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Sean Penn: Cool Jerk

How the Oscar-winner reconciles being the best actor of his generation with being a menace to society

Robin Wright, Sean Penn

Robin Wright Penn and Sean Penn at VH1 Honors April 29th, 1996.

Jeff Kravitz/FilmMagic/Getty

Sean Penn is famous for acting like an asshole. He has done it professionally, of course, in such movies as Bad Boys, At Close Range, Carlito’s Way and now Dead Man Walking, his best performance — justly Oscar nominated — in an already inspired career. Yet he has also managed to retain his amateur status by having sucker-punched photographers, failed breathalyzers and logged his share of jail time, most notably the 34 days he served in 1987 after smacking a film extra — an activity frowned upon by those monitoring Penn’s progress while he was on probation for clocking a guy who tried to kiss his then wife, Madonna.

It’s now early afternoon, and Penn is contemplating his legend thus far while he stretches out on a bed in the hotel room he has rented for the day. He munches from a box of Cracker Jacks, sets the unopened prize on a desk and speaks in a low, steady murmur.

“It took me some time to learn how to smell a problem and get the hell out of Dodge,” says Penn, 35. “But now I’ve been doing that pretty successfully for a long time. And I get a fair amount of privacy beyond what I would get because of the way people perceive my image.”

Penn mumbles a laugh and continues: “When we were filming Colors, Bob Duvall said to me: ‘I took this part because I get to kick your ass and throw you against a locker. Everybody in America wants to kick your ass and throw you against a locker. I’m gonna be a hero.”‘

There is no delicate way to put this, so it’s best just to come straight out with it: Penn is peeing in an empty wine bottle, a stone’s throw away from a small table where a few of Hollywood’s most upwardly mobile stars sit, watching intently.

Afternoon has given way to late night, the hotel bar is empty, Cracker Jacks have given way to vodka tonics, and Penn’s cautious, resonant whisper has been replaced with a folksy, easygoing drawl. Penn’s guests include the actors Ashley Judd, Josh Hamilton and Mira Sorvino. To hammer home the surreal nature of this gathering, both Judd and Sorvino, who have been shooting an HBO movie, are coifed as Marilyn Monroe. Penn, being the most accomplished of the assembled mass, presides over the gathering with panache. He recites jokes, he tells stories, he finishes urinating. Almost.

“I need another bottle,” says Penn.

He sets the brimming vessel in front of him, and the room erupts with laughter. He of the enormous bladder grins, and a second bottle is placed in his left hand before it quickly disappears under the tablecloth. . . . Relief.

There are many things that have brought us to this place, but the chief motivator — with all due respect to the vodka, which places a close second — is that Penn is an insomniac who lives in a 27 1/2-foot trailer and, as such, spends a great deal of time away from his residence. Granted, this doesn’t explain not making the 100-yard trek to the bathroom, but it does speak to the deeper issue of why Penn has rented a hotel room less than 20 miles from his primary billing address.

“I don’t consider that I have a home,” says Penn. “I’ve got two kids, and if I don’t have them with me, it doesn’t feel like I have a home. At one time I lived with a woman and two children in a house, and that was a home. When my kids are with me, I rent a house. That was part of the deal for me getting as many days with them. They love the trailer, but she says it’s better. She might be right, but the minute they walk out the door, I fall on my knees.”

The woman in question is actress Robin Wright; the children are Dylan, 4, and Hopper, 2. The couple have recently tossed the flowers on a relationship that Penn says died a number of years ago, and Penn, as is his wont, has tortured himself with the questions of what went wrong, how to be a good part-time father and whether the pain of the breakup will inspire the kind of craft he most admires.

You see, Penn is one of those guys and then some. Not only did Penn go through a Charles Bukowski phase, he went through Charles Bukowski, spending virtually every Sunday with the barfly writer, telling stories and drinking. Penn chain-smokes; he wears a lot of black; he does all his writing on an electric typewriter, preferring old-school affectation to the efficiency of a word processor. His Hollywood friends are mostly older art-through-experience types like Marlon Brando, and his other friends are mostly older writers cut from the very same cloth, typified by David Rabe and Cormac McCarthy: real men doing manly things with men in a masculine way. And while Rabe and McCarthy are men of remarkable artistic ability, they also embody an aesthetic and a lifestyle that do not come naturally to a movie star of some stature.

Asked whether owning 50 acres of Malibu, Calif., property (the home he once shared with Madonna burned down in the area’s fires in 1993) but choosing to dwell in a trailer isn’t potentially offensive to people who have to live that way out of necessity, Penn initially explodes: “Anybody poor who thinks I’m condescending can kiss my ass. Anybody rich who thinks I’m jerking them can kiss my ass, too. I like the coziness of a small place. I’m not going to defend my lifestyle.” But hours later, Penn brings up the topic again to amend his statement. “I’d never considered that that angle existed. I always figured you offended poor people if you drove a fucking Mercedes down Martin Luther King Boulevard. But it’s not my obligation to deal with that. I think I’ve been through enough that I honestly don’t give a fuck what anybody thinks about me except the people close to me. And the people close to me I probably give a shit too much.”

To speak with Penn is to become versed in a language that is part self-analysis, part philosophy and part barroom poetry, all without the benefit of a translator. At first he is guarded, attempting a type of silent intimidation, and later he is cordial, sincere and likable, albeit in a way that occasionally makes you feel there should be other men in the room banging drums and weeping.

“I came to a very analytical point in my life toward the end of that family situation,” says Penn. “And in order to look back on my life, I have to pass through the last seven years, and I’m not real happy about the past seven years of my life. I don’t feel like looking back on that period right now. It’ll have its day in court. I’ve been humbled plenty. My kids’ mother humbled me.”

Penn sips his drink quietly and pauses for a long time when asked why he refers to Madonna as “my ex-wife” and Robin Wright as “the mother of my kids.”

“I suppose if I used my own terms . . .” Penn stops and indulges in another lengthy pause. “I’ll leave it at that.” He sips his drink and waits a moment. “But I will tell you that I wasn’t going to a negative place.”

And with that, Penn once again resumes his more genial posture — reciting a joke in the voice of Brando, suggesting a number of books, displaying the tattoo that reads Nola Deliver Me, which he got to commemorate a frighteningly wild night in New Orleans (hence the NOLA) — but eventually he returns to a familiar theme.

“I’ll tell ya probably the most naked thing I could say in an interview,” says Penn, leaning forward in his chair. “I’m damaged. And I recognize that. But I have great faith in the resurrection of all beautiful things except innocence. Innocence is a constant, and damage to me is gauged by how far you’ve gotten away from innocence. I’ve learned in the last couple years about forgiving myself, but you might as well be speaking Greek if you tell me you have no regrets. I have very serious regrets. I’ve got regrets that don’t have statutes of limitations on them.”

The acreage that now houses Sean Penn’s one-man trailer park is well protected. So well protected, in fact, that Penn says he has made seven citizen’s arrests on the grounds during his tenure as tenant and sheriff.

“I near cut the ear off of one guy,” says Penn, perhaps too giddily. “I had excessive-force charges against me. I cut his ear with a broken salad-dressing bottle. He was one of five guys who broke in that I arrested one night when I had a house up there.” Penn laughs. “The property originally belonged to Olivia Newton-John, and I found one of her wackos looking for her — got him, put him in jail. He went crazy and beat up a guard. I get some wackos. I’m one canyon over from Topanga [Canyon], where the Manson family was. I’m a child of the ’60s; I remember that shit.”

Penn laughs again in a way that makes one wonder if at times his mental state might also be one canyon over from Topanga. While some people choose to pack heat, Penn chooses to stockpile for the apocalypse.

“Listen, we’ve got 382 functioning serial killers in the country who are at large,” he says. “So I’m not going to be up there with my kids without a gun. Locked up? Yeah. There’s combo boxes. I’ve gone through the Los Angeles Police Academy weapons training. I don’t have one gun that I’m not expert in. I have very mixed feelings about guns, but I’m extremely careful about them. I don’t have a love-hate relationship with guns. I have a caution-hate relationship.”

Meanwhile, things are getting cozy. The hotel bar has long since closed shop, but the Penn group is busy chasing the sunrise. Ashley Judd sneaked off to her room only to return with more booze and chewing tobacco (everyone indulges in the former; only she partakes of the latter), and Penn has turned a non-brooding cheek in order to charm the attentive round table. As testimony, Josh Hamilton politely waits his turn at storytelling, and Mira Sorvino takes off her shoes to rest her feet on Penn’s chair.

It is a far cry from my first two meetings with Penn, during which he shifted uncomfortably in his seat, answered every query with suspicion and spoke in a self-consciously throaty mumble only a note or two above a yawn. At this point, when the conversation is diverted from him for a moment, Penn is happy to tackle the topic of whether it was a strange sensation to have introduced his ex-wife to her next beau, Warren Beatty. Penn laughs and leans forward. “I sent him a letter,” says Penn. “It just said, ‘Dear Warren: Yuck, yuck.'” And then, Penn laughs again.

“Sean and I are very good friends, but he also has a lot of friends,” says David Morse, the star of The Indian Runner and The Crossing Guard, Penn’s two forays into both writing and directing. “His life exists spread across the entire globe. My world has much smaller parameters.”

In the beginning, Penn’s world was as confined as yours or mine. Penn was raised in California’s San Fernando Valley and Malibu; Penn’s mother, Eileen Ryan, is an actress (she played a grieving mother in The Indian Runner, had her finger sucked by Jack Nicholson in The Crossing Guard and portrayed Penn’s grandmother in At Close Range), and his father, Leo Penn, is a TV and movie director. Times, however, were sometimes difficult, because his father had been blacklisted as a Communist and had trouble getting work for years.

“Being blacklisted hit my father pretty hard in terms of momentum,” says Penn. “And my parents had my brother Michael to support. Luckily my mother could get some TV gigs. My father didn’t talk much about it, but I remember Elia Kazan was shooting a movie once on the beach at the bottom of our hill. I’d heard about Kazan because he had named names. And there he was at the bottom of our hill.” Penn stops and his whisper gets even softer. “Very strange.”

According to Penn, the greatest constant in his youth was the love and support of his parents, a fact that makes his breakup with Wright all the more poignant. “I’ve spent time with Sean and his family,” says Timothy Hutton, whose friendship with Penn began when they filmed Taps, Penn’s first movie, in 1981. “They’re a very solid family, and they also know how to get under each other’s skin. They’re very real with each other. Nobody gets away with anything when they’re around each other. It’s great.”

Which makes one wonder about the origins of Penn’s occasionally violent temper. Asked about its genesis, Penn stays silent for a long while. “The only consistent area of violence in my life was surfing,” he says finally. “I was a surfer on a beach that had a lot of heavy localism. If surfers from other areas came to our beach, it was not something that was allowed to happen; it’s your beach, and the people around you back your action. It was built into the culture. At least there’d be a lot of vandalism to automobiles.”

By high school, most of Penn’s nonsurfing time was spent with his younger brother, Chris, and their friend Emilio Estevez, making Super 8 movies while brother Michael holed up in a room and played guitar. Which makes sense, considering that Chris now acts, and Michael is a recording artist. Estevez, of course, went on to divorce Paula Abdul.

“My brothers grew up in the same house as me, and we’re all three extremely different,” says Penn. “Chris hides his mind. He’s a whip. And he’s a bighearted guy, a gentle giant. Michael is really quiet and sensitive, but he has a pretty good sense of humor. I mean, he’s not out telling jokes, but brother to brother, Michael rocks.”

Still, in terms of established careers, it was the middle Penn who was the first out of the gate. With performances in Taps, Fast Times at Ridgemont High and Bad Boys, Sean Penn was an immediate presence in film, garnering a best-of-his-generation tag that he has not lost. He was also something of a serial fiance, pledging allegiance first to Bruce Springsteen’s sister, Pam (“Bruce was on the East Coast, so I hardly knew him,” says Penn), then to Racing With the Moon co-star Elizabeth McGovern before settling on Madonna and a tabloid existence that accelerated with his allegedly firing a gun at a hovering helicopter during his wedding and that ended three and a half years later, when a SWAT team interrupted his breakfast in order to let his wife retrieve a few material possessions. “I had made a threat that I would literally cut her hair off,” says Penn. “She took it quite seriously. It was pretty dramatic.”

These days, Penn and Madonna are on terms that do not require police assistance, and he recently surprised his ex by presenting her with a Most Fashionable Artist prize at the VH1 Fashion and Music Awards. “Any effortless thing that I could do to bring a smile to her face, I’d do — I’m crazy about her,” says Penn, who refutes reports that Madonna was unhappy about her presenter by mentioning that the two went out for dinner with friends after the ceremony. Not that Penn has softened his view on the paparazzi that often got in the way of his flailing fists. The cameras stalk him still, on dates with singer Jewel Kilcher and, more recently, model Elle Macpherson.

“It’s deceptive to judge people by what you’ve read so far in this decade,” says Penn. “Things have changed. If I was 20 now, I’d be in jail for life. Hard Copy and Inside Edition didn’t exist during my marriage. Imagine. I’d be in jail for murder one.” Penn laughs. “This is your 20s — you’re trying to figure out who the fuck you are. I’d take two years of state time beginning tomorrow rather than trade places with Leonardo DiCaprio. This guy’s got the gift. And he’s also got a wild spirit — no doubt about it. Great talent, a great face. He will not be presently lonely.” Penn smirks. “I tell ya, if I — do my state time, I’d do it with him.” He snorts out another laugh. “I always joke with Brad Pitt that I’d rather it was him, but I”d have to make sure he had his long-haired look.”

Sean Penn to English Dictionary, Part I

Are you overly modest about your own acting abilities?

If anything, I think you can look at yourself as a total fucking phony. There’s a silliness inherent in what I do. Or at least a threat of it that you hope to keep at bay. And if you’re trying to live an authentic life, if you’re totally in love with someone and you go out and fuck someone else, how silly do you feel, how stupid are you, but mostly how totally inauthentic do you feel when you go home and say, “I had drinks with the boys,” when actually you stuck your rod in somebody’s slipped disc? You’re just a clown in your own lies, and there’s a little of that threatening me all the time.

Translation: No, I don’t believe so.

Sean Penn to English dictionary, Part 2

Is there any truth to the rumor that you wouldn’t get out of character on the set of “Fast Times at Ridgemont High”?

Well, hmm. I would say that there were things I had to hold on to to not lose track of where I was. Acting was a learned thing for me, and at that point in time, once I had gotten boundaries of what had to be accomplished, I wouldn’t say that I had the greatest amount of faith in my motor memory of them all. And that it behooved me to hang on to certain aspects.

Translation: Yes.

I would be very very surprised if I win, because it has always seemed like a certain type of club that I never felt allowed to enter.”

Penn stops pacing for a moment, perhaps searching for an answer. The question is whether he would accept the Oscar he deserves for his role in Dead Man Walking — the fact-based tale of a death-row inmate (Penn) and the nun (Susan Sarandon) who becomes his spiritual adviser — but Penn has been circling the question for the last few minutes.

“Which is not to say anything disparaging about it,” he says. “It just seems really foreign to me, and if you’re going to take people’s positive judgments, you better be willing to validate their negative judgments. I think everybody knows that the Academy Awards are really just an advertising campaign for moviedom.”

Penn sits down, satisfied with his evasion, and lights what must be his 77th cigarette. Finally, when the silence grows as thick as the smoke, he speaks again: “A lot of people have asked me that, but I just don’t know.”

It is a strange position for Penn to be in. Several years ago, when he wrote and directed The Indian Runner, Penn claimed that he had given up acting cold turkey. Then admitting that the responsibilities of having children and the desire to finance another movie made the payday his main motivation, he accepted a role in Carlito’s Way. Now, with Dead Man Walking, Penn insists that the script was simply too good to pass up, a decision that sat well with his director.

“I wanted the best actor I could find to play opposite Susan, and Sean was my first choice,” says Tim Robbins, who also adapted the screenplay from the book of the same name.”I think he’s the best actor of our generation. It was very simple. I had a conversation with him, he read the script, he said yes.”

Casting was crucial because the success of Dead Man Walking hangs purely on the balance of its two lead actors. At times less a film than a two-person play, it is an emotionally draining study of these two primary characters, and both Penn and Sarandon, who also was nominated for an Oscar, provide career performances. Penn’s work, in fact, becomes all the more incredible when you realize that he spends almost the entire film in shackles. “This movie was so well written that a lot more of my work than usual came straight out of the script,” says Penn. “Things that I used to have to work very hard to achieve are coming more second nature. I think that’s allowing me a little bit more simplicity if the writing is good. And in this case the writing was really good.” He stops. “And the other thing is that Susan Sarandon is the most present actress. She’s, like, the last American woman.”

What might surprise some is that Robbins — often as famous for the sheaf of colored ribbons attached to his public personae as he is for his acting and directing talents — has created a bleak but balanced look at capital punishment. Rather than being unjustly accused, Penn’s character is simply a sociopath — “I could just imagine the conversation with some other actors,” says Robbins. “‘Don’t you think this guy’s unsympathetic?'” — and moviegoers on both sides of the death-penalty debate could easily walk out of the theater feeling vindicated in their beliefs.

“This movie provokes a lot of thought, but I don’t think it surrenders to one side or the other,” says Penn. “I remember there was a lot of complaining about the movie Guilty by Suspicion. My father and a lot of the people who were blacklisted were offended that although the movie was sympathetic to the Communists in America who lost the ability to work, the lead character stood up for people’s freedom of belief but was not a Communist himself.”

Nonetheless, in his new incarnation as nouveau writer-director Beat-type guy, acting is something that Penn would rather not process at all. He is currently electrically typing a new screenplay and has already talked to David Morse about his possible involvement. Penn’s first efforts behind the camera have been received with promising but mixed reviews — The Indian Runner, poignant but slow; The Crossing Guard, a series of interesting ideas without adequate execution — but Penn sees himself as a writer and director who occasionally acts to pay the bills. To that end, he is about to shoot a film — The Bells of Hell — in which he plays the Irish playwright, rogue and renowned boozer Brendan Behan. His carrying on tonight is pure Behan.

“The good news for the rest of us is that the types of films he wants to make are the kind that will find their way into smaller theaters,” says Morse. “So in order to be able to do that, he will need to keep acting occasionally. He’s such a courageous actor, and the chances and the choices he makes are incredible.”

And, who knows, both fatherhood and directing might have softened Penn up a bit. At least to the extent that he now plays well with others.

“I didn’t find him far removed from us at all,” says Robbins. “From the first day he laughed, he joked. In between takes, he’d break character. I’d heard stories about him, but they were totally unfounded — that bullshit about having to refer to him as his character’s name. That stuff usually comes from a source that has a personal vengeance involved. I asked him about it, and it came from a particular director or producer who he’d gotten into a difficult situation with. Total bullshit.”

Now you’re gonna hear the story because I’ve had a couple vodka tonics.” Penn smiles and adopts a less-than-professorial tone. “Here’s the one rule for any young actor in Hollywood: If she has a picture of Marilyn Monroe in her powder room, you’re gonna get laid. You know the trouble is getting serious in a relationship when you’re forced to read The Road Less Traveled for the 88th time. And then you’re going to put up with two psychotherapy sessions until your confidence builds enough for you to say, ‘Fuck you, I’m not going again.’ Which, in the end, will fuck you.”

Penn pauses and leans back in his chair. “Nothing will rejuvenate you like vodka, I’ll tell you that,” he says. “My early 20s were engaged in the ambers.” He stops and falls contentedly silent. Here endeth the lesson.

Penn freely admits that he is not a morning person. Therefore it’s a pretty safe bet that this moment belongs not to the new day but to the previous night. It’s 6 a.m., and despite the fact that the sun also rises, the evening lingers on. It might not be the freshest crowd — Judd and Sorvino are beginning to look less like the Marilyn Monroe of Some Like It Hot and more like the Monroe of The Misfits — but all in all, it’s a pretty strong performance by the new kids. Especially considering that Penn often seems intent on chasing a legacy that would make Hemingway feel like a pantywaist.

We consult an expert. “I’ve definitely experienced a few of those nights over 15 years,” says Hutton, who then goes silent. But isn’t Penn a split personality of old-school ethics and pure Hollywood carousing? “Yeah, definitely.” Hutton clams up again. So which one is more prevalent? “Both sides exist. Neither is more prevalent. Especially since Sean has become a father, I’ve noticed that if he has something he wants to put down on paper, he’ll stay with that until it’s down. It doesn’t matter how many calls he gets to go out.”

And thus it is part of the Sean Penn conundrum that his artistic sensibilities often overlap with a more basic boys-will-be-boys attitude. Penn clearly views himself as a kind of literary desperado — “There’s just a pursuit of excellence that I respond to,” he says — and he’s comfortable knowing that outlaws such as himself might piss in a few wine bottles and toast a few sunrises. Then again, sometimes frat boys do the same damn things.

So in order to understand Penn, it is important to grasp his contradictions. It’s highly unlikely that the discrepancies escape him. Ask him what he romanticizes, and Penn grows flowery. “I romanticize love,” he says. “I think everybody deserves adoration.” Ask him if he doesn’t also romanticize the rebel image typified by his stints in jail, and he grows defensive. “I’ve been in several jails here and there. When I spent the longest time, there was so much stress in my life at the time that if I was able to romanticize it somehow, it would be the relief I remember now. I sat in that cell day after day not knowing whether to laugh or cry. I just kept thinking, ‘This is jail. Am I really a threat to society?”‘ But ask him to list both his best and worst character traits, and he shoots from the hip immediately with just one sentence: “I tell the truth.”

Listen to his friends. “Sean has a great loyalty that really knows no bounds,” says Morse. “The only bounds being maybe dishonesty.” Hutton agrees. “He’s very honest and very loyal,” Hutton says. “You get the sense with Sean that friendship is a lifetime thing.” And Robbins: “One word that I would say is real key to understanding Sean is honesty.”

So here sits Honest Sean, cigarette in hand, a bit liquored up, the morning breaking through the window. He has grown more comfortable as the interview has gone along, but he has also taken great pains to let you know that his cards are never far from his leather-jacketed chest.

“What is a pain in the ass is what you can’t express because of the emotional politics of your personal life,” says Penn. “All of the sudden you’re offered this opportunity to express things in a way that will get to the people you want it to, and you know it’s improper conduct.” He pauses. “It also bothers me that every time you do an interview, you are propagating the notion that you are special. I’m always reluctant about that. It’s the only thing that bothers me about being recognized.”

That is what bothers Penn. Not his cowboy image, not the series of scars that hint at a less-than-perfect barroom-fighting record, not that he eats his home dinners outdoors because he happens to live in a trailer. No, what bothers Penn is that people will think — because he stars in movies — that he is a movie star. Penn scrunches his angular face to let you know he is about to express a pained, heartfelt thought.

“The way I’ve chosen to do things is almost because it’s the only way I can have any confirmation that there’s something important about this kind of work,” he says. “This is the only way I can look in the mirror.”

Penn sips his drink and smiles, content that in a short time he will walk one flight of stairs to his rented room, close the curtains on the impending day and face himself in the mirror, bleary-eyed but exactly the same. 

In This Article: Coverwall, Sean Penn

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