Saccharum Hotel, Calheta - save 31%
TalkTalk have created this exclusive biography of Sean Penn - we believe it to be the most comprehensive on the web
Seldom has cinema seen a more controversial figure than Sean Penn. Breaking through as a Brat-Packer at the beginning of the Eighties, he looked set for a mighty mainstream career but, having married Madonna in the first burst of her phenomenal success, instead spent much of the decade flailing at the paparazzi, desperately battling for privacy at the eye of a media storm, even getting himself jailed. Quitting acting altogether, he reinvented himself as an art-house director and, returning to the peripheries of the Hollywood fold, as a consummate character actor, being nominated three times for Oscars, then winning Best Actor for both Mystic River and Milk. Yet the fire of rebellion still burned as, publicly rubbishing most of Tinseltown's output, as well as America's foreign policies, he was constantly on the edge of a mighty furore.
His refusenik roots were deep. His father, Leo Penn, was an actor, writer and director during the McCarthy era. Called before the Un-American Activities Committee, he refused to name names, was branded a Communist and blacklisted - forcing him to move into TV. One of Sean's earlier memories is of his father taking him to the set of The Last Tycoon - starring Robert De Niro and Jack Nicholson - near to the family home. Passing through, Leo was hailed by the movie's director, Elia Kazan, who HAD named names. But Leo, normally warm and friendly, walked straight past, his passionate integrity leaving an indelible mark on his son.
As far as Sean's later career went, Leo was not the only one to draw him towards movies. For Sean's mother was Eileen Ryan, a well-known TV actress who appeared in most of the big shows - Bonanza, Marcus Welby MD etc. She'd take a near-two-decade gap to raise her three children - Sean, younger brother Chris (also a fine actor), and Michael (now a musician, he soundtracked Boogie Nights and is married to Aimee Mann). Then she returned in the likes of ER, Ally McBeal, NYPD Blue and CSI, as well as Parenthood, Magnolia, and many of Sean's projects.
The family spent Sean's first ten years (he was born in Burbank on the 17th of August, 1960) in different parts of California's San Fernando Valley, from North Hollywood to Woodland Hills. Then they moved to Malibu, where Sean attended Santa Monica High School and became a surf nut - as it happens, perfect research for the role that would first make him a star. Living near Martin Sheen, Sean's friends and schoolmates included Emilio Estevez and Charlie Sheen, as well as Rob Lowe, and the gang ran wild together, occasionally pausing to shoot shorts on Super 8.
Though he had thought of becoming an attorney, Sean's interest in film-making grew too strong to resist. It's often been said that his path to fame was easy, because of his parents, his friends and, eventually, his first marriage. But Sean started work early, skipping college to spend two years with the Los Angeles Repertory Company. Here he worked backstage, cleaning, carrying and gradually learning to act, working as assistant to actor/director Pat Hingle. He directed a one-act play called Terrible Jim Fitch, played in local theatre, and studied under the legendary acting coach Peggy Feury.
Of course, being Leo Penn's son did help. Leo was a major TV director throughout the Sixties, Seventies and Eighties, helming episodes of Star Trek and Lost In Space, Dr Kildare and Cannon, Columbo, Starsky And Hutch and on to Fame, Cagney And Lacey, Magnum PI and St Elsewhere. Sean had made his screen debut back in 1974, alongside his mother in The Little House Of The Prairie. Now, in 1979, he made his pro debut in a dad-directed episode of Barnaby Jones. As you'd expect, it was quite a controversial episode where counsellors were found to be dealing dope and killing people in a rehab school for young addicts. It was also packed with future stars, Ed Harris playing the bad counsellor, and Madeleine Stowe featuring, too. Leo was also in charge of Sean's TV movie debut, Hellinger's Law, an unsuccessful pilot starring Telly Savalas.
But it was as part of the much-vaunted Brat Pack that Sean really first broke through. First came another TV movie, where he played the title role in The Killing Of Randy Webster, as a kid who's shot by Houston police and whose dad will not accept the official version of events. Also in the cast were Jennifer Jason Leigh and Anthony Edwards, later to hit big with ER. Then came Harold Becker's Taps, where Timothy Hutton played a military cadet who leads a mutiny to stop his 141-year-old academy being taken over by developers. Alongside Tom Cruise, Sean was superb as his feisty brother-in-arms, and a Hollywood buzz began that he was the Next Big Thing.
It should be noted here that Sean did not get the Taps role through the influence of his parents. In fact, having grown dissatisfied with TV, he'd bought a one-way ticket to New York to gain stage experience. Back home he'd appeared in Earthworms, in New York he went for a part in Heartland. His first reading was terrible, but his second won him the role, and the role won him both rave reviews and the part in Taps. Sean would occasionally return to the theatre in later years, in The Slab Boys in 1983, in Hurlyburly in 1988 (ten years later he'd get the movie made) and, in 2000, he played alongside Woody Harrelson, Nick Nolte and Cheech Marin in The Late Henry Moss, written by Sam Shepard, one of Sean's heroes.
After Taps came Fast Times At Ridgemont High, the first big one for both Sean and writer Cameron Crowe. Penn stole the show as Jeff Spicoli, drawing on his surfer experience to play the ultimate drop-out dude, antagonisng the teachers, ordering pizzas from the classroom and introducing the national catch-phrase "Let's party!" Alongside him once more were Leigh and Edwards, as well as Judge Reinhold, Eric Stoltz, Forest Whitaker and Nicolas Cage. Then came a real change of pace with Bad Boys, where Sean played Mick O'Brien, a kid sent to reform school (ie jail) for accidentally killing a guy. Unfortunately, the dead man's brother is inside too and wants revenge, with the fabulous Clancy Brown joining in - Penn being gradually brutalised and driven towards screaming ultraviolence. This was where Sean's habit for heavy-duty role-research really began, when he spent time on the job with the gang-crimes unit of the Chicago police.
Already, Sean was seeking out-of-the-ordinary roles, shying away from roustabout Brat Pack comedies. First came Racing With The Moon, where Penn and Cage played two friends waiting to enter the war with the Marines in 1942, and seeking what might be a last shot at summer romance. Sean would begin a relationship with co-star Elizabeth McGovern, briefly getting engaged but splitting the next year.
Next came the dark, serious Falcon And The Snowman where Penn excelled as weasely scuzzball and dope-fiend Daulton Lee, persuading friend Timothy Hutton to sell government secrets to the Russians. Then there was Louis Malle's Crackers, starring Donald Sutherland, about a crazy gang of incompetent crims who go on a nutty spree. Prophetically, it was a remake of a movie called Big Deal On Madonna Street.
Prophetically, because the next four years of Penn's life would be dominated by his relationship with Madonna Louise Veronica Ciccone. Throughout 1984, Madonna had gradually come to rule the US charts, the year ended with her Like A Virgin single at Number One, with its parent album soon to follow it to the top. Well-known for a succession of celebrity boyfriends, now she met Sean Penn - according to Madonna, it happened like this. There she was, about to descend a heavenly staircase while filming the promo vid for Material Girl when she looked down and saw Penn, invited along to the shoot by its director, his friend Mary Lambert (later to helm the glorious Pet Sematary). Madonna would claim that at this moment she had a fantasy that she and Sean would meet, fall in love and get married.
They did meet, and had their first date at the Private Eyes club in New York. The press went mental - here was pop's newest phenomenon dating the reincarnation of James Dean, the angry, hard-drinking, artistically-driven Penn. Penn immediately took exception to all the attention, regularly taking a swing at photographers who constantly hounded the couple. But they couldn't be stopped. Madonna was suddenly a film star, with Desperately Seeking Susan now a big hit, her Virgin Tour was a mighty sell-out, her albums were selling in the millions. Still, this was love. Sean proposed in July in Nashville, while Madonna bounced naked on the hotel room bed. There were rumours that she was already pregnant, that Sean wanted the child but she terminated the pregnancy due to her crazy schedule (she did later say "Sean wanted to have a child. It wasn't the right time").
Once the engagement was announced, the press got even more intrusive. In Nashville, Penn attacked two of them with a rock, being charged with assault and battery and receiving a fine and a suspended sentence. Then, in August 1985, came the wedding, at the cliffside California home of millionaire developer Kurt Unger. Madonna themed it on Cinderella, dressing herself in Grace Kelly '50's style. Sean meanwhile, outraged by the lack of privacy, wrote "F*** Off" in giant letters on the sand. He had good reason, the ceremony was made inaudible by press helicopters overhead - but he got into more trouble for shooting at them.
While Madonna was engaged in world domination, Sean's career pretty much dried up. But first there was one last triumph, with At Close Range, filmed before his marriage. Here, with his mum Eileen Ryan playing his grandmother and brother Chris his brother, he was Brad Whitewood Jr, a kid from the middle of nowhere who seeks adventure and self-esteem by joining a crime gang led by his estranged dad Christopher Walken. This was American gothic at its very best, with Penn superb as the needy innocent way out of his depth in the company of the supremely evil Walken. The film was well promoted by its theme song, Madonna's Live To Tell, which went to Number One.
A couple of months previous to the release of At Close Range, in March 1986, there had been more trouble. Sean and Madonna were together filming a movie to be titled Shanghai Surprise and the press harassment became ridiculous. Much later it would be revealed that, while filming, Penn would discover a prying pap in his hotel room in Macao. Seizing the man, he'd hang him by his ankles from the window, nine floors up. For his pains he'd be arrested, then proceed to break out of jail and flee to Hong Kong in a hydrofoil. Around the same time a photographer from the Sun was knocked over by Penn's motor, the tabloids going ballistic, telling all manner of stories about tantrums and terrible happenings on-set. It grew so bad that the producer, George Harrison actually called a press conference to calm things down. The press would not forget, though, and reviews for the movie, where Penn played a fortune hunter in China and Madonna a missionary nurse, both of them after stolen drugs, were vicious.
The relationship was now horribly stormy. Madonna was still on the up, but Sean was nowhere. He was arrested and given one year's probation for punching a man who tried to kiss Madonna in a nightclub. He then violated that probation by hitting an extra on the set of his next picture, Colours, for trying to take his photograph. For this he'd be sent to the LA County jail, eventually serving half of a 60-day sentence. Tales of fighting, assault, screaming rows were commonplace. In December 1987, Madonna filed for divorce, but changed her mind a week later. It made little difference for, just over a year later, in January 1989, she filed again and this time moved into a new house. This time it was for real. She'd had enough - though she did drop assault charges she'd brought against him.
The end of the marriage saw both Madonna and Penn at an artistic peak. Madonna would quickly release one of her finest and most controversial singles, Like A Prayer, while Penn would appear in a succession of fine features. He'd really come back in 1988 as Robert Duvall's arrogant, violent rookie partner, chasing down LA street gangs in Dennis Hopper's Colours (Penn had actually taken Colours to Orion himself, suggesting Hopper as director). Then there'd be Judgment In Berlin, where Penn played Gunther X, perpetrator of a hijack in East Germany. The judge was played by ex-neighbour Martin Sheen, the director was Leo Penn.
But the big events came in 1989, proving Penn's class once and for all. First, in Brian De Palma's Casualties Of War, he played the genuinely nasty Meserve, leader of a group of soldiers in Vietnam who rape and kill a young girl, only to be accused and brought down by Michael J. Fox. Then he starred alongside De Niro, as convicts pretending to be priests, in Neil Jordan's comedy We're No Angels. Then came perhaps Penn's finest movie, State Of Grace. Here he was Terry Noonan, an ex-member of the Irish mob and now an undercover cop. He returns to try to stitch up old boss Ed Harris, but becomes reacquainted with his former best friend Gary Oldman and his sister Robin Wright. It's violent stuff but the ensemble acting is amongst the best modern cinema has produced.
Various decisions were now made that would change Sean's life. First, he began a relationship with Robin Wright, a quite brilliant actress then best known for the title role in The Princess Bride. The couple would begin living together in 1991, and would have two children - daughter Dylan Frances and son Hopper Jack (named after Dennis and Nicholson) - before getting hitched in 1996. Theirs would be a tough road. Their Malibu home would be burned to the ground in the forest fires of 1993 and the couple, constantly at war, would split, with Penn living in a trailer on the burned-out lot. They'd go back and forth, splitting and reforming. He'd be seen with Elle MacPherson and singer Jewel, who he "discovered" and one of whose videos he'd direct (he's also performed that task for Shania Twain, Lyle Lovett and Wire). In 1995, he told journalists Robin had dumped him, but a year later she took his name, henceforth being billed as Robin Wright Penn.
The other decision was to retire from acting. After the Madonna fiasco, he felt that his public image might "sully the purity" of his work, so he turned to writing and directing with The Indian Runner, starring David Morse and Viggo Mortensen as two brothers, one a good cop, one a crazed vet, who've lost their farm in Nebraska. Also appearing were Sean's mate Hopper, Charles Bronson and a young Benicio Del Torro. The movie, inspired by Bruce Springsteen's Highway Patrolman, was quiet, meaningful and quite fraught.
Of course, as an admitted "acting addict", he couldn't stay away for long. And thank God because his next major role was one of his very best. Back with De Palma in Carlito's Way, he wore specs, frizzy hair and a bald patch to play Kleinfeld, the coke-addled lawyer who ruins ex-con Al Pacino's attempts to go straight. Penn was brilliant - panicked, over-confident, massively generous and incredibly sleazy, just right. At last he received industry recognition with a Golden Globes nomination.
Sean's next role was also tremendous. In Tim Robbins' Dead Man Walking, he played Matthew Poncelet, a prisoner on Death Row who's befriended by nun Helen Prejean (played by Robbins' wife and Penn's old flame Susan Sarandon). Based on a true story, the film was exceptionally moving, managing to show sympathy for the killer, the victim and all those around them. Sarandon won the Oscar for Best Actress, Sean was nominated as Best Actor.
Having got married in 1996, and suffered palpitations when Robin was carjacked and only just persuaded the attackers to let her take the kids out of the car before they drove off, Sean began to get really responsible. The family would move to Marin County, north of San Francisco, to a 6000 square foot home with pool, tennis court and film editing studio (he'd also get a 34 foot boat), where he could work and the kids could grow up safe and un-Hollywood. He'd cut down his drinking and (nearly) give up smoking (he saw his dad die of lung cancer in 1998, but still couldn't break the habit).
And he'd get down to his art. Even when drinking heavily, Sean was interested in that. In fact, he'd often combine the two by drinking with the likes of Charles Bukowski. For years he'd been friends with enigmatic, "disappeared" director Terrence Malik, driving down to Austin to see him (Malick would later cast him in The Thin Red Line). He'd really been interested in all the great mavericks on the outskirts of cinema, in particular John Cassavetes. In fact, for years he'd wanted to appear in the Cassavetes-penned She's So Lovely. But Cassavetes died of cirrhosis, and his replacement as director, Hal Ashby, died of cancer, so it was shelved.
Shelved, that is, till John's son Nick stepped in. Now Penn could star as the wayward, drunken husband of Robin Wright who, in his prolonged absence, marries good guy John Travolta. It was an intriguing, fairly bleak but really well-acted piece, but Nick Cassavetes remembered the shoot as tough. "The beginning and end of every day is how Sean and Robin are getting along. You would think 'Buddy, get over it'. But if they have a bad morning, Sean's broken up about it". This was, of course, the difficult period before their marriage. Sean described his feelings as "irrational obsession".
She's So Lovely was followed by two big budget films, setting the seal on Penn's future working practices, flitting between large and small projects. Now came Oliver Stone's stylised outback thriller U-Turn, where Sean played drifter Bobby Cooper who gets drawn into a web of deceit and danger by sultry Jennifer Lopez and her hubbie Nick Nolte. And then came The Game, by Seven's David Fincher (who, coincidentally, had directed Madonna's Express Yourself video), where Sean played the brother of jaded rich man Michael Douglas, as a present buying him entry to the titular game.
Next, he appeared briefly alongside Robin in Loved, then again in the film version of Hurlyburly, concerning a bunch of repulsive Hollywood beasts - Penn taking Best Actor at Cannes. Then came The Thin Red Line. Here occurred one of the most terrifying events of Penn's life. On a break from filming, in Australia, he found himself suddenly seized at gunpoint and used as a human shield against the police. Shouting "Don't shoot! It's alright, man, calm down!" he found himself forced out into the street where he found cameras whirring and his co-star Woody Harrelson doubled over with laughter. Penn did not forget the trick. Later, the pair of them driving through the outback , he pretended the car was stuck. Harrelson got out to push and Penn took off, leaving him there in the middle of the night with no food, no water and no way home. Eventually, he was picked up by an extra on their way to work.
Penn continued with his directing work, now making The Crossing Guard with Jack Nicholson, Angelica Huston and Robin, where Nicholson played a cop driven to revenge himself on the drunk driver who killed his daughter five years previously. Then there was The Pledge, with Nicholson again starring (along with Robin) as a detective obsessed with unsolved child murders. For this Penn drew together an extraordinary cast, including Vanessa Redgrave, Helen Mirren, Benicio Del Torro, and Penn's own heroes Sam Shepard, Mickey Rourke, and Harry Dean Stanton. "Sean's a very poetic, hard-nosed director," commented Nicholson. "He goes his own way. He's all about being substantial in the work".
As an actor he'd also seek out interesting work. The year 2000 would see him in Kathryn Bigelow's The Weight Of Water where he'd play a drunken poet accompanying his photographer wife Catherine McCormack as she visits the coast of New Hampshire to research the 1873 axe murder of Norwegian immigrants. Sharing their yacht are Penn's brother Josh Lucas, and his sexy girlfriend Elizabeth Hurley. Now the film juxtaposes the jealousies and betrayals of the present and past, relationships on the yacht breaking down badly while, back in 1873, a fantastically unpleasant Katrin Cartlidge rules the roost. Pinch-faced and hard-wired to hurt her sensitive sister, Sarah Polley, she brings disaster down on her house. Another fascinating Penn feature would be Before Night Falls, the tale of homosexual poet Reinaldo Arenas as he finds inner freedom and suffers terrible persecution in post-revolutionary Cuba. Johnny Depp would make two separate cameos, with Penn appearing near the beginning as a peasant riding a horse and cart down a country road, getting the young Arenas to pick up a discarded cigar butt for him, then taking him towards the rebels he wishes to join. The movie had deep political, social, sexual and artistic messages - it was just where Penn should be.
Now, there were two more prime roles. First, Sean starred as irresponsible, drunken, brilliant jazz guitarist Emmet Ray in Woody Allen's Sweet And Lowdown, earning himself another Oscar nomination. Then came I Am Sam, where he played Sam Dawson, an adult with a mental age of 7 who hits trouble when his daughter reaches that age, their relationship begins to break down and the authorities want to take her away. He guilt-trips flash lawyer Michelle Pfeiffer into taking his case and shows her the meaning of true love. Penn researched the role by visiting the LA Goal centre (two of the residents are in the movie, as Sam's friends), folding teeshirts and stuffing envelopes and both watching and befriending those with development disabilities. Yet again, he was Oscar nominated.
Naturally, he wasn't at the ceremony, feeling most great performances are overlooked. "I'm not somebody you'd want to go to most American movies with," he told Rachel Abramowitz. "I'd really upset you. I get crazy. I feel like they're all up there saying 'You're an idiot! You're an idiot!'" He's even called Gone With The Wind "an abominable fraud of a movie" and stated that we should burn all old movies and start again (not a bad idea in the case of Shanghai Surprise).
As befits the man, there was also some more serious controversy afoot. In 2002, as George Bush Jr was gearing America up for war against Saddam Hussain and Iraq, Penn accepted an invitation from the Institute of Public Accuracy to visit Baghdad. He did not, he said, accept the government's spin on the situation and was following EL Doctorow's advice that it is "the responsibility of the artist to know the time in which he lives". So, over he went, visiting hospitals, schools, poor neighbourhoods and the Iraqi Foreign Minister's office, returning to the US to report on his findings. This he did by paying $56,000 for a page of the Washington Post, printing an open letter to Bush, asking him, as the father of two and as the son of a WW2 veteran, to slow the march to war.
Thus Penn became the public face of a much frowned-upon anti-war movement, for which most newspapers attacked him mercilessly. Just as Jane Fonda had become known as Hanoi Jane during Vietnam, so Penn became Baghdad Sean, venomously accused of undermining American solidarity in a time of crisis. It didn't help when the Iraqi government's news agency claimed that he had confirmed there were no weapons of mass destruction in the country, thereby forcing Penn to admit that he'd been used by Saddam Hussein.
Undeterred, Penn would return to Iraq in late 2003, writing a long article for the San Francisco Chronicle about the problems of both the people and the coalition forces. He'd also taken another page in a national paper, this time the New York Times, to publish a 4000-word essay on the subject, noting "the repressive condition of public debate in our country, as it prepared for war". In this he must have been mindful of his own father's blacklisting, all those years before.
There would be further repercussions, and alleged blacklisting, when Penn left the set of Why Men Shouldn't Marry, produced by Steve Bing. Penn claimed he'd been sacked due to the Iraq furore, particularly after his public questioning of the invasion on the Larry King Show. Bing retorted that Penn had attempted to blackmail him with a potentially damaging audio tape, a claim that was kicked out of court. The suing and counter-suing for tens of millions would stretch on into 2004.
When Penn collaborated on a multinational impressionistic documentary on the September 11th attacks - he directed a 10-minute film as the US contribution, Ken Loach delivering for the UK and Alejandro Gonzalez Inarritu for Mexico - it seemed politics were now dominating his career. But all the while, working on a punishing schedule, he'd been continuing to act.
Aside from This So-Called Disaster, a documentary by Michael Almereyda on that aforementioned production of The Late Henry Moss, the first result of this was It's All About Love, a sci-fi contemplation of love and life by Danish Dogme director Thomas Vinterberg so strange it had trouble finding a distributor. Here Joaquin Phoenix and Claire Danes played a Polish couple who, while in the process of divorce in 2021, are drawn back to each other by freaky conditions. Sub-zero temperatures arrive for just a few minutes, gravity fails to do its job in Uganda, and all the unloved people in New York are dying in the streets. Meanwhile, up above them, Penn played Phoenix's brother, a man who has sought therapy and medication to combat his fear of flying and is now afraid to STOP flying. As said, it was a real oddity - philosophical, action-packed, and impressive way beyond its $10 million budget - very much a Sean Penn kind of movie.
He moved on to a series of performances quite exceptional even by his now lofty standards. 2004 brought Clint Eastwood's Mystic River (Eastwood having earlier approached Penn to appear in his 2002 thriller Blood Work), where Penn, Kevin Bacon and Tim Robbins played three childhood friends scarred by an abduction and molestation. As adults, they are reunited by the murder of shopkeeper Penn's daughter, a crime to be investigated by cop Bacon, with Robbins, who returned to his house covered in blood on the night of the murder, one of the chief suspects. Penn was tremendous as a father jealously guarding his daughter, then aggressively seeking revenge for her death, his hatred, suspicion and barely controlled violence created much of the film's tension. He'd deservedly win a Golden Globe and an Oscar, surprisingly turning up to accept the latter after years of refusing to attend the ceremony.
He'd find further critical success with his next picture 21 Grams, directed by his 9/11 documentary peer Inarritu, renowned for his Amores Perros. Near unrecognisable from his Mystic River character, here Penn played an impressionable good-guy maths professor who's dying from a heart condition and being pestered by wife Charlotte Gainsbourg into donating sperm so she can have his baby (perhaps when he's dead). Meanwhile, Naomi Watts played a recovering addict, as did Benicio Del Toro, though Del Toro had substituted drugs and booze for repressive control over his family. As the action cut stylishly back and forth through time, the lives of the three main protagonists were pulled painfully together by a single tragic event. Rarely nominating anyone twice in the same year, the Academy would ignore Penn's fine performance, though the British Academy would nominate him for both Mystic River and 21 Grams.
Following this, there'd be The Assassination Of Richard Nixon, originally titled Killing Dick. Directed by Niels Mueller, hot after the sophisticated coming-of-age comedy Tadpole, this told the true-life tale of Samuel Byck who, in February 1974, failed in an attempt to top the President. Reuniting with Naomi Watts, this time playing his estranged wife, Penn had a challenge on his hands to portray this insecure, lonely, angry man as he loses his wife and kids, gets bullied and patronised at work and is refused a grant to start his own business, eventually turning his resentment towards his country's leader. Being a sort of comedy Taxi Driver (at one point Byck attempted to join the Black Panthers), the film would walk a difficult line and, of course, Byck's plot to hijack a plane at Atlanta and fly it into the White House carried a new and unpleasant weight in the wake of September 11th. It was risky - again, very Sean Penn.
Penn would return to the world of international politics with his next outing, Sydney Pollack's The Interpreter. Here Nicole Kidman would play the titular interpreter, a South African working at the United Nations when she overhears a plan to murder an African leader. She goes to the FBI, Penn playing an agent who's first sceptical then convinced as he tries to both protect her and foil the dastardly scheme. Back in the real world, 2005 would also see New Orleans devastated by Hurricane Katrina, a disaster made all the worse by the American government's painful failure to act. After three days watching the catastrophe unfold on TV, Penn could no longer stand the suffering and, risking almighty public ridicule, he flew to New Orleans, procured a boat and set about rescuing people from their flooded dwellings, much of the time armed with a shot-gun. The papers, as ever, were cruel, mocking Penn's efforts as silly and attention-seeking. Yet attention was clearly what Penn was after. He wanted his country to see what was going on and, more particularly in the case of the Bush administration, what was not going on. Beyond this, it was reported that he did ferry some 40 people to safety.
2006 would be another challenging year. Onscreen he'd star in a remake of the 1949 Oscar winner All The King's Men, based on the rise and fall of Huey Long in Louisiana. Here Penn would play the yokel Willie Stark, picked to run for governor in order to split the hick vote. Recognising the devious plan, he gets serious and discovers a talent for politics and fiery oratory, talking to the people on their own level, attacking the corruption and cronyism of the rich establishment. As the years pass, though, he's corrupted himself, his career coming to a head when he attempts to cover up a building scam by blackmailing the upstanding judge - Anthony Hopkins - who's aiming to bring him down. It was a wild performance by Penn, full-blown and even hammy as he searched for Stark's popular appeal. The movie, though, despite a starry cast also including Jude Law and Kate Winslet, would tank. This disappointment, however, was nothing compared to the loss Penn suffered the same year when his brother Chris died at the age of just 40. Due to drug use his heart had over-enlarged. Chris had never risen to the artistic heights of his brother Sean but he had, in movies such as The Funeral, shown exceptional talent and emotional range. It was a sad loss for all.
The next year would see more personal turmoil when, after eleven years of marriage, Robin Wright Penn filed for divorce. Irreconcilable differences were mentioned, but they couldn't have been as irreconcilable as all that, as the couple would indeed reconcile, withdrawing the divorce petition in April, 2008. In the meantime, Sean had lent his voice to the English version of Persepolis, the animated film adaptation of Marjane Satrapi's autobiographical graphic novels. Here we'd see Satrapi as a precocious girl in pre-Revolutionary Iran, loving pop music and fashion, then forced to cover her face and deny her feelings as the Ayatollah takes over. Shipped to Vienna, she finds western decadence too much and must return to the strictures of home. It was thoughtful, moving and informative, Penn territory, of course. So, too, was Into The Wild, Penn's latest directorial effort. This told the real-life tale of Christopher McCandless, a young man who turned his back on a good life and career and took off, first onto the road, then into the Alaskan wilderness where, despite knowing little of woodcraft, he survived for over three months before dying. Penn, taken by McCandless's total and fatal refusal to play the game, spent ten years persuading the lad's family to let him make the picture. It turned out to be a beautiful portrait of the American landscape, and of one man's courage and determination.
Beyond filming, Penn was still very much a political activist. Like McCandless refusing to blindly follow accepted opinion, in 2007 he'd visit Venezuela, spending several hours with president Hugo Chavez, a sworn enemy of American imperialism. Back in America Penn would risk more ridicule by appearing on The Colbert Report, taking on Stephen Colbert in debate and thrashing him. The following year would see him outside the mainstream yet again as he'd back the progressive democratic candidate Dennis Kucinich in the presidential election. He'd then court yet more controversy by visiting Cuba and meeting another of his country's sworn enemies, Raul Castro.
Professionally, 2008 would be a great year for Penn. Not only did he stand as president of the jury at the Cannes Film Festival, he also scored another artistic hit with Milk. Directed by Gus Van Sant, and co-starring Josh Brolin and Emile Hirsh (who'd recently played Christopher McCandless for Penn), this would see Penn as the famed homosexual freedom fighter Harvey Milk. Coming out of the closet at 40 and changing his life around, in the 1970s Milk would move to San Francisco where, witnessing the harsh treatment dealt out to homosexuals by the police, he'd decide to influence events by running for the Board of Supervisors, becoming the first openly gay man to win office in America. Penn would play Milk as funny and flawed, smart and idealistic, an Ordinary Joe who decides enough is enough and makes things better through the force of his own will - a real beacon of hope. His performance would be feted everywhere, winning him another Oscar and nominations for a Golden Globe and BAFTA.
2009 would bring yet more variety. First would come Crossing Over, a Traffic-like multi-story piece dealing with immigrants in Los Angeles, covering people-smuggling, document fraud, the asylum and naturalization processes, counter-terrorism and culture clashes. One plot-line would see Ashley Judd attempt to adopt a Nigerian girl, another would see her husband, Ray Liotta, grant a via to an Aussie girl in return for sex. Meanwhile INS agent Harrison Ford is begged to help a Mexican boy, while his partner, who has an Iranian background, has his sister murdered in an honour killing. Penn himself would appear in a brief cameo as a border patrol guard who crashes his car in the desert at night. Badly injured , he's comforted by a Mexican woman trying to sneak across the border. They show each other photos of their kids, find a common language, only for the woman to be raped and murdered by coyotes - vicious people-smugglers operating in the outback. Penn's was, as said, as brief role, but he had plenty of involvement in the picture. Upset by the way director Wayne Kramer dealt with the honour killing, he asked to be cut from the film, or have his name removed. Penn, along with Ford, would also be allowed to edit versions of the movie by producer Harvey Weinstein, who was unhappy with Kramer's initial cut. Shot in the spring and early summer of 2007, the film would take two years to come to the screen.
Even then, Crossing Over had a shorter gestation period than Penn's next film, The Tree Of Life, which director Terrence Malick had worked on for 30 years. Also starring Brad Pitt, this would follow a young mid-Western kid from innocence to disillusion, the world over the years turning from a thing of wonder to a malevolent puzzle. Penn would play the kid's older self, a lost soul seeking the unchanging realities of life and rediscovering his earlier sense of joy.
Back in the late Nineties, the man once described by the New York Times as "both a human tempest and an actor of sizeable gifts" seemed to be going more quietly. The tattoo on his left forearm that reads "Deliver me" in gothic script didn't carry the weight it did in his enraged and outraged youth. After Iraq, that changed. His move, with his wife and children, to Marin County, in the Bay Area of the ever-politicised San Francisco, may have revitalised him, for the new millennium brought a rekindled desire to fight the good fight, even at the risk of facing his blacklisted father's cruel fate.
There can be no doubt that he will stick his neck out time and again. And he will be an increasingly excellent and valuable movie-maker for years to come, surely winning more Oscars both as director and actor. As said, the man's gifts are sizeable.