The long list of men Madonna has slept with – this will shock you! (With Pictures)

7.  Sean Penn

One of Madonna’s more notorious fellas is actor Sean Penn, to whom she was married from 1985 to 1989. Their relationship was often tumultuous, and always in the limelight. While their movie together,Shanghai Surprise, was not a box office hit, the relationship was (at least for a while). She wanted to divorce him in 1987, but they stuck it out, only to finally split ways for good in ’89. The pair never had children together, but he did have two kids eventually. Penn married again, to the talented and attractive,Robin Wright, but they too ended up divorcing. Third time’s a charm, Sean? These days, Penn not only acts, but he’s a cutthroat political activist. He’s also still charming the ladies and recently dated (then broke up with) the glamourous actress, Charlize Theron. While there are those that may not find Penn to be the typical handsome actor type, he still exudes the charisma and sex appeal that keeps the ladies wanting more. There are still those that hope he and Madonna will get back together, especially since he was even spotted at one of her concerts recently.