Sean Penn

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.

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 to eclipse even 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, as the couple's star collaboration in the 1987 movie Shanghai Surprise met with box-office disaster, their private relationship was also over. 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 De Niro, 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 and shaped in the image of the films of John Cassavetes. After an almost unrecognizable turn as a troubled attorney in the 1993 DePalma thriller Carlito's Way, Penn announced his intention to retire from acting in order to focus his full attentions on directing; however, after helming 1995's The Crossing Guard with Jack Nicholson and Anjelica Huston, he was back onscreen, 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. He found further acclaim the following year for his roles in the adaptation of David Rabe's Hurlyburly and Terrence Malick's The Thin Red Line. In 1999, he had a cameo appearance in Spike Jonze's Being John Malkovich and earned his second Oscar nomination as a callous '30s jazz guitarist in Woody Allen's Sweet and Lowdown, while 2000s adaptation of Anita Shreve's novel, The Weight of Water, starred Penn as a poet embroiled in a small town murder mystery. In 2001, Penn would play a fame-craving impressionist in The Beaver Trilogy, serve as narrator in director Stacy Peralta's skateboarding documentary Dogtown and Z-Boys, and direct the psychological drama The Pledge, which marked Penn's second collaboration with Jack Nicholson. In 2002, Penn would once again win critical praise with his Oscar-nominated portrayal of a developmentally disabled man struggling to retain custody of his daughter in I Am Sam.

After the 2001 terrorist attacks on the World Trade Center and Pentagon, the left-leaning actor's outspoken political views garnered a great deal of attention from right-wing pundits, including the much aggrieved Bill O'Reilly, who found himself on the receiving end of Penn's animosity in a controversial interview with ~Talk magazine. Though O'Reilly demanded his viewers boycott any of Penn's future films, it appears his career has remained relatively unscathed. In 2002, Penn directed a segment for the French-produced