Long the bad boy of Hollywood, Sean Penn was also among the most fiercely talented actors of his generation. He was born August 17, 1960 in Burbank, California. The second son of actress Eileen Ryan and director Leo Penn, he grew up in Santa Monica, in a neighborhood populated by future celebrities Charlie Sheen and Emilio Estevez, the sons of actor Martin Sheen. Penn's older brother Michael is a successful pop singer/songwriter, while younger sibling Chris is a noted character actor. The children spent much of their free time together, making a number of amateur films shot with Super-8 cameras. Still, Penn's original intention was to attend law school, although he ultimately skipped college to join the Los Angeles Repertory Theater. After making his professional debut on an episode of television's Barnaby Jones, he relocated to New York, where he soon appeared in the play Heartland. A TV-movie, The Killing of Randy Webster, followed in 1981 before he made his feature debut later that same year in Taps.

Penn shot to stardom with 1982's Fast Times at Ridgemont High; as the stoned surfer dude Jeff Spicoli, he easily stole every scene in which he appeared, helping elevate the picture far beyond its competition to become a classic of the teen comedy genre. However, the quirkiness which would define his career quickly surfaced as he turned down any number of Spicoli-like roles to star in the 1983 prison drama Bad Boys, followed a year later by the Louis Malle caper comedy Crackers and the period romance Racing With the Moon. While none of the pictures performed well at the box office, critics consistently praised Penn's depth as an actor. A turn as a drug-addict-turned-government spy in John Schlesinger's 1985 political thriller The Falcon and the Snowman earned some of his best notices to date, but Penn's performance was quickly lost in the glare of the media attention surrounding his very public romance with pop singer Madonna, which culminated in the couple's 1985 media-circus wedding.

While Madonna actively courted press attention, the private Penn made his loathing for the media quite clear; his run-ins with the paparazzi quickly became the stuff of legend, and the notoriety of his temper began even to eclipse his immense acting ability. His penchant for fisticuffs, combined with other civil infractions, ultimately resulted in a 30-day jail sentence; more seriously, his marriage to Madonna began to buckle under the weight of media scrutiny, and when the couple's star collaboration in the 1987 movie Shanghai Surprise met with box-office disaster, their relationship was essentially finished. Soured by the Hollywood experience, Penn did not resurface prior to 1988's Colors, which proved to be his biggest hit in some time. He next appeared in Brian DePalma's Vietnam tale Casualties of War, followed by a turn opposite his idol, Robert DeNiro, in the 1989 comedy We're No Angels.

After starring in the gangster melodrama State of Grace, Penn wrote and directed 1991's The Indian Runner, a film inspired by a Bruce Springsteen song. After an almost unrecognizable turn as a troubled attorney in the 1993 DePalma thriller Carlito's Way, Penn announced his intentions to retire from acting in order to focus his full attentions on directing; however, upon helming 1995's critically-acclaimed The Crossing Guard he was back on-screen, winning an Academy Award nomination for his gut-wrenching portrayal of a death-row inmate in Tim Robbins' Dead Man Walking. By 1997, Penn's wishes for retirement were but a memory as he enjoyed his busiest year yet: in addition to starring opposite second wife Robin Wright in Nick Cassavetes' She's So Lovely -- roles which won both spouses acting honors at the Cannes Film Festival -- he also appeared in the David Fincher thriller The Game and in Oliver Stone's U-Turn.