He rose to fame as the star of Fast Times at Ridgemont High. His role in the 2003 film, Mystic River, earned him an Academy Award and a Screen Actors Guild Award.
He won an Academy Award for Milk, and directed the film Into the Wild.
He dedicated his film The Crossing Guard to Charles Bukowski.
His childhood friends included actors Charlie Sheen and Emilio Estevez, whom he created short films with. He started his career by appearing in a 1974 episode of Little House on the Prairie.
He married pop star and actress Madonna in 1985. Their relationship ended in 1989. He later married actress Robin Wright, but divorced her in 2010. In 2014, he began dating actress Charlize Theron. He has a son named Hopper and a daughter named Dylan.
- The meaning of the name Penn: Lives By The Hill