Sean Penn began his early acting career in films such as Taps and Fast Times at Ridgemont High in the early 1980s. In 1986 he starred in At Close Range with Christopher Walken. He has been nominated for Best Actor at the Academy Awards five times, and has won the award twice.
Following his film debut in Taps and a diverse range of film roles in the 1980s, Penn subsequently emerged as a prominent leading actor with the 1995 drama film Dead Man Walking, for which he earned his first Academy Award nomination and the Best Actor Award at the Berlin Film Festival. Penn subsequently received another two Oscar nominations for Sweet and Lowdown and I Am Sam, before winning his first Academy Award for Best Actor in 2003 for Mystic River and a second one in 2008 for Milk. He has also won a Best Actor Award of the Cannes Film Festival for She's So Lovely, and two Best Actor Awards at the Venice Film Festival for Hurlyburly and 21 Grams.
Penn made his feature film directorial debut with The Indian Runner, followed by the drama film The Crossing Guard and the mystery film The Pledge (2001). In 2002, Penn directed one of the 11 segments of 11'09"01 September 11, a compilation film made in response to the September 11th attacks. In 2007, Penn directed his fourth feature film Into the Wild, which garnered critical acclaim and two Academy Award nominations.