The many faces of Sean Penn

How the controversial actor went from stoner to award winner

He’s played stoners and drug dealers, men who have watched loved ones die and men who are dying themselves. And through it all there’s always an inviting intensity to Sean Penn—something irresistible about him, even as he’s operating at the extremes.

He’s generating major Oscar buzz for his performance as Harvey Milk, California’s first openly gay elected official who was assassinated in 1978, in Gus Van Sant’s “Milk.” Penn embraces both the triumphant and tragic nature of the influential San Francisco supervisor, chalking up yet another unforgettable character.

Here’s a look at nine other highlights from 25 years worth of Penn performances.  —S. James Snyder, Special to Metromix