Sean Penn has been linked to some super famous ladies over the years, including Madonna, but the actor draws even more attention for his age-gap romances.

Sean Penn and his model girlfriend, Valeria Nicov, are back stateside following a romantic trip to Spain. The couple was ...

The pop superstar and the future Oscar-winning actor married in 1985, just six months after they first met on the set of her ...

Sean Penn raised ire when he compared the L.A. fires to the situation in the Middle East. Penn was a guest on Anderson Cooper 360, where he described what he had been seeing as a resident living ...

Sean Penn's 'Immersive' Ukraine War Documentary Previewed in New Trailer Sean Penn and Girlfriend Olga Korotyayeva Spend Date Night at Giorgio Baldi in Los Angeles Sean Penn and Girlfriend Olga ...

Sean Penn compared the devastation in Los Angeles caused by ongoing fires to damage in the Middle East, in an interview with CNN's Anderson Cooper Monday evening. 'This is kind of been a worst ...

Madonna, now 66, and Penn, now 64, began dating in February 1985 after meeting ... so you couldn’t hear anything. It got Sean riled up,” adds her brother Christopher Ciccone, who is also ...

“Sean Penn was pretty pissed off and I guess wrote ... Never miss a story — sign up for PEOPLE's free daily newsletter to stay up-to-date on the best of what PEOPLE has to offer , from ...