Oprah and Sean Penn
Photo: Rob Howard
One of America's finest, grittiest actors—and an Oscar winner for Mystic River—lets down his legendary guard to talk about acting, patriotism, his short-lived marriage to Madonna, his bad-boy reputation, his envelope-pushing film, The Assassination of Richard Nixon, and why he remains optimistic about our nation's future.
Two paces away from the red velvet couch where Sean Penn sits to smoke and read scripts, a framed photo captures the moment at last year's Oscars when he stood before an audience of his peers, all on their feet applauding. His Best Actor win (for Mystic River ) was one victory; finding the courage to show up for his first Academy Awards ceremony—despite three previous nominations—was another.

People don't usually think of Sean Penn as reclusive. His reputation is as a rebel: the guy who fired a handgun at helicopters the day he married Madonna in 1985, picked fights in bars, struck a photographer, and landed himself in jail in 1987. More recently, his political activism—he took out full-page antiwar ads in the Washington Post and later The New York Times —has drawn as much attention (a lot of it critical) as his starring roles in films such as Dead Man Walking (1995), Hurlyburly (1998), and I Am Sam (2001).

Yet for all the headlines, he rarely gives interviews. So when he agreed to let me talk with him at the home he shares with his wife, actress Robin Wright Penn, and their two children just outside of San Francisco, I was jumping up and down with excitement. Right before our conversation, I watched his film, The Assassination of Richard Nixon , based on the true story of Sam Byck, who planned to kill the president in 1974 by hijacking a plane and crashing it into the White House. Penn's performance as Byck is one of his most provocative. When I finally sit across from the actor, I find a man who couldn't be more different from the way he's been labeled.

Start reading Oprah's interview with Sean Penn

Note: This interview appeared in the January 2005 issue of O, The Oprah Magazine.

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