was dreaming of being a cowboy but not a movie cowboy.

What was growing up in Malibu like?
I would say it was a combination of Huck Finn and Rumble Fish. It was an idyllic kind of thing. I’d walk to elementary school, about a mile. My feet hit pavement for about 20 feet in that mile. Since then, they’ve built it up — there are more streets. There was a culture of what I’d call soft violence, in the sense that we didn’t let outside surfers surf our beach. We were vandals, we brought wrist-rockets to the beach, beat people up. Some people are kind of shocked by this — but 10 of the guys I grew up with are dead. That’s a big number. This group of surfers — in some kind of Lord of the Flies way, these guys found reasons to put their lives into situations that were horrifying.

Of these 10 people
One lived in Hawaii, came home to Malibu to visit — this is later, in his mid-20s — intentionally ran over somebody with his car, got out of the car, stripped naked and started screaming about God. That was one of them. One guy we surfed with, we used to go to Zuma Beach in the morning before junior high school. We took a bunch of quaaludes before we went out surfing, and he just drifted off into the ocean, and nobody ever found him. Another guy I surfed and played Little League with, he was dealing and doing blow and shot himself off the edge of cliff in a car. Another guy killed his mother. Another guy I was in jail with, actually — I think he’s dead now.

But you saw him in jail?
This is when I was in my 20s. I was in L.A. county jail, and I had a trustee come to my door, and it turned out to be this guy I surfed with. The core group of surfers that I was in the water with for years at a time, that was about eight guys. And there are about half of us left.

Your kids are teenagers now. Have they watched many of your films?
They’ve hardly seen any of them.

By design?
By their design. It weirds them out. They’ve seen a few. They both came to the Milk premiere. I don’t think either one of them has seen more than four movies that I’ve been in. Of my wife’s movies, maybe a few more than that.

But they liked Milk?
Yeah, but the joke was that my son’s problem was seeing his father kiss [James] Franco, and my daughter’s problem was seeing Franco kiss her father.

I heard that Van Sant wanted that first long kiss to happen very early on, otherwise people would be distracted waiting for it to happen. Was that at all difficult to shoot, or just another day?
It was pretty much another day, yeah.

One of my editors — and he meant this as a compliment — compared your playing Milk to Michael Jordan playing baseball, except you were successful. Meaning that you seem to choose increasingly difficult roles, as a way of challenging yourself.
That’s not the way I view it, really. With this character, I assume most of that perception is related to homosexuality. There’s a thing Cleve Jones [a Milk campaign worker, portrayed in the film by Emile Hirsch] said early on. He said gay-rights activists, talking about straights who are sympathetic to the movement, will often say, “They’re just like us — it’s just the sex is different.” And Cleve said, “It’s actually quite the opposite — we’re nothing like you, it’s just that the sex is the same.” And that’s really true. There’s more shared with American blacks — growing up with a level of oppression, and what kind of personalities are bred out of that, either fighters or those who succumb or whatever.

But was it appealing to play Milk, who’s so different from your public persona?
He appealed, period. I liked him so much, and I just thought, “Can I find him in myself?” I didn’t know. And there were times when I’d given it a go and really felt like I failed. You don’t know. You just hope. Something kind of good happened, right as we were about to start. I was finishing Into the Wild at Skywalker Ranch, and Paul [Thomas] Anderson was finishing There Will Be Blood there. So we showed each other our movies. And it was really good timing for me. Seeing Daniel Day [Lewis], who I think is a great, great actor — there’s something rejuvenating about seeing what it is to suit up. I’m not talking about talent here, I’m talking about commitment — I don’t feel challenged by too many of my colleagues in terms of commitment. A lot of them put more effort into selling their pictures than making them. You need people like Daniel Day. Even if you think you’re doing your best work or trying your hardest, he woke me up about, you know, “You’ve got some fucking work to do.” That was very healthy for this movie.

So was it almost a kind of — I don’t want to say “rivalry,” but . . .
No, it would be the opposite of a rivalry. It would be more of a brotherhood. He’s on your team, and he just beat six tackles — now do him a favor and beat seven. There’s something about that that just got the juices flowing.

The first film you directed, The Indian Runner, was inspired by Bruce Springsteen’s song “Highway Patrolman.” What was it about that song that spoke to you?
I thought it could be a movie as soon as I heard it. I spoke to Bruce that day.

Was this after Nebraska came out?
It was before Nebraska came out, because I was living with his sister at the time [Pamela Springsteen, to whom Penn was briefly engaged], so he sent her a rough. We were actually living in an apartment in California that he owned and I was piggybacking on — I was like some homeless guitar player. I called him and said I wanted to make a movie out of his song. I was just a kid, so it was safe for him to say yes. He was like, “OK, Sean, sure.” Probably thinking, “I’ll never be hearing about this again.” But he kept his word.

Have you learned things about directing from directors you’ve worked with?
Oh, yeah. I actually observed Scorsese on Cape Fear. I had just finished The Indian Runner, and I said, “Having just made a movie, I’ve never been more curious about how you do what you do. Can I come down and watch?” I just had to promise I wouldn’t smoke anywhere near him. Asthma. Clint [Eastwood] is a very unusual case. The only thing I learned from him [on Mystic River] was the value of a sense of calm and quiet on a set. How he makes a movie is a mystery to me.

He’s very fast, right?
I remember checking into a hotel in Boston to start on the very first day of shooting. Nine weeks later from that day, the entire movie was finished — including the score that he wrote and recorded! This year, two major pictures, and acting in one of them? I don’t know how he does it.

It’s like a supreme level of confidence.
That plays a big part, yeah. I don’t know what the rest is. He’ll say, “You want to rehearse this scene?” So you get done with your first rehearsal, and he says, “I’m OK. Want to move on?” He’s had the camera rolling — he shot it. I think the most takes I ever did on Clint’s movie was three, and that was rare. A lot of one-takes.

How about the famous scene in Mystic River, where your character is being held down by that huge group of police officers as he tries to get to his daughter’s body?
This is my favorite story of his guidance. In the script, it was written that six guys are stopping me. I thought maybe two of them could take me. But if it’s only six of them, someone might get hurt if I really let myself go, so I don’t know what to do. I don’t want a really fake fight, and I don’t want to hurt anybody. Clint said, “I’ll figure it out,” and that’s all he said. When I came back to the set, he had about 15 guys jump on me, and I was locked down — I was literally able to try to head-butt people, I was able to try to bite people, I was able to try to kick them. I didn’t have to hold back at all, and it freed me to do anything. This is Clint thinking.

What about working with Woody Allen?
[Laughs] He surprised me, because he had written a fairly eccentric character, one that I had never done anything like. And he never asked me what I was going to do until the first day of shooting. If Woody didn’t like something, he’d say, “You know what was wrong with that take, Sean? Everything.” Which was a kind of clarity that made things easy, because you didn’t go and try to adjust what you did — you just changed it. I loved working with him. Certain directors I’ve gotten on really great with. Clint, Woody, [21 Grams director] Alejandro [González Iñárritu], Gus.

An early film of yours I just re-watched was At Close Range, which was incredibly intense. Did you feel like that was your first really substantial role?
That was the first one I was very involved with. I nursed the thing along for five years. I hired the director, Jamie Foley. I had noticed the value of building a partnership between an actor and a director, like with Scorsese and De Niro, certainly. And I was trying to find a director like that, because I had had a few early missteps. Jamie ultimately was not in step with that idea. We were in step on that movie, but he didn’t want to be my director and me be his actor.

I assume that casting your mother [the actress Eileen Ryan] and your brother [Chris Penn, who died in 2006 at age 40] was your doing?
Sort of. Jamie was a close friend at that time, and he knew them both.

Did you and your brother talk much about acting?
As much as anybody, he got me into film. As much as my dad did, he did. I don’t know how old he would have been when he saw Apocalypse Now, but around that time, he became like this Vietnam War aficionado. From the time he was 13 or 14, he was making Super 8 movies, Vietnam War movies, and using Phil Ochs as the soundtrack. He would get on the bus by himself, at a young age, and go to Santa Monica to look for a guy who was the age who might have served in Vietnam. And he’d drag these guys home, these veterans. I’d get home from surfing, and he’d be sitting in his room in a circle of six bearded guys with tattoos, just writing notes, their dialogue, this and that.

And your parents were OK with it?
They loved it. So he started making these movies, then he started including me in them, and then it expanded, and we started making thrillers. At that time, I was still telling myself I was going to be a lawyer. I was reading all of F. Lee Bailey’s books. The Defense Never Rests. I was reading law books, precedents. I wanted to have them all memorized before I ended up going into pre-law. Meanwhile, I had C’s and D’s in school, because I was staying up all night making movies. By that time, I’d had to start acting in the movies I was directing, because there were only six or seven guys you could get out there at night. And they’re dead, too, by the way, most of them.

What was making Taps, your first film, like?
It was a hoot-slash-devastating, because I’d only done theater, principally, prior to that, and the process of film acting, it took me a long time to fall in love with it. On Taps, I was nearly suicidal about it. The director, who in later years I realized was actually quite good and a lovely guy, Harold Becker — I fought with him so much. I must have been a nightmare, because I was so desperate to have the kind of freedom I had on the stage. It takes some time to embrace that. I talk a lot to Nicholson, who really became kind of the angel on my shoulder, as far as directing goes, and a great influence. He says the only reason he doesn’t make more pictures isn’t because he’s tired or getting older. There’s just not that many directors he wants to work with, because it’s got to be somebody you thrive in depending on.

How did you get to know Nicholson?
Tim Hutton [Penn’s co-star in Taps] brought me up to his pad. I guess it would’ve been the year that Fast Times at Ridgemont High came out. It turned out that he and I have a very easy shorthand with each other. He’s stepped it up for me. It’s like you’re speaking the same language but with somebody whose instincts are that much sharper and more experienced.

I’ve read stories about you and Tom Cruise and Timothy Hutton get ting pretty wild during the filming of Taps.
Well, they forced us into a fraternity on that one. They had us set up at this hotel in Valley Forge, Pennsylvania. And we were all kids running around. We had a great time. But since then, I’m always the guy who stays at the other hotel than the other actors stay in. I remember, we were shooting in Thailand on Casualties of War, and some guys were going to the hospital, showing up with stitches.

From being out partying?
It started because groups of young actors can forget what they’re there to do. I didn’t want to get caught up in that.

What was Cruise like to work with?
Loved him.

Any specific memories of what guys got into?
I’d be quite indiscreet if I spoke about it. But in my view, it was all positive. I haven’t seen Tom much over the years, but it’s always a pleasure running into him. And he smoked in Tropic Thunder.

What did you think of Robert Downey Jr.’s speech in that film that references you not getting the Oscar for I Am Sam because you went “full retard”?
All fantastic. Everyone in that movie was fantastic.

Is there something to Josh Brolin’s joke about your uncharacteristic amount of smiling in Milk?
He’s a much more optimistic character than you usually play. The fact of the matter is, when you’ve got a mug like mine, you’re not getting scripts that are calling for smiles that much. But some of it has to be career choices you’ve made. Yeah. And I’m sure part of it is not liking my teeth. It’s choices, and it’s not.

You’ve done so few comedies
That’s not been a choice so much. Even when I did Fast Times at Ridgemont High, years ago, quite a successful comedy, immediately, the next thing I think I got offered was Bad Boys.

I’m surprised they didn’t try to pigeonhole you as
It never happened. I’m more interested in the way drama tends to resonate in people’s lives, versus that kind of escapism. But I certainly would have done 10 more comedies had I been offered them. I was talking to someone the other day and said, “Who would have thought when I was younger that I was going to end up being the poster boy for the Queer Nation and Robert De Niro was going to be the biggest comedy star in America?”

How did you feel, early on, hearing yourself described as a “rebel” or a “bad boy”?
Um, you know, I didn’t read that stuff. The worst of my time in the spotlight was the Eighties, and back then, I was more interested in acting during the day and drinking at night.

Do you think that image of you has stuck to this day, though?
If you’re suggesting that people lock onto a narrative and then have trouble having original thoughts beyond that, I’d say that I’m in in your camp on that one.

Your last film as an actor was All the King’s Men, where you also played a politician, and it’s kind of a funny contrast. Milk feels like it’s presenting the most idealistic vision of what politics can accomplish. Whereas in All the King’s Men, it’s this world of corruption.
A little more Blagojevich going on.

So is your view of politics closer to one or the other film?
I probably have a little of both. It’s funny, All the King’s Men was one of the only times I got blindsided by the reaction to a movie. I liked that movie, and it was loathed and disparaged. I really thought that [director] Steve Zaillian got an unfair break. Even this year the fact that there aren’t crowns on [Steven] Soderbergh’s and Benicio Del Toro’s heads right now, I don’t understand. That is such a sensational movie, Che. Benicio is so fucking good in it. And the fact that I’m not running into these people on this awards-party circuit, it’s crazy.

Do you think it’s the length?
Maybe because it’s in Spanish, maybe the length, maybe it’s politics.

I know you don’t want to talk about politics, but I’m sure you saw the recent columns attacking your
No, I didn’t. I’m pretty out of the loop.

The gist was, they praised you as an actor but said you’re a naive journalist.
Well, I think that they’re professionally naive journalists. I have no regard for 90 percent of American journalism. That’s why I travel and look for things for myself. If you’re going to get on Cuba for its lack of free press, well, we don’t have any press, as far as I’m concerned. We supposedly have the right to it. But we don’t fulfill it. I’m flattered by their disparaging remarks. And with the television guys, a lot of it’s based on actor envy. They’re all a bunch of failed actors. Bill O’Reilly wanted to be an actor more than anything. So they have to diminish it. I’ve heard plenty of actors say, “I don’t like it when actors get political.” They’re just trying to appease these people.

Maybe they don’t want to get boycotted.
Or laughed at. People are more afraid of being laughed at than boycotted. It’s a really cowardly position to take.

Do you have any regrets about not challenging Raul Castro more during your visit on things like the historic repression of gays in Cuba?
I wasn’t intending to paint the whole picture. I was talking about the United States and our gullibility. Just a few weeks ago, I was doing a reading for Paul Newman’s foundation, and we had people outside with “Matthew Shepard, burn in hell” signs. We’ve got a few closet-cleaning numbers to do before we start attacking them.

This is still a homophobic country, no doubt, but it’s different from the history of what happened to gays in Cuba.
But we also lynched blacks all over the South at one time. Did they have massive oppression of homosexuals in Cuba? At one time, yeah. But things change. I’m not a defender of Cuba. But you have to consider the lens you’re looking through.

Is there a conflict between the empathy you need as an actor and the colder eye you need as a journalist?
As an actor, you have to be able to suspend judgment, and instead function within the behavior and the personality of somebody. So I don’t think you’re literally empathizing with some rapist or murderer as much as just accepting the burden of shared humanity with them.

Have you seen other Oscar-buzz films?
I thought about getting out later today, start with Gran Torino and The Wrestler, and then see Benjamin Button later in the week. I run into Clint and Mickey all over the place lately and have to keep saying, “Sorry! I haven’t seen it yet . . .” [In a follow-up interview, Penn said he’d seen The Wrestler: “I wept. Beautiful piece of work.”]

The only one of those I’ve seen is Benjamin Button. Brad Pitt is good, but I found the movie unwatchably sentimental.
Yeah, but I don’t care: David Fincher was robbed on Fight Club, and he deserves whatever he gets. If this one is sentimental, it’s not just some guy jerking oil. You know it’s coming from his heart, as a sincere attempt at dealing with the world.

It seems like the press is pushing an Oscar rivalry between you and Mickey Rourke.
Mickey called me up and said, “There’s this thing. . . .” [Gossip Websites reported Rourke text-messaged a friend to mock Penn’s Milk performance.] I said, “I don’t ever want to read it. It doesn’t matter.”

You’ve claimed not to know how to turn on a computer. Is it to avoid that stuff?
It’s that, and laziness. I could also see myself staying up all night looking up things. But I do feel cleaner without it.

You didn’t act in Into the Wild, but I got the sense that the Emile Hirsch character, his spirit of adventure, was close to
That movie was the closest to my heart of anything I’ve done as a director or an actor. It disgusts me the way they [the Academy] snubbed that picture. We got fucked by our distributor, Paramount Vantage. If we got Academy Award nominations, then they’d invest in the fucking thing. I just thought of the look on that whole crew’s face when nothing came through that morning, with the exception of Hal Holbrook, who should have walked away with the next five years’ worth of Academy Awards. When that morning came, I thought about giving Bill Ayers a call and giving him the address of Paramount Pictures.

Politically, arc you feeling optimistic?
Yeah, I am. I’m optimistic about this man, not about him by himself, and not about his cabinet. But I’m optimistic about the people who put him in office — if they support him first but then challenge him.

As Bush leaves office, do you have anything nice to say about him?
No. I truly think the man should be imprisoned for the rest of his life. I know that sounds like some lefty thing, but I think the state of accountability is a sham. It’s one of my biggest problems with Barack Obama. When Gerald Ford pardoned Nixon, a lot of people were upset about it, but then when Ford died, these Democrats who’d once criticized Ford for that pardon suddenly had these revisionist opinions: “We needed to be unified.” But long term, do you think Bush and Cheney would have gone to the trough like they did if Nixon had gone to jail? No. So when Barack Obama came out militantly opposed not only to impeachment but censuring, I thought, “What the fuck is that for accountability?” Yes, I do think that Obama is a deeply elegant, bright, human person who gives a shit and can do it, who can actually help change the world. But I don’t know yet if all of us are going to do our part.

Do you ever think of moving back to Hollywood, or are you happy here in Marin?
Here’s the thing: I’ve always figured I’d like to die in the tropics. So it really depend son when I sense that coming. What’s in between is subject to a day-by-day reassessment.

In This Article: Coverwall, Sean Penn


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