Actor, writer, director, producer. Born August 17, 1960, in Burbank, California. Penn grew up in Los Angeles and attended Santa Monica High School, along with fellow students and future actors Emilio Estevez, Charlie Sheen, and Rob Lowe. An early interest in filmmaking, specifically directing, led to a passion for acting, and Penn moved to New York City when he was 19 to pursue a career as an actor. He soon landed a part in a Broadway play, Heartland. In 1981, he made his film debut, in the military school drama Taps, alongside star Timothy Hutton (already an Oscar-winner for 1980’s Ordinary People) and fellow up-and-comer Tom Cruise.
Penn’s breakthrough role came a year later, when he played perpetually stoned surfer Jeff Spicoli in the high school comedy Fast Times at Ridgemont High. He garnered acclaim for his first starring role, in 1983’s Bad Boys and for The Falcon and the Snowman (1985), also starring Hutton. In 1985, Penn gained a whole new measure of fame when he married pop goddess Madonna. Their tumultuous four year marriage produced one dismal movie, 1986’s Shanghai Surprise, and a barrage of tabloid headlines. Penn’s “bad boy” image only increased with his continued hostility towards the aggressive paparazzi—he served 34 days in prison in 1987 for punching an extra who had tried to take his picture on the set of the film Colors, co-starring Robert Duvall and directed by Dennis Hopper. Penn and Madonna divorced in 1989.

In 1991, two years after earning rave reviews for his performance in Casualties of War (1989), directed by Brian De Palma and co-starring Michael J. Fox, Penn directed his first film, the little seen feature The Indian Runner. Though he had claimed he was quitting acting, Penn was back in front of the camera in 1993, playing a coke-addled criminal lawyer in De Palma’s Carlito’s Way, co-starring Al Pacino. In 1995, he starred as a death row inmate searching for salvation in the critical and popular success Dead Man Walking, directed by Tim Robbins and co-starring Susan Sarandon. Penn’s powerful performance earned him his first Academy Award nomination, for Best Actor. That same year, he wrote, produced, and directed The Crossing Guard, a dark drama starring his boyhood idol, Jack Nicholson.