Activist Sean Penn

Citizen Penn – by John Lahr
Having traded braining the paparazzi for baiting President George W Bush, these days Sean Penn is almost as famous for his activism as his acting. In this definitive portrait, John Lahr hears from his family, friends, fellow actors and directors, and charts Penn's progress from Madonna to the mujahideen

In San Francisco one day last June, at 7.45am, an hour when even the pan handlers on Geary Street were still asleep, Sean Penn was standing in front of me, in sneakers, grey chinos and denim work shirt, his brown quiff catching glints of sun, alert and ready to go. 'I'm not so much an early riser as a non-sleeper,' he said, peering over his sunglasses. The day before, Penn had flown back from Tehran - where, as a correspondent for the San Francisco Chronicle, he had been covering the run-up to the Iranian elections - in order to attend the junior high-school graduation of his 15-year-old daughter, Dylan. This morning, he had dropped his 12-year-old son, Hopper, at school. Now, we headed off to San Francisco's Union Square, for some of Sears Fine Food's Swedish pancakes.

Penn, who is 45 and a compact 5ft 8in, is at ease in his body. There is nothing hunched or furtive in his bearing - he emanates what in earlier times would have been called 'backbone'. 'The feeling you get about him is that you can't call his bluff, because he's not bluffing,' Woody Allen said about Penn, who starred in his 1999 film Sweet and Lowdown. At the same time, Penn has a very specific gravity: reserve is part of his strength and his seduction. He is warm but no hail-fellow, polite but without that come-hither thing. 'You see me from 10ft away, everyone thinks I'm gonna bite or something,' Penn said. On first meeting, he gave no semaphore of greeting - no handshake, no smile, no small talk. His presence was his hello.

Over breakfast, he handed me an Iranian candy. He was preparing to write a 12,000-word article about his trip, which ran in the Chronicle in five instalments. He had a tantalising array of incidents from which to draw: he had attended prayers at a Tehran mosque, a women's rights demonstration, meetings with dissidents, a photo op with former president (and then presidential candidate) Ali Akbar Hashemi Rafsanjani, and, perhaps inevitably, an award ceremony for his acting, at the Film Museum of Iran. On his travels, he told me, he had been 'very aware of the ugly American', particularly among the reporters. 'There's a consistent insensitivity,' he said. 'I watched journalists. They could only ever be seen by their subject as the person with a deadline. It's "breaking news", literally. By the time you get the news, you've broken it. You don't get a chance to investigate stories. These journalists live half the time in the internet cafe, filing a story.' Penn described his own form of reportage as 'tournalism'. 'It's not an obligation of the tourist to observe experience so much as to have it,' he said. 'For me, a greater accuracy of perception comes out of that.'

A veteran of some 35 films, Penn is renowned, in the acting profession for the meticulousness of his research. 'Sean is a guy who doesn't want to analyse a character too much,' Alejandro Gonzalez Inarritu, who directed Penn in 21 Grams (2003), has said. 'He wants to be as the character.' For his portrait of the stoned surfer Jeff Spicoli, in Fast Times at Ridgemont High (1982) - the role that made him famous, at the age of 22 - Penn lived out of his car at the beach; to play a cop, in Colors (1988), he apprenticed to an LAPD officer; for the role of Emmet Ray, 'the world's second-greatest guitar player,' in Sweet and Lowdown, he studied guitar fingering. In his forays into politics and journalism, Penn relies on the same strategy. 'Sean's an investigative reporter of his emotional life and our world,' Dennis Hopper, who directed Penn in Colors, told me. 'Sean goes to the middle of the hurricane. He's not taking a second-hand opinion. He really wants to know what's going down.' In 1992, during the Rodney King riots in Los Angeles, Penn drove into the pandemonium and got a shopping trolley thrown through his windshield. In 2002 and 2003, he travelled to Iraq (once before the American-led invasion and once after), in order to observe life there - and, on the second visit, to write about it for the Chronicle. 'My trip is to personally record the human face of the Iraqi people so that their blood - along with that of American soldiers - would not be invisible on my own hands,' he said at a Baghdad press conference in 2002. In Penn's opinion, his shift from actor to correspondent was 'seamless'. 'You wake up in the morning with an interest in listening and expressing,' he said. 'It all feels the same to me. Acting is everyman-ness, and loving everyman. Finally, you're reaching out to people's pain.'

Because of his activism, Penn is often caricatured as a showboating celebrity liberal. 'It's as if Ernest Hemingway made sweet, sweet love to Jeff Spicoli before our very eyes,' the media blog Gawker said when the second instalment of the Iran piece came out. In Team America: World Police, Trey Parker and Matt Stone's 2004 marionette film parody of Bush's war on terror, a bubble-headed Penn puppet says of Iraq, 'Before Team America showed up it was a happy place. They had flowing meadows, and rainbow skies, and rivers made of chocolate where the children danced and laughed and played with gumdrop smiles.' Penn shot back a 'sincere fuck you' to the filmmakers, in a letter that was reprinted on news website the Drudge Report; he also offered to retrace his steps with them. 'We'll fly to Amman, Jordan, and I'll ride with you... 12 hours through the Sunni Triangle into Fallujah and Baghdad, and I'll show you around,' he wrote. 'When we return, make all the fun you want.'

Early in 2005, Penn completed filming for Steven Zaillian's remake of All the King's Men, which will open later this year, and in which he plays the mesmeri sing and corrupt Louisiana kingpin Willie Stark, Robert Penn Warren's fictional version of governor Huey Long. His plan now, he told me, was to take a couple of years off from acting. (This wouldn't be the first time that he had taken a break from performing. In the Nineties, he quit for a few years, and threw himself into directing instead.) 'I'm out of fuel,' he said, adding, 'you want to be aware of the impact in terms of just how much you put out there. You want to maintain the potency of aspects of yourself - marshal your forces, select things you can put your heart and soul into. Have time to evolve and reinform the creature who's doing it.' He said that he sometimes has difficulty sustaining his passion over the hard slog of a film shoot. 'You turn on the news, and there's something else you want to make a movie about,' he said. On the other hand, he added, 'If there's anything really valuable for me in the craft of acting, it's maintaining the skills to hold on to the passion I started with.' Acting, he explained, was like parachuting. 'If you jump out of an aeroplane, you love the first 1,000ft. Now you're ready to land, but you're not gonna slow down just because you aren't interested any more. The craft is there to make sure that when you jump you're propelled properly to keep going full speed.'

Penn is an entrepreneur of his own edge - a roiling combination of rage, buoyancy, tenderness and hurt. His struggle to contain this combustible emotional package makes him at once dangerous and exciting. In his art and in his life, he takes chances. ('Sean is batty as a loon and is prone to taking extraordinary risks in foreign towns,' the late Hunter S Thompson, who knew something about recklessness, wrote.) He has been known to hand out to friends cards on which he has printed the epigraph to William Saroyan's Pulitzer Prize-winning play, The Time of Your Life: 'In the time of your life live,' it begins, 'so that in that good time there shall be no ugliness or death for yourself or for any life your life touches.' Penn has the confidence of a man who believes that the world will provide what he needs when he needs it. 'It's trusting your instincts and your experience,' he says. 'Call it fate.'

He is also a fighter. In his gun-toting, paparazzi-punching, midnight-rambling Hollywood years, which spanned the Eighties and early Nineties, he took regular pleasure in publicly biting the hands that fed him. 'What's the difference between yogurt and Los Angeles?' he liked to joke to the press back then. 'Yogurt has a living culture.' But after Penn's wife, the actress Robin Wright Penn, was carjacked in the driveway of their Santa Monica home, with their two young children still in the car (no one was hurt), in 1996, the Penn menage decamped for picturesque, suburban tranquillity about 45 minutes north of San Francisco, where they live in a tile-and-stucco hacienda, surrounded by a large wall that Penn constructed.

Penn likes driving. He's been known to take long, freewheeling car trips around America, especially after a film has wrapped and he gets that 'big fucking school's-out-for-summer feeling', he said in Richard T Kelly's Sean Penn: His Life and Times last year. 'Give me a car and a country I can zigzag through... and I'm a bird.' Even on the short trip back to his house after breakfast, he seemed to enjoy the glamour of himself in motion. He leaned forward over the steering wheel of his black SUV, cupping his hands around his lighter as he lit a Marlboro. I remarked that he seemed like the kind of person who would roll his own cigarettes. 'Oh, no, then I'd be a real smoker,' he said. 'These give me the illusion that I can quit.'

With the cigarette dangling raffishly from his mouth, he was a snapshot of casual, at least until he spotted a police car in his rearview mirror. 'I always think it's me. "Para-fucking-noia, Eddie,"' he said, quoting a line from David Rabe's Hurlyburly. (Penn appeared in the play, in 1988, and also in the 1998 film .) He fumbled through the glove compartment. 'I have a driver's licence,' he said, 'but I don't have it on me.'

Penn has had his share of run-ins with the police. In Macao in 1986, during the shooting of Shanghai Surprise, he was arrested for helping to deter an intruding paparazzo by hanging him by his ankles from his ninth-floor balcony. (Penn subsequently broke out of the jail, where he was being held on charges of attempted murder, and escaped from the country by jetfoil.) In 1987, he served 33 days of a 60-day sentence in the Los Angeles County jail ( 23 hours a day in solitary) for violating the probation he'd been given for punching a fan who tried to get too close to his first wife, Madonna. In 1988, Madonna herself summoned a Swat team to the couple's house in Malibu after the two had fought. ('She developed a concern that if she were to return to the house she would get a very severe haircut,' Penn, who was not arrested in the well-publicised incident, said later.)

For a mile or so, Penn kept careful watch on the police car behind us while he chatted about his children - Dylan's transfer to a private school, Hopper's skateboarding obsession. Then the police car swung into the express lane and pulled up alongside us, and the officer driving motioned in Penn's direction. At first, it seemed that she was signalling Penn to pull over, but she was only pointing at his seat belt. Penn strapped himself in. The police car sped away. 'That's nice,' Penn said. He turned to me and allowed himself a smile.

Penn's office space - two capacious rooms above the garage of his house - has a doormat that reads: Witness Protection Program. He refers to it as his 'afterhours editorial facility' . This is where Penn comes to write, edit, drink, carouse, and wheel and deal. It is also a visible manifestation of his guarded nature. The rooms - decorated in a sort of bordello burgundy, with burgundy velvet wallpaper, burgundy baize on the pool and poker tables, and burgundy chairs - have a crepuscular gloom; they reflect the 'downtown quality' that Jack Nicholson has said expresses 'the dark part of Sean's character... this feeling for lost souls and the kind of green-tinted late-at-night quality'. Penn, of course, has a wide range of well-placed friends, but he seems to be happiest in the company of what his close friend, the musician David Baerwald, calls 'the demidemimonde - the kind of people who might follow Al Capone around'. In this demotic scrum - 'I'm just another American who appreciates a little colour,' Penn once wrote - he feels safe. 'I hang out with guys who are very comfortable not looking at me and not having me look back at them,' he told Playboy in 1991. 'It's like being by yourself without being by yourself.'

'You have to protect your edges,' Dennis Hopper said, explaining why Penn keeps much of the world at arm's length. 'Sean goes deep into his emotional inner life. He allows you to see it, then he closes it back up. He has to, or he wouldn't be able to survive.' Woody Allen agreed: 'He's not easily accessible. It's hard to get through to him, and you feel that at any minute he could blow up at you. It makes it so interesting. Women want to take care of him and men find him heroic.' Penn's elusiveness was established at an early age. His mother, the actress Eileen Ryan Penn, told Richard Kelly that, as a child, 'Sean had his own private little world going.' 'I don't think that I really spoke outside my home till I was five,' Penn told me. 'I remember plenty of conversations, but they were all with myself. If I ever felt loneliness, it was in a group.' Penn's shyness, by his own admission, was also a kind of strategic retreat. 'When I realised that people could not see into me - that bothered me,' he said. 'I wanted to be transparent, so as to be understood. I knew that my intentions were good. It seemed to me I could give a lot more and be more productive with people who could see who I was.' He went on, 'I didn't want to be charming. I didn't want to have to be funny. I didn't want to have to be flawless. I wanted to be able to know my heart was in the right place and not do a big song and dance to display it.' 'The only complaint that teachers ever gave me about him was, "Is he happy?"' Eileen Penn said. 'He seemed to be so quiet.'

In high school, Penn learned that his unreachable quality could be used both to provoke and seduce. 'Being shy brings attention - it brings my subjects to me,' he explained. 'It works the same way it did at high school. There's a lot of noise, a lot of alpha dogs plying their trade. Then, there's you, bouncing your tennis shoes off the brick on the planter you're sitting on. At some point in the school year, a pretty girl reaches a moment of reflection where that becomes more attractive than the alpha dog. You've got a lot of stuff that will be new to share.'

Almost all the characters to whom Penn has been drawn are to some degree cut off from the world, whether by murderous obsession (Samuel J Bicke in The Assassination of Richard Nixon; Sergeant Tony Meserve in Casualties of War; Matthew Poncelet in Dead Man Walking; Jimmy Markum in Mystic River), by mental or physical damage (Sam Dawson in I Am Sam; Eddie Quinn in She's So Lovely; Paul Rivers in 21 Grams), by drugs (Eddie in Hurlyburly, Spicoli in Fast Times at Ridgemont High), or by artistic self-absorption (Emmet in Sweet and Lowdown). But the fury that fuels Penn's performances - 'the wonderful homicidal quality of his rage,' as the screenwriter Nick Kazan describes it - is examined in even greater depth in the three films that he has directed (he also wrote the first two): The Indian Runner (1991), The Crossing Guard (1995) and The Pledge (2001). On the surface, Penn's well-told tales seem disparate. However, the issue at stake is almost always his own: the desire both to connect with and to elude people - to be, in other words, a kind of respectable outlaw. Penn addressed this division most directly in The Indian Runner, which was inspired by Bruce Springsteen's song 'Highway Patrolman'. The film tells the story of two brothers, one a dutiful, family-loving deputy sheriff, the other a violent, unreachable jailbird. 'I think both things exist in me,' Penn said, adding, 'if we're of any use, then we have blood on our hands.'

As Penn and I talked in his office, he noticed me glancing at a plastic Barbie-like doll propped against the fireplace. 'An Ann Coulter doll,' he explained, referring to the neo-conservative TV pundit. 'We violate her,' he said. 'There are cigarette burns in some funny areas. She's pure snakeoil salesman. She doesn't believe a word she says. She mentions Leo in her book Treason.'

Leo Penn, Sean's father, was a movie actor, whose career was blighted in the early Fifties by the Hollywood blacklist. (He died, of lung cancer, in 1998.) According to Penn, Leo was 'the king of comfort in his own skin'. Although Leo was not named in the House Un-American Activities Committee investigations, he was labelled as a fellow-traveller and, by 1952, couldn't work on the West Coast. He moved back east where, he said, 'it took roughly two years and I was dead in New York, too. I couldn't do either film or television.' Nonetheless, Leo built up a considerable reputation as a theatre actor. He soon fell in love with a beautiful, outspoken actress, Eileen Ryan, and they married in 1958.

The Penns were socially conscious, resilient survivors. They moved to California in 1959, and Leo was offered the chance to try his hand at directing for television. He loved the camaraderie of the job. Over the next 30 years, he directed more than 400 hours of prime-time TV, winning an Emmy in 1973 for a special episode of Columbo. But there were times when Sean heard in his father's badinage a hint of disappointment: 'I'd say, "What are you up to?" He'd say, "Ah, you know, trying to make a better piece of shit out of a worse piece of shit."'

Leo had been betrayed by the country that he'd fought for with distinction. As a bombardier in the Second World War, Leo had won the Distinguished Flying Cross and the Air Medal. Many of the hallmarks of Sean's artistic career - his fascination with outsiders, his rebelliousness, his hatred of injustice, his suspicion of authority, his flirtation with heroics - are informed by the legends of Leo's life, of both his military and his political travails. 'One thing that the children of blacklisted people know is that on many levels acceptable polite society is just another fraud,' Baerwald said. 'Leo should have, could have, and certainly wanted to do work of more substance than he did. Life was much diminished.'

When Penn was a child, his parents' bond was complicated but palpable. He remembers his mother and father sitting late at night on their patio in Malibu, looking out at the Pacific. 'If you sneaked out for a snack or something, they'd just be sitting there, lights out,' he told Kelly. 'She'd be sound asleep with her head on his lap, and he would be rubbing her hair.' As we were driving, Penn returned to that memory, but with an additional detail: 'He'd drink a bottle of J&B at night; my mother'd polish off a bottle of Smirnoff. She never started drinking till we were in bed. They could both get up early the next morning and function.' Eileen Penn told me, 'Leo and I drank equally. We enjoyed the drinks. I'm not sorry. If I was like my mother - falling down the cellar steps, me coming home from school with a friend and she'd be halfhanging out of her nightgown... Sean never experienced any of that with me.' But Sean's younger brother, Chris, also an actor, who died accidentally, after taking a combination of prescription and over-the-counter medications in January, at the age of 40, saw a difference between his father's attitude toward alcohol and his mother's. 'I think my father was a hard drinker,' he told me last year. 'I don't think he was an alcoholic.' And his mother? 'I won't go into it,' he said.

Eileen Penn is of Irish and Italian descent, and she has a particularly volatile intensity. After obtaining a science degree from New York University to please her parents, she followed her dream by going to New Orleans to sing in a bar, then becoming a successful off-Broadway actress. She gave up performing when she had children. 'All the passion I had for acting went into being a mother,' she has said.

When Penn was nine, in 1969, his family moved from the Valley to a ramshackle beach house in Malibu. Today, the plot is worth millions, and Barbra Streisand lives at the end of the road. Back then, the community was almost rural, and Penn loved it. He surfed throughout his teenage years, and the sport has had a lasting influence on him. 'I defined surfing then as an art form,' he said in 1991. 'It was truly about matching the energy of the wave. It was a harmony, and there was poetry to it. There was a spiritual aspect to surfing.' Surfing taught Penn both the pursuit of excellence and the habit of bravery. According to his ex-fiancee, Elizabeth McGovern, his co-star in Racing with the Moon, it 'was a sort of parable for his whole life. He's always riding the crest.'

'We were roaming kids,' Chris Penn, who also surfed, rode horses, and sometimes slept overnight on the beach, told me. 'We had a lot of freedom.' Sean said, 'From the time we were very young, it was all about expanding your imagination.' Eileen's gospel, according to her, 'wasn't "Aim high"; it was "Aim out - to life."' She set her children a feisty example. She was also tough to the point of scathing. 'She was a grinding wheel,' Baerwald said. 'I mean, to make a knife, you've got to have a hard surface.' He added, 'I get the feeling she was really, really, really, really rough on Sean.' Penn described his mother's visit to his debut performance: 'I played a part in a stage version of The Young Savages. My mom comes backstage. She took my face in her hands. She looked me in the eye, and she said, "You were just terrible. You cannot do this." Meaning acting. That's my mom.' Penn added, 'About a hundred per cent of my friends were afraid of her.'

'He had to fight me growing up,' Eileen said. Penn emerged from the battle with an unusual carapace of ferocity, charm and strength. Eileen was fiercer with Sean than with her other sons because, as she said, 'he was more like me'. Chris, who was five years younger than Sean, spoke of his brother's 'turbulent' adolescent relations with their mother as 'a very hurtful time for me because I loved them both'. One time, when Sean was particularly cruel to his mother, Chris remembered, 'I basically told him to leave the house - after throwing him around the kitchen, smashing his head against the wall. It wasn't a kids' fight. It was a real fight.' Of Sean's tendency to close himself off, Chris added, 'I can tell you this: that unreachable thing kept me angry at him until my father got sick, in the late Nineties. It was confounding. I don't think it was intentional. Now when he does it - he still does it, he always will - it doesn't bother me any more.' 'I don't think Sean goes into depression,' Eileen told me. 'He creates pain in others so he can fix it. If it isn't there and it doesn't need to be fixed, he can't be the hero and fix it.'

'I'm damaged,' Penn told Rolling Stone in 1996. 'I recognise that.' Penn told me he 'still hadn't sorted out' the source of his rage. 'A couple of girlfriends ultimatumed me into therapy things,' he said. 'I tried but it just didn't play.'

Acting allowed Penn to turn his turmoil to advantage; it also allowed him to live up to his mother's notion of his singularity. Penn was obsessed with the Watergate hearings, and dreamed of becoming a lawyer, but lacked the grades. By his senior year of school, he was cutting classes and carrying a Snoopy lunchbox full of film paraphernalia for Super 8 movies that he was making with Chris and friends like Charlie Sheen and Emilio Estevez. After a brief stint at Santa Monica Junior College, where he studied car maintenance and cinematography, Penn was drawn back to the theatre. 'Acting is the only field I could find where it was all about not having a precedent. It was one that depended singularly on what was different about you.' By then, Robert De Niro's performances had captured his imagination. 'This wasn't a guy who was born with fireworks in his pocket,' Penn said. He didn't have a conventionally handsome face. He didn't have the melodic voice of Gregory Peck. He didn't even have an interest in having those things. One knew how invested he was in what he did. It also struck a chord in me. I needed to do something 100 per cent. I hungered for a process that would leave no stone unturned.'

At the outset of his career, according to Chris, Penn 'didn't have a flamboyant or entertaining presence at all', but he 'worked as hard as an Olympic athlete'. 'The thing Sean had was guts,' Eileen has said. 'The talent came later.' From the age of 18 to 20, five hours a day, five days a week, Penn trained with method-acting coach Peggy Feury, who counted among her clients Anjelica Huston, Michelle Pfeiffer and Jeff Goldblum. Feury was 'interested in how are you gonna bring yourself to the material rather than the material to you', Penn said.

On his 19th birthday, Penn got his first professional part - on the TV detective series Barnaby Jones . A year later, in 1980, he went east looking for work; almost immediately, he landed a part in a Broadway play. Two years later, he was cast in a cameo role in Fast Times at Ridgemont High; after the early rushes, his role was expanded into a star turn. Art Linson, one of the film's producers, told Richard Kelly, 'The famous scene where Spicoli comes late to class and Ray Walston rips up his card, and Sean says, "You dick!" - Ray Walston didn't know who Sean Penn was. So he says his line, "I think you know where the principal's office is." And Sean says, "You old, red-faced motherfucker... " Ray Walston turned beet-red and got crazy pissed off, like, "How dare this kid?" But Sean, even then, was trying off-camera to get a rise out of him that would be great for the moment. That's a pretty audacious move for a kid who no one had heard of yet.' Fast Times made Penn a renegade legend and won him instant membership in the fledgling Hollywood talentocracy known as the Brat Pack.

'Each time, Penn comes as a complete surprise,' Pauline Kael wrote in her review of 1983's Bad Boys, in which Penn played a teenager in juvenile detention exacting revenge on another inmate. She explained, 'He gets so far inside a role that he can make even a sociological confection such as this hero... someone an audience can care about.' Penn often approached characters from the outside in, which was a bone of contention with his mother. When he was about to go on location as a drug dealer spying for the Soviet Union in 1985's The Falcon and the Snowman, Penn told Eileen that he would be changing his hair and teeth for the role. 'Just act the part,' she said. 'You don't need all that make-up.' Later that day, Penn invited her over to his house. When she got out of the car, a man came to greet her. 'Hi, Mrs Penn,' he said. She vaguely recognised him, thinking, 'He was probably some friend of Sean's from school.' 'Remind me, I know you, I know you,' she recalled saying. 'And he's walking toward me. "You're... Oh my God, you're my son."' He was wearing the make-up he planned to use for the part. 'Gotcha, Mom,' he said.

But it wasn't until 1988, when he was playing Eddie, the coked-out Hollywood casting agent in Hurlyburly, at the Westwood Playhouse in LA, that Penn achieved, in his eyes, a balance of discipline and expression. 'Charlie Parker - or one of those guys - once said he played an A chord for half an hour before he heard it,' he said. 'I was playing the chords of this stuff for years and then, within the course of that play, I heard what it was I was trying to say and why I was trying to say it.' During the interval on opening night, the actor Robert Culp tapped Eileen on the shoulder. 'You've got a Stradivarius,' he said. The film version of Hurlyburly brought out all the emotional daring of Penn's technique. In it, he condensed the turbulence of his young adulthood into an almost visionary embodiment of Rabe's hilarious and horrible portrait of moral collapse. 'Twenty years ago, it was internal combustion,' Penn told me of his own life. 'There wasn't anything that resembled peace in my spirit.'

In 1996, Penn and Wright, after six years together, followed by a fraught period of separation, were married (their children were five and two). The newfound maturity of his private life has been reflected in the range and depth of his screen performances as well. Over the past decade, his restraint has become more elegant, his reservoir of feeling more profound. The breakdown of the death-row killer Matthew Poncelet, in Dead Man Walking , and Jimmy's grief-crazed fury over the murder of his daughter, in Mystic River - for which Penn won an Academy Award for Best Actor in 2003 - are among the high-water marks of contemporary acting. Penn has drawn frequent comparisons to Marlon Brando, who was a friend of his. Brando, however, was never known for his light touch; Penn has one if he needs it. 'I know I haven't shared as much joy - pure joy - and humour as I might experience in life,' he said. 'I'm predisposed to hold back.' But, as he demonstrated in Sweet and Lowdown, his reticence can be spice to comedy. 'Sean can do lighter material,' Woody Allen says. 'He can deliver a line if he has to. He's just lucky that way.'

Penn was driving me back to San Francisco when his mobile rang. Wright needed the car by two. 'So let's have dinner tonight,' I said. Penn mumbled something about making a start on his Chronicle article. 'I'll get back to you,' he said. At around five, the hotel phone rang. 'Meet me at Tosca's at 5.30pm,' Penn said. He told me that he had made a dinner reservation at a Vietnamese place near Tosca's, a nondescript saloon which serves Penn variously as watering-hole, mail drop and clubhouse. When I walked into the dim glow of the bar, he wasn't there. I took a stool, ordered a beer and settled down to watch the only two other people at the bar, who were going through the rituals of a first date. After 15 minutes or so, I asked the bartender, 'Sean been in?' 'Yeah,' he said. 'He and the boss went out for dinner.'

About half an hour later, Penn walked in with Jeanette Etheredge, Tosca's owner. 'Everybody needs a bar in their life,' Etheredge said; over the decades, hers has played a part in the carousing lives of Hunter S Thompson, Francis Ford Coppola, Dennis Hopper and William Kennedy, among others. Penn told Etheredge that he'd be back soon and then, without mentioning that he'd already had dinner, he headed out with me to the Vietnamese restaurant.

Over dinner, I repeated a story that his mother had told me, about talking to Woody Allen on the set of Sweet and Lowdown. 'Woody said he's always wanted to work with Sean, but couldn't figure him out,' Eileen had said. 'I'll sum it up for you, Woody,' she replied. 'He's embarrassed at having had a happy childhood.' Speaking of his mother earlier that day, Penn had said, 'She has rewritten history quite a bit.'

He was just about to comment on the story when his mobile rang. 'I'm sorry,' he said. 'I'm on kid call.' After he hung up the phone, Penn looked down at his half-eaten appetiser; the sight of food led him to a meditation on 'the hunter-gatherer aspect of things'. 'Hunting isn't necessary in the world we're living in,' he said. 'A man can go and hunt elk if he wants. But the woman can get to the market sooner than that and bring home the food. So what's left? Violence. That's it. There's no identifiable venue for the system of alpha.' The waiter took away our plates. Penn pushed himself back on the banquette. 'I'm full,' he said. 'You want anything else?' I demurred. Penn called for the bill; he insisted on paying.

Back at Tosca's, where the habitues were now three deep at the bar, arms were raised - not to cheer on the Giants on the TV but to hold up camera-phones as Penn made his sprightly progress to the back room. When he paused to talk to Etheredge at the end of the long bar, a young Asian man shoved a phone into his hand and asked him to speak to his father, who was celebrating his birthday. 'Your son really should watch his drinking,' Penn said into the phone. 'Happy birthday.'

The back room was as cramped and musty as a shebeen. The space was lit by a yellow neon sign that said 'Tosca' and the green glow of a shaded bulb over the pool table. Film posters haphazardly plastered to the walls added to the room's subterranean panache. Penn was at home. After he'd had a couple of vodkas, his mood lightened and his guard lowered. At one point, talking about his friendship with the magician David Blaine, Penn leaned across the table and said, 'Why are we close friends? I don't ask. I don't want to know. Love the mystery. Don't want to know why I'm here, per se, in life. Feel it, follow the feeling. But don't want the answer. Don't want the safety net of "Am I gonna have an afterlife or am I not?" Somebody says there's a God, I think it's a kind of funny notion. Somebody says there's not, I think it's a funny notion. To know is a funny notion. And so, you know, if I've got a religion, it's the mystery of the thing.'

After a while, Penn led me upstairs to another dingy inner sanctum, where two off-duty policemen were sitting at a table, discussing the recent suicide of one of their cohorts. Penn knew the men and asked if they minded our presence. They waved us in. We settled into an alcove. Penn reached into his pocket and pulled out a sheaf of typed pages. 'First rough,' he said, and in hushed tones he began to read: 'Jet lag had cut me down around midnight the day of my return from Tehran. But my fractured body clock sounded its alarm at 4.30am the following morning. I got up, went to the kitchen, flipped on the TV and surfed my way through the channels, landing on CNN's American Morning with Soledad O'Brien... She reported me to be currently in Tehran for the San Francisco Chronicle... Then, as footage of me from a well-meant farewell given me by the Iranian Film Society played, she observed that I looked to be playing a journalist. So here we begin, as I sit in my kitchen in California, she's reporting me to be in Tehran. She looks at the film given her by a producer and jumps on the bandwagon of attack... Let's set the record straight, shall we? From the moment the international press became aware of my presence in Tehran, the predictable misreporting began deluging websites, newspapers, television and radio in the United States and around the world. The inaccuracies ranged from claiming me a pro-Iranian, anti-American lefty, to a continuous and lazy presumption that my first and highly criticised trip to Iraq had been supported by the San Francisco Chronicle... What's disturbing here goes to the heart of the misunderstandings throughout the world and to the heart of freedom. And the free press is only free when it is bold and accurate. And while the dismissive and trivial attacks on me may be the bickering of details, the number of dead and the purpose of war are not.'

Penn read for about 10 minutes, glancing up occasionally to see my reaction. After five pages, he was just about to disembark from the plane in Tehran. I suggested that perhaps he should get to Iran earlier in the piece. He nodded, but said nothing. (Stripped of some of its vainglory and verbosity, the edited version of Penn's essay became the Chronicle's most-read story of the year, with more than half a million hits on the newspaper's website.)

Back downstairs, Penn made a beeline for Gavin Newsom, the mayor of San Francisco. He was soon in animated conversation with Newsom and his then wife, Kimberly Guilfoyle Newsom, a former lingerie model who was an anchor for Court TV. Penn, as the world knows, likes a good time; he is also expert at provoking one. There was no dancing that night, but, toward the end of the evening, there was a song. Penn smiled, drink in hand, and leaned close to me as he intoned the lyrics to one of Baerwald's compositions: 'Fifteen long years on a losing streak/and a lot of bodies unburied/and there comes a time when you cannot turn the other cheek/ you have got to ride the ferry/past the battered old bodies/of dead dead dreamers/past the tethered and fettered and desk-bound schemers/ the punks and the drunks and the/bad guitar players and the dewy-eyed/teenage dragon slayers... ever hopeful and ever blue we/do the things that we know we have to do/and though we all know deep down in our hearts/ that someday this will all fall apart/for right now, let's just be heroes.'

The next time I saw Penn, he was a hero. It was September, and he was on my television screen, wading chest deep in a New Orleans sump, trying to reach a survivor of Hurricane Katrina. Over the next 48 hours, I caught fleeting sight of Penn brandishing a rifle; lugging old people out of his boat; bailing out the boat; and, later, just off the plane to San Francisco, cleaned up and remarkably composed, being interviewed by Larry King. By then, although Penn had helped to rescue about 40 people, the press and the bloggers had done their sneering. 'Sean Penn, International Man of Action,' it was reported, had come to New Orleans with his 'entourage', including a photographer; the boat he was seen bailing out was widely reported to have sunk. None of this proved to be true. When King pressed him about the story of the sunken boat, Penn responded with a bet. If the newspaper that had first reported the sinking - Melbourne's Herald Sun - could produce any evidence of it, he'd pay out $1m; if it couldn't, it should pay $1m toward disaster relief for the Katrina victims. The story went away but, as I discovered a few days later in San Francisco, Penn's irritation did not.

In jeans and a black bomber jacket, Penn was sprawled barefoot on his office sofa when I arrived, around midday. Dazed and unshaven, he looked rough. Bottles of vodka and red wine were open on the coffee table beside him. Before we talked, he insisted that I read something he'd written for Rolling Stone. 'Watching the scenes of devastation on my television set was like standing behind the tape line at a traffic accident and watching a child slowly bleed to death unattended,' it began. 'I'm not gonna tell you I wasn't very, very pissed off,' he said about the press coverage of his rescue mission. 'The whole reason I didn't go sooner was that I worried I'd be in the way. I was not in the way. Listen, most of the rescues were done by civilians. It's so disheartening that people are diabolically detached.'

As the hurricane was unfolding, Penn, who had spent some time in New Orleans, stayed in regular contact with political pundit James Carville, who is also one of the executive producers of All the King's Men, part of which was shot in New Orleans. At first, Penn was assured that everything that could be done was being done; then the Superdome lost its roof, and it became clear that the city was imploding. 'Carville, at a certain point, said, "Fuck it, do what you think,"' Penn said. He told his family he was going to the Astrodome in Houston and maybe to Baton Rouge. 'I didn't tell them I was going to New Orleans. I didn't know I was gonna get in, but I had a feeling.' He also organised a small jet to fly to Baton Rouge with supplies.

As Penn told his story, he still seemed to be trying to make sense of the experience; words tumbled out of him in a sort of Cubist report of fractured time and vivid details: the prop plane he took from Houston to Baton Rouge; the police car that carried him into New Orleans; the darkness of the city; the empty streets; finding a boat; the adrenaline, the bewilderment. A preacher called Willie, who knew of 40 kids trapped in a school, became the navigator on Penn's boat while he manned the bow, watching for submerged cars. It was a beautiful day; the water was black. Bloated bodies floated by, 'all in the same position: face down, spreadeagled'. Penn, who had been vaccinated for infectious diseases for an African safari earlier in the year, had no problem spending nine hours in the contaminated swamp. 'I saw three non-civilian boats,' he said. 'What was surreal was the lack of presence of official people - the National Guard, the United States Army, the state, the New Orleans Police Department. There just weren't nearly enough of them.'

Penn didn't stop to draw breath. He recalled a two-story building that had lost its entire front wall. 'You were looking right into people's bedrooms,' he said. 'And, upstairs, in his boxer shorts, was this Middle Eastern guy with a shotgun and with Islamic symbols painted on the walls. He didn't want anything to do with us.' Penn took a drag on his cigarette. He recalled a schizophrenic woman who had been days without her medicine, chest deep in water, groping toward a helicopter as it descended noisily toward her. 'We were yelling at her to turn and come to us,' he said. 'She didn't hear us. Shingles flew off roofs and all that kind of shit. The water was like an ocean. I turned my back because the water was kicking the hell out of us. Somebody starts screaming. I turned around and she's gone underwater because of all this turbulence. That's when I ended up in the water. We got her. We got a few others on that run.'

At the end of the day on the water, Penn returned to the Garden District where he and friends had ferried the people they'd rescued. All of them were still waiting at the water's edge. 'Nobody was there for decontamination, nobody was there for medical relief, nobody was there to transfer these people out of there,' Penn said. He spent the rest of the night shuttling the rescued victims to a clinic.

Now that the situation in New Orleans was no longer about emergency response, Penn declared himself 'a little depressed about it'. He said, 'When it was about pulling people out of water, that's a no-brainer.' But, 'Where do they go? How do you feed them? How do you get them to start their lives again? How do you figure out who's the child molester? Now I'm as confused as the government about what to do. I struggle with the notion that my mind doesn't go far enough. I'm always frustrated by intellectual restrictions. My frustration's with my brain, not with my heart. My heart's clear. I don't have a problem there.'

In his interview with Larry King, Penn pulled his punches about President Bush and his late response to Katrina. Nonetheless, over the years he has consistently sought to get right up under Bush's chin. For the Chronicle, Penn tried, and failed, to interview the president; in the run-up to the invasion of Iraq, he famously paid $56,000 to publish an open letter to Bush on a nearly full page of in the Washington Post: 'Many of your actions to date and those proposed seem to violate every defining principle of this country over which you preside: intolerance of debate... marginalisation of your critics, the promoting of fear through unsubstantiated rhetoric, manipulation of a quick comfort media, and the position of your administration's deconstruction of civil liberties all contradict the very core of the patriotism you claim,' he wrote.

In the same letter, Penn invoked his father: 'He raised me with a deep belief in the Constitution and the Bill of Rights.' 'My dad was a hero to all of us,' Chris Penn told me. 'I think it's easy to say that Sean wants to be a hero. I see what he does around the world and, you know, I think that his heart's always in the right place. And is some of it wanting to have a little credit as a hero? Maybe. I think there's also a kind of innocence, which my father to a degree had. I think I'm a little too cynical. Most heroes get killed.' Baerwald agreed: 'I think there's a part of Sean that isn't gonna be happy until he gets murdered by the Republican noise machine. Until he finds out what it's like to feel like his dad.'

Penn took me downstairs to the kitchen, where Hopper was studying an earth-science textbook at the vast blond-wood kitchen counter, waiting for his father to check his homework. 'Give me a few minutes,' Penn told Hopper. Turning back to me, he said under his breath, 'I used to hate doing homework.' He led me out of earshot, to a patio overlooking a walled garden and the pool. 'I'm under investigation by the Office of Foreign Assets Control, the Treasury Department,' he said. 'It's a fiveyear investigation. Did I violate the embargo by going to Iraq under Hussein? Did I spend money? Did I use my American passport to get there? All those things. The answer to those questions is no.' He added, 'We know it came from the White House. My lawyer in Washington knows that.' Penn has been told by friends in the LAPD that he is under surveillance.

On the way out, Penn had paused at a side table. 'There's a cool picture of my dad here,' he said. 'That's him directing.' In the photograph, a viewfinder was hanging around Leo Penn's neck; his jaw was tight and his chin assertively thrust forward. We stood together for a moment, scrutinising the image of command, and I thought of something that Penn had told me earlier in the day. 'My dad loved humans and humanity,' he'd said. 'I'm good on humanity.'

(John Lahr's Honky Tonk Parade: New Yorker Profiles on Show People will be published by Duckworth in September)