Let fury have the hour, anger can be power

D’you know that you can use it?

—The Clash, “Clampdown”

The drive from Oakland to Mill Valley sends you across the Richmond/San Rafael Bridge, worth the $4 toll for its breathtaking views of Mount Tamalpais, the sentinel of Marin County, and the gilded burgs over which it watches. Near the end of the bridge is another landmark: San Quentin State Prison, a place that teases the hard cases locked in there with a panorama of Mt. Tam that from the prison yard feels so close you’d think you could reach out and touch it. I don’t know if that’s irony or cruelty, but I do know prisons are sure given prime real estate in these parts. One of Sean Penn’s best friends is stuck there in San Quentin, maybe for good, and Penn cites this unfortunate fact as one of his main reasons for choosing to live in this corner of Marin County. He simply wanted to be closer to his friend.

I don’t think Penn cared much about being closer to the Acqua Hotel in Mill Valley, where we are to meet, a place that looks like it was dreamed up by a set designer for the James Bond franchise. Even with its backside views of a San Francisco Bay inlet and its sun-splashed interior, the Acqua feels sterile, its elegance — all clean surfaces, unmolested bright walls, lots of light and sharp lines — contrived. It’s tragically hip, and it seems like an odd place to be meeting Sean Penn. It’s more like a place one of his characters would inhabit, like the bright and soulless loft Jack Nicholson’s bereft Freddy Gale retreats to for booze and bad sex in The Crossing Guard.

When Sammy Hagar, the man who achieved the impossible by killing Van Halen, pulls up in a black Maserati and emerges wearing extra-long shorts, bad footwear and a T-shirt promoting some bunk product or event, and is urgently greeted by a severe blond publicist type straight out of central casting, the whole thing starts to feel absurd. I poke my cigarette into the air, thinking some dimension will surely burst. It doesn’t.

Actually, it does. About 15 minutes later, when . . . well, picture if you will a sleepless and forlorn journalist chain smoking in front of the all-glass doors of the David Lynchian Acqua Hotel. A plume of smoke fills the foreground just as a beater of a Land Rover rambles into the parking lot a little too fast and all but crashes into a tight parking space. As the smoke dissipates, Sean Penn tumbles out of the Land Rover in worn work boots, jeans and a gray T-shirt. He approaches with the athletic grace of a cat, all body parts in motion at once. He’s muscular like a construction worker. His hair is wild and magnificent, and there are deep crags around his cowboy eyes. The first words out of his mouth are:

“Can I bum one of your cigarettes? I’m sorry, I left mine back at the house.”

“No, problem,” you say, and then, for no good reason, or because you have no impulse control: “I’m getting divorced.”

“Shit,” he says, exhaling and looking you in the eye. “I’m sorry about that. That’s a bear.”

Sammy Hagar should watch that entrance in slow motion, repeatedly.

I’m up here interviewing Penn because a film he wrote and directed is imminent. But instead of settling into a hotel couch for the standard grilling, we finish our cigarettes and Penn suggests we take quick leave of the Acqua. He spent the previous day — beginning at 5 a.m. and ending at 6 p.m. — rafting the North Fork of the American River and is still hungry and a bit worn out. We head for a local sushi joint in a civilized Marin County commercial center that would be a strip mall anyplace else. On the way there, Penn drives in a manner I’d describe as intent but not overly aggressive. I study the ink on his arms, which I noticed immediately upon greeting. It’s authentic old-school work, almost of the prison variety, and a refreshing contrast to the rote tribal decorations that have become de rigueur for frat boys and young Hollywood alike. (Is there a difference?)

Penn’s new movie, Into the Wild, based on the Jon Krakauer book of the same name, tracks the journey of a young man away from the conventions of his birthright and into a deep, deep wilderness that is both literal and ontological. It’s an epic and ultimately fatal quest, one that Penn has rendered onto screen in ways that feel more relatable and intimate than Krakauer’s account, which, as a mostly journalistic undertaking, couldn’t help but keep its protagonist at a short arm’s length. I read the book and saw the film, but it was the film that made me feel like I got to know Chris McCandless. It’s touching and heartbreaking and infinitely more accessible than Penn’s previous efforts as the writer and director of such dark and troubling ruminations as The Indian Runner and The Crossing Guard, and as director of The Pledge.


Penn began pursing Into the Wild almost immediately after the book came out in 1996. Securing the rights was no easy task; a family and all the legacy they have left of their son were at stake. After reading the book, Penn found out a lot of Hollywood folks were trying to nail it down. He got in touch with Krakauer’s agent, who got him in touch with the McCandless family — father Walt, mother Billie and Chris’ sister, Corine.

“Jon flew to Virginia and I flew to Virginia, and we all met there,” Penn says. “After two meetings they had mutually decided on me. I was going to do a third kind of close-the-deal session, and I was leaving [for the airport] at 5 in the morning and I went to the shower. I got a call and Robin [Wright Penn, his wife] got me out of the shower and it was Billie, the mother. She had a dream that Chris did not want the movie made. ‘Do not get on the plane.’

“So, I didn’t. And I remember repeating this, because it was the truth — I said to her that if I didn’t believe in dreams, I would not make movies. So I left it at that.”

Penn stayed in touch with the family over the years. When he was in New Orleans last year filming All the King’s Men, he got a call from the family’s representative asking if he was still interested in making the film.

“That was a decade later,” Penn says.

This film, and the book before it, contains a subplot to the narrative of Chris McCandless’ journey — one of family secrets and dysfunctions, many of which fueled the young man’s uncompromising and, in the end, lethal ideology or idealism (you decide). That families have secrets and dysfunctions a young man or woman might struggle to come to terms with is no revelation. What is a revelation, though, is the courage the McCandless family shows in turning its dark underside toward the light so that we may learn whatever we will from Chris’ tale. That exposure is particularly raw and unabashed in the film.

“It is tougher in the movie,” Penn agrees. “It is something, you know — they struggled with it. I know. But I felt, it is my speculation, that there is a degree of penance involved in their decision, and I think it is a brave and selfless decision. But they struggle with it still. They go in and out, and I just got very good news that they are coming to the L.A. premiere, which really makes me happy. I’m just grateful to them for seeing it through . . . revisiting it in such a loud and public way.”

This film means a lot to Penn. Not just because he wants to repay the trust given him by the McCandless family and by Jon Krakauer, which he does, but also because well into a career as one of the most, if not the most respected actor of his generation — though one who can’t guarantee box office — and after directing three well-regarded movies that never quite transcended cult status, Penn would like to know somebody’s out there.

“I really want a lot of people to see it,” he tells me. “I want it to mean something to people. I am going to feel that I have exercised my last piece of language in finding out if I am completely alone in this world or not if it is not responded to. So I’ve got some investment on that level.”

Penn tells me this near the end of our time together, a time during which we will smoke a pack of cigarettes, shoot pool and talk about everything from the role of language in civil society, to the importance of rites of passage, to what it means to be a citizen. Look, I know what you’re thinking, because everyone is immediately thinking something about Sean Penn. But I want to tell you: I think you’ll be surprised.

I’m going to be honest with you about where I’m going with this: I like this guy already. A lot. He had me before we even met, when last spring he made a speech in which he called Dick Cheney and Condoleezza Rice “villainously and criminally obscene people, obscene human beings, incompetent to fulfill your own self-serving agenda, while tragically neglectful and destructive of ours and our country’s.”


Actually, he had me way before that (but I really like that one), back when the initial Iraq war drums were beating and anyone with an ounce of intelligence and insight could predict the looming disaster that has since unfolded beyond our worst imaginations. Penn was one of the first Hollywood voices to speak out. On October 19, 2002, he published an open letter to President Bush in TheWashington Post lamenting his “simplistic and inflammatory view of good and evil.” And he called out the lapdog media that has been complicit in this calamity: “Take a close look at your most vehement media supporter. See the fear in their eyes as their loud voices of support ring out with that historically disastrous undercurrent of rage and panic masked as ‘straight, tough talk.’ ”

Penn’s opposition to this regime has been uncensored and unrelentingly memorable ever since, whether it’s fishing old people out of flooded New Orleans — something for which he earned wide criticism as a PR hound, despite the insistence of New Orleans historian and author Douglas Brinkley that his efforts were genuine and responsible for saving 40 or so people — or writing (quite well) about his experiences in Iraq and Iran, visiting with Venezuelan President Hugo Chavez, or posting his frequent tirades against this administration’s chronic criminality. For me, his protests exist somewhere between metaphor and metaphysics. And I’m all for it. But it seems to make a lot of people uncomfortable, as if metaphors actually exist that are too strong for declaiming the calamities of the Bush era.

One of Penn’s more priceless moments came during a speech he delivered at a town meeting held last March by Democratic Congresswoman Barbara Lee, who represents much of the East Bay. Addressing the president, Penn said, “We cower as you point your fingers telling us to support our troops. You and the smarmy pundits in your pocket — those who bathe in the moisture of your soiled and blood-soaked underwear — can take that noise and shove it.”

Forget whether you agree with him or not (and how couldn’t you?), how about a little appreciation for the sheer poetry of it? That speech, and those lines in particular, earned him a rare moment of comic relief on The Colbert Report, during which he and Stephen Colbert engaged in a Meta-Free-Phor-All judged by former poet laureate Robert Pinksy. Penn won the contest 10,000 points to 1 by working the soiled-and-blood-soaked imagery into every metaphor, whether the category was world leaders or love. (“Love is a fragile flower opening to the first warmth of spring whose crimson petals are not as red as George Bush’s soiled and blood-soaked underwear.”)

The bit was hilarious and has become an Internet favorite. But the line was actually a late addition to his speech. “I was on the freeway, kind of going over the speech in my head, and I just started thinking about those guys and I got angrier and angrier. I pulled over on the side of the road and that was the last thing I added to it.”

The Penn of The Colbert Report, the self-deprecating one, seems genuine. As I see him today, he appears to be a far cry from Jimmy Markum, the vengeful father he won an Oscar for playing in Mystic River, or the popular caricature of a thuggish celeb out to bash any hapless paparazzo who gets in his way. He’s engaging, thoughtful and, despite a physical presence that suggests a coiled cobra, gentle. We take a table in the back of the restaurant and order a modest amount of sushi and talk while chewing. The staff here seems to know him, and he treats everyone courteously.

In a way, TheColbert Report send-up was perfect because the show operates as a parody of the phony journalism we’re fed from so many sources, including major networks. Penn himself is a sharp amateur journalist. He has traveled to Iraq twice since the war began and written about both experiences for the San Francisco Chronicle. His second account, from a January 2004 visit, contains this caveat about the challenges he faced selling the trip to his family: “My reputation within our own home is one of impulsiveness, hubris and an overall bloated sense of my own survival instincts. Of course, this is entirely unfounded, but we’ll leave that for another day.”

The reports are well observed and nonpolemical, rich in detail. One observation proved particularly astute: “It is a compelling experience to have been in Baghdad just one year ago, where not a single Iraqi expressed to me opinions outside the Baathist party lines, and just one year later, when so many express their opinions and so many opinions compete for attention. Where the debate is similar to that in the United States is over the way in which the business of war will administer the opportunity for peace and freedom, and the reasonable expectation of Iraqi self-rule.”


While reading his accounts, it occurred to me that Penn has an abiding respect for the practice of journalism.

“Yes, you know, if there is going to be a turn,” he tells me, “it is going to come out of that.”

I ask if he’s disappointed in the level of journalism that’s been practiced over the past several years.

“I’m disappointed in actors who become models and journalists who become contest-show hosts,” he says. “I feel what disappoints me the most is somebody who can do something well and does not do it. The people kind of letting the culture lead them instead of leading the culture. I mean, freedom of speech exists in North Korea — if you trust your wife. But where it counts is with journalists . . . I mean, it’s not the domain of journalists, is the problem. It’s the domain of all of us, but where I worry about it the most is in journalism.”

Penn, of course, received a ration of shit for his much-publicized recent visit to Venezuela as Hugo Chavez’s guest. He won’t talk about it now because he’s writing a piece on it, except to say “it was a fascinating trip” and that things there, including the press clampdown, aren’t quite what we’re led to believe. Why, many have asked, would Penn play guest to Hugo Chavez and risk being seen as naif? I believe the answer is that he is not a proponent of received knowledge. Take Chris McCandless’ sojourn, for example. Even though it was well documented in the Krakauer book, Penn took it upon himself in researching his screenplay to retrace much of McCandless’ path. He spent time in the Anza-Borrego Desert, visited seminal characters in McCandless’ life, and even made a somewhat harrowing trip to the Alaskan wilds, where he crossed, with Krakauer, the river that penned McCandless in when he’d finally had enough and wanted to return to civilization — a river that, as much as anything, played a fatal role in the young man’s story. The through line, though, whether it be post-deluge New Orleans or post-invasion Iraq, is that Penn is going to see for himself.

He makes this clear to me when I suggest that his public tirades, and such indelible images as him rowing a boat through the streets of New Orleans, plucking people from the flood, are a form of political theater.

“I’m not that smart,” he says. “I have noticed some things have happened that are working that way, or firing that way. But no, I’m a guy who watches a little television, gets pissed off and decides I am pissed off because I don’t know enough about it to make a good argument. But my gut knows they are full of shit, and then I go out and force myself to learn by getting in the middle of it.”

When did Penn the actor become Penn the political animal? It would be easy to blame George Bush, if blame is what you’d like to do. But Penn cautions against such an easy read. He tells me he’d been politically active for a while before the Bush presidency but felt it better to maintain some separation between politics and art. That changed when he had kids.

“I grew up in a politically engaged family. My father [actor and director Leo Penn] was blacklisted, and he was a very strong, patriotic guy nonetheless,” he says. “I felt that in lieu of the silence of what was going on in my field at that time, particularly related to the Iraq war that was about to happen, that I was not going to go to bed proud just on the faith of what good work I do politically anymore, because I did not think we had time for that. And I am still not sure we have time.”

There is, of course, silence, and then there’s what Penn does. His public denouncements are saturated with a rage that frightens some, while others witness these performances and think, Fuck yeah, I’ll take another dish of that. But there is something more than urgency feeding his swing-for-the-fences activism — something internal.

“I think you got to go with where your voice comes from,” Penn tells me as softly as the breeze is coming off the Bay on this post-card day. He exhales a large plume of smoke (we’ve moved outside by now so we can take minutes off our lives unfettered) and adds, “I have largely been fueled on anger. There is no question about it.”


I ask where that anger comes from.

“I am one of these people who went through a series of demon doors of my own creation. It was just like, I mean the only thing I can think of is that I have put much of it in TheIndian Runner, you know, where there is a generation of us that grew up every day as my kids are today — but we had real coverage of the Vietnam War. It was real. It was my neighbors’ older brothers and shit. I love that fucking Mustang, or maybe it was a Firebird, that is now up on the blocks in the garage of my buddy’s house because his brother, whose car it was, had to drain all the oil before he went overseas and then he comes back dead and I am seeing things that are related on television. I was growing up in the Valley at that time, and we had six or eight kids on our street that went off and were killed, and they were not kids to me at the time. They were adults to me, but they were the coolest adults on the planet because we were all about go-carts and motorcycles, and we were younger. They were just these cool guys, and they were all slaughtered.”

So, are you suggesting that anger can be power?

“Yes, but you can’t live alone,” he says. “There has to be balance. I could see an idealistic movement, if it just had a lot of people agreeing to go with it. Dennis Kucinich will be president. All we have to do is vote for him.

“You know, I am shamefully Johnny-come-lately to it, in a way, but once you’ve stepped into the arena, my own experience is there’s no going back.”

Sean Penn’s family moved from the Valley to out near Point Dume when he was still a kid. It was the country part of Malibu back then, and he says he had a “Huck Finn kind of existence with surfing” growing up. Penn says he can handle eight-to-10-foot Pipeline on a good day if it isn’t too crowded.

“I am comfortable in 10-foot surf in most places,” he tells me. “After that, I watch from the beach.”

I tell him that five-foot is about my cutoff.

“Well, that’s the best, the most fun, three-to-five-foot perfect waves. My favorite place still today in the world is the Ranch.”

The Ranch is the legendary surf spot north of Santa Barbara on untrammeled, privately held land. It’s one of the most beautiful areas in the world. I have been fortunate enough to have surfed it with Dana Brown, son of Bruce Brown, the man responsible for Endless Summer. Dana himself directed the wonderful Step Into Liquid a few years back. It was at the Ranch where Penn made one of his most significant discoveries.

“I had my 14th birthday there in a tent for four days with a buddy of mine,” he tells me. “There are two things that happened. I fell in love with the Ranch, but the other thing is, I fell in love with mustard. You know how you get a hunger like nothing else when you’re surfing? Well, we had run out of our food supply pretty fast down there. One night, we were surfing Rights and Lefts [surf breaks]. We camped right in front of Utah’s just down the beach, and some guys were camped down the beach and they’re making hot dogs. I always hated mustard. So, they go, ‘You want some hot dogs?’ We came running up there and they had already put mustard on it, and I was like, ‘No, no, no!’ But I was so hungry I ate one anyway and then I was like, ‘Aahhhh.’ Ever since then, I ate a lot of mustard.”

For some reason, though, it seems like there’s always a dark side looming on the edge of Southern California paradise, and it soon began to envelop the beach culture Penn grew up around. By the ’70s, Mike Hynson, the golden-boy star of Endless Summer, was battling with substance abuse, running afoul of the law and even ending up on Nixon’s enemies list. Miki Dora, the dark prince of Malibu, was off on his outlaw escapades. A lot of Penn’s friends became casualties.

“They found a reason to get into so much trouble and kill themselves and kill others,” Penn says. “It was the weirdest thing. One of my best friends from that time, whenever we got drunk, that is all we’d talk about. It’s all those guys that are gone.”

I ask if it was just the times, or something else.

“Well, four out of five of the things were drug related, if not drug overdoses. It was criminality based on drugs, mostly,” he says. “Yeah, it was the times.”


Penn was lucky enough to have escaped to New York at age 17 to pursue theater and get on the path he is still on.

“The other stuff happened as we were becoming adults. My life moved away, so that stuff happened later to those guys. It was not part of my life. But those years, certainly, that I had were mostly positive. It was a rite-of-passage period. It was colorful at the time.”

Rites of passage are important to Penn, not in a facile, symbolic sense, but in the way that men and women test themselves and their boundaries to find a better sense of themselves and the truths and principles by which they are going to live their lives. It’s a theme that runs through all the films he’s written and/or directed, and it’s what drew him to the plight of Chris McCandless, a young man who, if nothing else, was searching for a code by which to live.

“The sense of traditional rites of passage are gone in our male culture, and I think increasingly there’s a hunger for it in our female culture as well,” he tells me. “And so there is not a rite of passage unless you create one for yourself. You never make that next step.”

And we become stuck in an infantile culture?

“Yes, exactly,” Penn says. “So the child-man who is also an economic slave goes home exhausted. He has worked his second shift in a day. His wife is now doing her shift, or something. The kids are screaming in the other room and he would rather watch Bill O’Reilly criticize Paris Hilton than think about something. It’s self-perpetuating. So I think with Chris McCandless, it was a young person taking advantage of his own wisdom, because young people still have that available.”

It seems clear that we’re going to have to make a move soon because I’m almost out of cigarettes, and these are the types of talks that cigarettes were made for.

“I am now returning to the philosophies I had when I was 17 or 18 years old,” he continues. “That is when I knew, and I was militant about it. The militancy is what makes you leave them, because that is wrong — you’re a fundamentalist-idealist and you are bulletproof. When you are real and combine that philosophy with some humility, which comes with being 47 years old . . . I become a more mature version of [that 17- or 18-year-old], and here is how: The rite of passage is humility, one way or another. The biggest strengths in things that ever happened to me were humiliations, and humiliation is a term we always use as a bad thing. It is not a bad thing, and it contains the word, humility. You add humility to that kind of idealism. Then you put tolerance with idealism and it makes you interested, and that is what leads to other things that are good things.”

I ask Penn, a man who saw his father and brother die too soon, and who has had his share of public struggles with the delicate art of growing up, what he considers to be his own rites of passage.

“Well, in my case, I’d say the closest thing to a catharsis was having children. My rites of passage when I was a young man were in the water. It is not the only way to do it, but it is the way that I found myself doing it that related to Chris McCandless, not in such a long-term sort of spiritual search, but definitely the most life-changing things were the times when I put my life on the edge. I don’t think it’s because of the life on the edge, literally. I think it’s because of the humility that comes with dancing with something that shows itself to be clearly bigger than you are.”

I tell him that I had that experience not long ago when I had to be pulled from the water by a 17-year-old girl.

“Hey, you know,” he laughs, “salvation comes in small packages. Surprising packages.”

Penn’s main muse is language. And his love of language is evident in the journalism he’s practiced — the attention to details, the facility with structure — but even more so in the films he’s written and directed. The Indian Runner, The Crossing Guard and Into the Wild (and also The Pledge, which he directed and which, like Into the Wild, was adapted from a book) — watching those films, the thing that struck me the most was that they were first and foremost written works, an element much of modern filmmaking lacks.


He cites movies like His Girl Friday and A Streetcar Named Desire, even with its atmosphere of working-class melodrama, as examples of an era when language reigned supreme in filmmaking and our movie-watching experience was the richer for it. Penn tells me his literary heroes are Steinbeck, Saroyan, McCarthy, García Márquez, Dostoyevsky, Ford (“Oh, and Krakauer,” he adds, laughing), and that it is in the tradition of language that we may find some measure of hope and salvation.

“With more access to language with television and now the Internet and everything else, the kind of lazy speech between friends is what people are now doing formally,” Penn explains. “This is how we talk, and those abbreviations are part of the culture. There is no culture in the language of the culture.”

He asks me if I have ever read George Washington’s Rules of Civility, and it isn’t a rhetorical question.

No, I confess.

“He wrote that when he was about 13 years old. It is shocking,” says Penn. “Television, computers, radio, what else do you have? Name it — the industrial revolution, the technological revolution and all this stuff and a 13-year-old without any of that wrote Rules of Civility. Dostoyevsky wrote Crime and Punishment without any of that. You know, without any of that. That stuff is not the answer. I think tradition is part of the answer.

“But we do not even value language when we talk to each other anymore — this is where tradition matters. It is our best song that we can sing for each other. So, if all we are going to sing is da, da, da . . . da, da, da . . . then there is no dancing in the culture, because there is no dancing in the language,” he continues, and given the levels of nicotine that are coursing through our neuroreceptors, I’m not about to stop him. “And so, the thing that I miss in my life more than anything — and by the way, I feel markedly guilty of it myself — is that we do not walk out the door in the morning with a culture that has a traditionally steep value of language.”

I ask Penn if he sees himself primarily as a writer, a hunch I’d come to while watching his films.

“Yeah, I think that’s most of what it is,” he says.

“Did you ever write a novel?” I ask, on another hunch.

“I played with one, got pretty far into it, and it burned up in this fire. At that time, I still wasn’t able to use a computer and I was just typing on an old typewriter. I had all the pages stacked up on my desk and it burned right on down. It was very nuanced, and the language of it is not something I could try to repeat. I’ve played with a couple ideas that I think I will eventually try.”

“You’re a good writer,” I say.

“Oh, thanks. I like doing it. I like when I catch a wave.”

When we’re perilously close to the end of my smokes, Penn takes me to his house later in the afternoon. It’s up a few windy, tree-lined roads in a burg that is upscale in that tasteful mid–Marin County way. Think Brentwood sans the ostentation. On the way over, Penn fields a few calls and gives me some advice about my pending divorce. It is mostly of the try-to-be-a-gentleman-and-don’t-succumb-to-the-temptation-to-blame-yourself sort. Oh, and get some Ambien. Nothing revelatory, but I appreciate the tone, heartfelt and free of empty platitudes. Standing out among the nondescript family trucksters in Penn’s driveway are a Porsche and a Ford Shelby GT500, if I’m not mistaken.

“That’s my baby,” Penn grins mischievously, as we pass by the Shelby. A perfect quarter-pipe for skateboarding sits in the middle of what was once intended to be a basketball or tennis court.

His house is beautiful, of course, tastefully decorated in an elegant country style. When we enter, his teenage son walks by, a blur of blond hair and limbs, already bigger than anyone else in the house. From somewhere in the deep interior, I hear the disembodied voice of Penn’s wife, Robin Wright Penn, shouting instructions as to where Penn might find the keys to one of his cars. It all seems so normal.

Penn is eager to show me the editing house where he cut Into the Wild, which is on the second level. It looks like a really elaborate home-entertainment center to me. Of more interest is the pool table in the back of the room.

“Wanna shoot a game?” I ask.

Thankfully, Penn has a pack of American Spirits nearby. We light up and I break, sinking a high ball. I make a couple more shots. Penn raises that one eyebrow in the way he’s famous for and squints through his cigarette smoke. He misses. We talk about the beauty of Eddie Vedder, who did a gorgeous soundtrack for Into the Wild (“I love that guy,” says Penn), and the decision to cast Emile Hirsch as Chris McCandless. Hirsch caught Penn’s eye in The Lords of Dogtown, for which he played the seminal skate punk, Jay Adams.


“It was right in my era, and I knew those guys peripherally and everything at the time,” says Penn. “It felt pretty genuine to me.”

Despite the spiritual and intellectual quest that was at the core of McCandless’ restlessness, playing him would require someone capable of such Herculean physical tests as running rapids in a canoe, hiking brutal desert climates, packing into the Alaskan wilderness and basically shedding an amount of weight that would give as adept a weight-loser as Christian Bale pause.

“We met. I knew Emile could act the part, I got that feeling pretty fast, but I did not know if he could act it for eight months under the conditions that we were going to be facing,” says Penn. “And he was amazing. He really had to live a monkey’s life for the eight months.”

I make a couple more shots and Penn jokes about me being a pool sharp. He sinks a couple and then I finish off the table, save the eight ball, which is stuck near the corner pocket behind one of the many, many balls he has left on the table. I take a gamble and jump his ball, miss mine, and scratch the cue ball. Penn wins.

“That was great,” he laughs. “Perfect.”

No, I say, that was a lesson in humility.

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