The stoner surfer Spicoli grew into a three-time Oscar winner
Sean Penn's Jeff Spicoli in Fast Times at Ridgemont High helped make "dude" part of everyday speech. The same actor went on to collect Best Actor Oscars for Mystic River and Milk, and a supporting award for One Battle After Another. He also hired the real convicted spy he once portrayed as his assistant.
Penn was born in Santa Monica on August 17, 1960, to the director Leo Penn and the actress Eileen Ryan. His brothers are the musician Michael Penn and the late actor Chris Penn. He grew up in a secular household in Malibu, where he made home movies with neighbours Emilio Estevez and Charlie Sheen. His first screen moment was as an extra in a 1974 episode of Little House on the Prairie, which his father was directing.
His film career opened in 1981 with Taps, as a military school cadet, and the same year he debuted on Broadway in Heartland. After Spicoli, the reform-school drama Bad Boys got him taken seriously. In The Falcon and the Snowman he played Andrew Daulton Lee, a former drug dealer jailed for spying for the Soviet Union. When Lee was paroled in 1998, Penn gave him a job, partly as thanks and partly because he believed in rehabilitation.
Frustrated with the industry, he stepped back from acting in the early 1990s to direct. The Indian Runner, his 1991 debut, grew out of a Bruce Springsteen song, Highway Patrolman. He came back as Al Pacino's crooked lawyer in Carlito's Way, and then played a racist killer awaiting execution in Dead Man Walking, which Roger Ebert said proved him the most powerful actor of his generation. She's So Lovely won him the acting prize at Cannes, and Hurlyburly the Volpi Cup at Venice.
Oscar nominations followed for Sweet and Lowdown, as a vain jazz guitarist, and I Am Sam. The first win came with Clint Eastwood's Mystic River in 2003, as a father searching for his daughter; the second for Gus Van Sant's Milk, about the gay rights campaigner Harvey Milk. Behind the camera, Into the Wild (2007) earned him a Directors Guild nomination. Not everything landed: in 2010 Forbes named his 2006 film All the King's Men the worst flop of the previous five years.
Source: Sean Penn
