Penn, 48, who won the Oscars best actor award for his performance as a trailblazing gay politician in “Milk,” has seen his stock rise since the mid-1990s, with his second Academy Award following the 2003 “Mystic River.”
“Milk” director Gus Van Sant, who describes Penn as “the Brando of our generation,” said the actor was his first choice for the role.
The film’s screenwriter Dustin Lance Black said Penn’s performance was uncannily realistic. “I don’t know how he did it,” Black said. “Sean physically inhabited the body and soul of Harvey Milk.”
It was the latest milestone in a glittering career for Penn, a member of the 1980s “brat pack” who, despite great success and critical acclaim, remains firmly entrenched as a Hollywood outsider.
Only last year, Penn appeared to disparage the Oscars in an interview with French daily Le Monde, describing the awards seasons highlight as a place “where manipulation and very good marketing are rewarded.”
Penn’s disdain for playing the marketing game is legendary; he rarely grants interviews and was a noticeable absentee at last month’s Golden Globes.
As Penn’s career has flourished he has also become a vocal political activist, enraging conservative pundits in the United States for his criticism of former president George W. Bush, who he has said should be impeached.
He was lambasted for visiting Iraq in December 2002, which came two months after he paid 56,000 dollars for an advertisement in the Washington Post protesting Bush’s “war on terror” and planned invasion of Iraq.
Penn has also reportedly developed a friendship with Venezuelan President Hugo Chavez, another bete-noire of the Bush administration.
Born in August 1960 in Los Angeles to director Leo Penn and actress Eileen Ryan, Penn grew up in the industry that he has so often infuriated by refusing to play its game and abandoned his dream of being a lawyer to study acting.
In 1981 he made his Broadway debut in the play “Heartland” and his movie debut as a military cadet in “Taps” (1981). He won some fame as a “surfer dude” in Amy Heckerling’s 1982 hit teen flick “Fast Times at Ridgemont High.”
But it was not his acting that propelled him to global celebrity, but his 1985 marriage to “Material Girl” Madonna, with whom he co-starred in the universally-panned 1986 mega-flop “Shanghai Surprise.”
After four years of turbulent marriage, during which he served 32 days in jail in 1987 for hitting a movie extra, the pair divorced, leaving Penn’s talent overshadowed by his tempestuous outbursts and superstar ex-wife.
He then took starring roles in films such as “Colors” (1988) opposite Richard Dreyfuss, as a brutal sergeant in Brian de Palma’s “Casualties of War” (1989) and in the 1989 comedy “We’re no Angels” with Robert De Niro.
In 1991 his made his directorial debut with “The Indian Runner,” an impressive Vietnam War-themed drama inspired by a Bruce Springsteen song.
Penn appeared as a reptilian lawyer in the 1993 thriller “Carlito’s Way,” before saying he was retiring from acting to direct, and then making the 1995 “The Crossing Guard” with Jack Nicholson and Anjelica Huston.
In 1995 he was lured back to the screen by friend Tim Robbins, only to win his first Oscar nomination for the death row tale “Dead Man Walking.”
As his bad boy image began to wear off, he garnered two more Academy Award nods for “Sweet and Lowdown” (1999) and for his role as a mentally-handicapped father in 2001’s “I am Sam.”
Since the beginning of the 1990s, Penn has been with his second wife, “Forest Gump” actress Robin Wright Penn, with whom he has two children.
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