Soon thereafter, his turn as pothead surfer Joe Spicolo in Fast Times at Ridgemont High (1982) made him an overnight sensation. His next project was 1983's disturbingly violent prison drama Bad Boys, followed by Crackers (1984) and the WWII-era Racing with the Moon (1984). While the latter was not a box office hit, Penn got great reviews for playing a young man on the verge of shipping out. Then, according to the critics, Penn outdid himself again in the espionage thriller The Falcon and the Snowman (1985).

After his tumultuous marriage to and divorce from Madonna, which included his infamous roughing up of the paparazzi and the disappointment of Shanghai Surprise (1987), Penn would resurface with Colors (1988), a timely, riveting story set in L.A.'s gang-ridden neighborhoods. Sean Penn the actor has at times stepped aside for Sean Penn the director. His films to date include The Indian Runner (1991), The Crossing Guard (1995) and The Pledge (2001); Penn's directorial efforts are light on action but heavy on the emotion, with actors given plenty of room to flex their thespian muscles.

It was for 1995's Dead Man Walking that Sean Penn received an Academy Award® nomination for Best Actor. Though he did not win, his performance as a racist, hate-filled death row inmate was brave and heartrending. Then would come celebrated turns in 1997's She's So Lovely alongside wife Robin Wright Penn, Hurlyburly (1998), The Thin Red Line (1998) and Woody Allen's Sweet and Lowdown (1999). In 2002, he received his second Best Actor Oscar® nod, for I Am Sam, in which he played a mentally-handicapped man fighting for custody of his daughter. His latest outing was in Mystic River (2003), a Clint Eastwood drama set in Boston.