One afternoon in January, Sean Penn answers the door of his Bay Area home, shoeless, in jeans and a gray thermal undershirt, his hair sort of crazily mussed, looking as if he’s just woken up. It’s a couple of minutes past noon. To say that Penn has “aged well” is to employ a nonstandard usage of the term. He does not look younger than his 48 years. His forehead is baroquely creased, his long face haggard, his hair soaring and gray-streaked and parted down the middle. Something Penn is wearing, or Penn himself, exudes a beer-and-cigarettes musk particular to the morning after a rough night. All of which sounds like the opposite of a compliment, and for many it would be — but Penn has aged into exactly the type of guy he’s always seemed to want to be. When he was younger, not yet anointed the greatest actor of his generation, Penn had a habit of befriending older men he’d long idolized (Jack Nicholson, Charles Bukowski, Dennis Hopper, Hunter S. Thompson) who had, aside from their obvious talents, seemed to figure out a way of living (a way of living very hard) that also became an integral extension of their art. Like the brilliant character actor that he is, Penn studied these men and lived hard himself — fistfights, benders, jail, Madonna, public references to a sitting president’s “soiled and blood-stained underwear.” “I’m not an alcoholic,” he told The New York Times Magazine in 1998. “I’m just a big drinker, and there’s a difference.” You get the sense that Penn would welcome, somewhere down the road, a Bukowski-esque level of physical decay.
Inside the house, Penn’s daughter, Dylan, 17, and a friend are preparing food in the kitchen, where a holiday card from the Coppolas (Francis Ford and wife pictured on the front) hangs on the wall. A massive stone fireplace dominates the living room. (If there is not such a thing as a walk-in fireplace, the term should be invented for this one.) Son Hopper, 15, is nowhere to be seen. In another room, there’s a framed poster of a film noir called Fall Guy, which starred Penn’s father, Leo, an actor and director who was blacklisted in the Forties and Fifties. (To bypass the blacklist, Leo Penn was billed in Fall Guy as “Clifford Penn.”)
Sean Penn has just been nominated for Best Actor for his title role in Milk, Gus Van Sant’s triumphant biopic about the pioneering gay politician Harvey Milk, who in 1978 was assassinated, along with the mayor of San Francisco, by a deranged city supervisor (played in the film by Josh Brolin). It’s another virtuosic performance by Penn, who has amassed nearly 30 years’ worth of them — beginning with Jeff Spicoli in Fast Times at Ridgemont High, one of the few Penn characters, incidentally, who comes to a good end. (And even he blows all of the reward money he gets from rescuing Brooke Shields from drowning by hiring Van Halen to play at his birthday party.) Post-Fast Times, Penn has starred in exactly three comedies: the forgotten Crackers; the excellent, bittersweet Woody Allen movie Sweet and Lowdown, in which Penn plays a 1930s jazz guitarist; and the Robert DeNiro buddy flick We’re No Angels. “I like doing comedies,” Penn says, not smiling, “but I’m not the first guy they go to on that shit.” No, Penn’s IMDb page is mostly bad news: juvie (Bad Boys), death row (Dead Man Walking), war crimes (Casualties of War), murdered daughters (Mystic River), unsuccessful heart transplants (21 Grams), cokehead amateur spies (The Falcon and the Snowman), cokehead Hollywood bottom-feeders (Hurlyburly), cokehead mob lawyers with very bad hair (Carlito’s Way), psychotic fathers played by Christopher Walken (At Close Range) and next up — for director Terrence Malick — the troubled son of a troubled Brad Pitt (The Tree of Life). Which makes Penn’s utter transformation into Milk, a charismatic, unflaggingly positive grassroots activist, all the more remarkable. What’s most surprising is not the fact that Penn is so good at playing a proudly out gay man — it’s that he’s so good at playing such a nice guy. As his friend Brolin (half-) joked in a speech at the New York Film Critics Circle awards, “We’ve known Sean as an actor who doesn’t smile very much. And the fact that you smiled as much as you did in this film is amazing. Truly incredible. You are going to get the Oscar. Because you smiled so much.”
Penn and I spend about five hours together over the course of two days. A decent amount of the time, we drive around Marin County in my ridiculous rental car, a tiny, bright-red convertible. Penn rides shotgun, smoking, sunk low in the seat, often forgetting to give me directions until the last minute, then seeming pleased when I’m forced to cut off other cars or ubiquitous cyclists. (Penn: “Do you ride a bike?” Me: “No.” Penn: “Good.”) When not in character as Harvey Milk, Penn is not exactly generous with those broad smiles. His blue eyes constantly seem to be peering at you over a pair of reading glasses, even when he is not wearing reading glasses, which gives him a perpetually skeptical air. But despite his reputation (moody, hates journalists), Penn is an easy man to get along with. One day at brunch, we’re joined by his wife, the beautiful actress Robin Wright Penn. The next day, we drive out to a Puerto Rican chicken place in San Rafael that Penn loves, taking an outdoor table near the parking lot.