Penn, Sean

Penn, Sean

Sean Penn might be the best actor of his generation. Perhaps that's what Scarlett Johansson sees in him, as these two started dating in early 2011.
Rating: 5.0 / 5.0
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.
Rating: 3.0 / 5.0
Sean Penn Pic

Sean Penn Pic

Sean Penn is one of the greatest actors in the world. His political views have often overshadowed his talent, however.
Rating: 2.6 / 5.0
Sean Penn Picture

Sean Penn Picture

Sean Penn is an outspoken actor. He has fired back against critics that cynically think his focus on Haiti is purely image-based.
Rating: 2.6 / 5.0
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.
Rating: 2.2 / 5.0
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?!
Rating: Unrated
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.
Rating: Unrated
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.
Rating: Unrated
Sean Penn Photograph

Sean Penn Photograph

No one doubts the acting ability of Sean Penn. Some take issue with his political stances, however.
Rating: Unrated
Sean Penn Smoking

Sean Penn Smoking

Sean Penn is a renowned smoker. It's done a lot of things for his looks too.
Rating: Unrated
Keep it Classy Sean

Keep it Classy Sean

Sean Penn sure knows how to dress to impress. This is him on the red carpet mind you.
Rating: Unrated
Sean Penn Mustache

Sean Penn Mustache

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