Sean Penn has been nominated for the Academy Award for Best Actor five times, winning it on two occasions. A chameleonic performer, he is famous for his participation in famous films including Carlito's Way, Dead Man Walking, The Thin Red Line, Mystic River, 21 Grams and Milk and for directing, producing and screenplaying Into the Wild.
In August 1985, Penn's personal life began to attract media attention following his first marriage to singer Madonna in Malibu. The two star together in Shanghai Surprise, and Madonna dedicates her third album to him, entitled True Blue, where she defines the Californian actor as the coolest guy in the universe. The relationship is also marked by violent backlash against the press, including an incident in which Penn was arrested for assaulting a photographer on a film set. For this episode, the actor was sentenced to 60 days in prison in mid-1987, serving 33. Penn was later also accused of domestic violence. In January 1989 the two signed divorce papers.
After 7 years of engagement, in 1996 he married the actress Robin Wright, with whom he had two children. At the end of 2007, the couple announced their separation. Penn and his wife briefly reconciled a couple of times, before announcing their final divorce in 2010.
In 2011 he had a five-month relationship with actress Scarlett Johansson. Between 2014 and 2015 he was romantically linked to actress Charlize Theron. In 2016 he became involved with Leila George, daughter of the actors Greta Scacchi and Vincent D'Onofrio, whom he then married on 30 July 2020. The couple divorced on 15 October 2021.