A deep dive into Sean Penn's star-studded romantic past

The Oscar winner turns 60 today

Stars Insider

17/08/20 | StarsInsider

CELEBRITY Relationships

Sean Penn's reputation in Hollywood is a mixture of high regard for his profound work in films like 'Milk' and 'Mystic River,' along with some reticence for his eccentrically grumpy off-screen persona. He's gone from strength to strength in acting, and gone from controversy to controversy in headlines, but there has been one constant among it all: his affinity for talented women.

Penn's private life has been more of a hot topic than many of his films in recent years, and there's good reason for it, what with his romantic journey among the likes of Susan Sarandon and Charlize Theron, leading to his most recent, and very quiet, wedding to Leila George, who is one year younger than his own daughter.

The actor has cultivated a wild, experimental nature over the years, and has proposed to four other women in his past! Click through this gallery to see all the women Penn has romanced, or has been rumored to romance, over the years.

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