Sean Penn

Sean Penn became famous playing Jeff Spicoli in Fast Times at Ridgemont High in 1982, which was a problem because Spicoli was a joke and Penn was not. He spent the 1980s fighting the typecasting and the tabloids simultaneously. The tabloids usually won. By the time Dead Man Walking arrived in 1995, he'd rebuilt his credibility through sheer obstinance. Two Oscars followed: Mystic River in 2003, Milk in 2008. He's the actor nobody in Hollywood seems to like but everybody keeps hiring.

Penn's current moment might be his most interesting in twenty years. Paul Thomas Anderson's One Battle After Another (2025) earned him an Oscar nomination for Best Supporting Actor, with critics calling it his best work in years. He's also become one of the few American celebrities who've actually shown up in Ukraine, making four trips since Russia's invasion and producing the documentary Superpower. Ukraine's government gave him the Order of Merit. He says he's thrilled to be divorced from his third wife. That tracks.

While married to Madonna, Penn was arrested four times for assaulting various people, including photographers, a nightclub patron, and a film extra on the set of Colors. He pled no contest to two of those charges and paid a $50 fine on each. The marriage ended in 1989. His second marriage, to Robin Wright, lasted fourteen years and produced two kids before they stopped reconciling. His third marriage, to Leila George, lasted just over a year before she filed for divorce. Three marriages, three divorces. The $50 fine is somehow the least remarkable part of his personal history.