10 Things You Did Not Know about Sean Penn

6. His Rocky Relationship with “The Material Girl”

Penn’s 1985 marriage to pop superstar Madonna gained him lots of media attention. The two starred in the much-derided 1996 film, Shanghai Surprise. Madonna went on to call Penn “the coolest guy in the universe” in the liner notes of her album True Blue, which was dedicated to her actor husband. Their tumultuous relationship was marred by violent outbursts against the press. He even served time in jail for striking a film-extra. Penn also admitted to hitting Madonna over the head with a baseball bat, but she did not press charges. In 1988, Penn was charged with felony domestic assault, for allegedly beating his wife for hours. Madonna later dropped the charges, but filed for divorce a week later. It was finalized in 1989.