5 Most Prolific Actors turned Directors gallery 2010 Sean Penn
Sean Penn: His work both in front of and behind the camera keeps getting better. In 2007, he directed "Into the Wild," a devastating look at the meaning of survival featuring a killer performance from Emile Hirsch; the next year, he starred as slain gay rights leader Harvey Milk in "Milk," and won his second best-actor Oscar. One of the hallmarks of the films Penn has directed -- including 1995's "The Crossing Guard" and 2001's "The Pledge," both with Jack Nicholson -- is that he never shies away from the bleaker aspects of the story. It's as if he's taken his own formidable ability to portray the raw humanity of his characters and honed it into a similar intensity when he directs others. And in doing so, he's truly found the best of both worlds.