Madonna and Sean Penn at Charity Auction

Madonna and Sean Penn at Charity Auction

Madonna and Sean Penn team up for a charity gala for the African nation of Malawi at Art Basel in Miami on December 2nd, 2016. Are they getting back together?!
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Madonna and Sean Penn Wedding Pic

Madonna and Sean Penn Wedding Pic

Madonna and Sean Penn share a never-before-seen wedding photo from their ceremony back in 1985. They just now released the photo to sell at a charity auction.
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Madonna and Sean Penn Wedding Photo

Madonna and Sean Penn Wedding Photo

Madonna and Sean Penn share a never-before-seen wedding photo from their ceremony back in 1985. They just now released the photo to sell at a charity auction.
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Sean Penn: The Last Face Press Conference In Cannes, France

Sean Penn: The Last Face Press Conference In Cannes, France

Sean Penn attends the 'The Last Face' Press Conference during the 69th annual Cannes Film Festival at the Palais des Festivals on May 20, 2016 in Cannes, France.
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Madonna and Sean Penn throwback pic

Madonna and Sean Penn throwback pic

Madonna posted this throwback photo of her and Sean Penn in August 2015.
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Sean Penn, Charlize Theron Red Carpet Pic

Sean Penn, Charlize Theron Red Carpet Pic

Sean Penn and Charlize Theron in happier times. The couple broke up after 18 months of dating.
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Sean Penn and Charlize Theron

Sean Penn and Charlize Theron

Sean Penn and Charlize Theron broke up unexpectedly last week. Now, sources are saying Theron cut Penn loose in particularly brutal fashion.
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Sean Penn Smoking

Sean Penn Smoking

Sean Penn is a renowned smoker. It's done a lot of things for his looks too.
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Charlize Theron and Sean Penn

Charlize Theron and Sean Penn

Charlize Theron and Sean Penn don't make many public appearances. But here they are at the 2014 MET Gala.
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Sean Penn Image

Sean Penn Image

Sean at a charity event. This guy always looks like he wants to to punch somebody.
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Sean Penn, Esquire

Sean Penn, Esquire

Sean Penn on the cover of Esquire. Interesting guy.
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Sean Penn Mustache

Sean Penn Mustache

Sean Penn and that mustache ... wow. Quite the look. Up or down, whaddaya think?
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