This e-single follows the career and life of Sean Penn from 1981 to 2012, as it was covered by The New York Times. His breakout movie role was in "Fast Times at Ridgemont High" (1982), and he quickly won a reputation as one of the bad boys of Hollywood. Marriage to Madonna in the 1990s brought him further notoriety. Before the camera, he gained increasing renown, winning two Best Actor Academy Awards, for "Mystic River" in 2003 and "Milk" in 2008. Behind the camera, he has directed such movies as "The Crossing Guard" (1995) and "Into the Wild" (2007). A longtime political activist, Penn has roiled conservative waters with visits to Cuba, pre-invasion Iraq and Venezuela. More recently, he co-founded a humanitarian organization to help the people of Haiti after the 2010 earthquake there.