Long the bad boy of Hollywood, Sean Penn is also among the most fiercely talented actors of his generation. He was born August 17, 1960, in Burbank, CA, 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 singer/songwriter-turned- director, 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 stole every scene in which he appeared, helping to elevate the picture into 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 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.