He has been awarded, among others, two Oscars for his performance in the films Mystic River (2003) and Milk (2008). He made his directorial debut in 1991 with the film The Indian Runner, followed by the dramas The Crossing Guard and The Pledge, both starring Jack Nicholson. His fourth feature film, Into the Wild, was critically acclaimed and received two Oscar nominations.
He began his acting career with a brief appearance in an episode directed by his father Leo Penn on the television series The Ingalls Family. During the 1980s, he played a variety of roles in films such as Fast Times at Ridgemont High or Bad Boys, among others. Thanks to his performance in the Brian de Palma-directed film Carlito's Way (1993), he garnered critical attention and began to stand out as an actor thanks to his role as sentenced to death in Dead Man Walking (1995) alongside Susan Sarandon, being nominated for the first time for the Oscar for best actor.
In addition to his work in film, he is known for his political and social activism, especially for his criticism of the Bush Administration, his friendship with the presidents of Venezuela and Cuba, as well as for his humanitarian work in the aftermath of Hurricane Katrina in 2005. and the 2010 Haiti earthquake. He also attracted media attention due to his previous marriages to singer Madonna and actress Robin Wright, with whom he has two children.
Along with his up-front philanthropy, he has also is consistently the center of controversy. He has had many tumultuous relationships where he admits abusive behavior towards the women in his life and getting involved in controversial figures like Hugo Chávez and "El Chapo" and taking advantage of smaller creators and going on aggressive rampages against staff members of his. He's also been called out for racist and offensive comments.