Sean Penn Gareth Cattermole/Getty Images Sean Penn is no stranger to drama, both on and off the screen. In addition to his career as an Oscar-winning actor and his relationships with A-listers including Madonna, Robin Wright and Charlize Theron, Penn has made headlines through the years for controversial behavior and comments. Keep scrolling to for a look back at Penn's biggest controversies over the years: Vinnie Zuffante/Michael Ochs Archives/Getty Images Alleged Abuse of Madonna Penn was married to the "Queen of Pop" from 1985 to 1989.