Sean Penn: The Rolling Stone Interview

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 De Niro 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 grass-roots 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.

One thing Penn doesn't want to discuss much is politics. But the topic is inevitable: After he wrote an article for The Nation on his visits with Venezuelan president Hugo Chávez and Cuban president Raúl Castro — a longer version appeared on The Huffington Post — he was scolded by a chorus of journalists as being fawning and hopelessly naive. Penn, of course, gives as good as he gets. At one point in our interview, railing about the lack of commitment displayed by some of his acting peers, he says, "People are spending too much time modeling for some fucking clothing company instead of acting, and I resent it. It's like, 'I'm sorry — are you going to do the Chanel ad today? I thought you were in the middle of shooting a fucking movie.'

"You see wonderfully talented actors everywhere, which almost makes it sadder," Penn says wearily, lighting another American Spirit. "It's not about what kind of movies they make. I don't care if they make love stories — there are great love stories. Just let me know you mean it. I want to know you're trying to write the Great American Novel every time. Fail all you want. But fucking try."