Sean Penn

Hailed as one of the finest actors of his generation, Sean Penn earned multiple Oscar nominations for his onscreen intensity and proved a powerful filmmaking talent at the helm of his own character-driven dramas like "The Crossing Guard" (1995) and "The Pledge" (2001) - all the while remaining the ultimate Hollywood outsider. Penn originally broke through with his iconic turn as stoned surfer Jeff Spicoli in "Fast Times at Ridgemont High" (1982), but he established himself as a serious actor with "Bad Boys" (1983), only to be hounded by paparazzi due to his high-profile, short-lived marriage to Madonna, which resulted in the box-office dud "Shanghai Surprise" (1985) and violent run-ins with photographers. He entered a long and slightly less turbulent marriage to Robin Wright, while earning acclaim as a smarmy lawyer in "Carlito's Way" (1993) and a death row inmate in "Dead Man Walking" (1995). After "Sweet and Lowdown" (1999) and "I Am Sam" (2001), Penn won the Oscar for his portrayal of a streetwise father out to avenge his daughter's murder in "Mystic River" (2003). Meanwhile, he traded his bad-boy persona for political outspokenness, which included calling for the impeachment of President Bush while rankling conservatives for hobnobbing with reviled world leaders. Still, Penn continued to deliver onscreen with "Milk" (2008), though his refusal to play the Hollywood game earned him an unshakable reputation as hostile and arrogant. Despite such opinions, no one could deny that Penn's work was consistently of the highest caliber, making him a modern-day Marlon Brando.