Madonna & Sean Penn (1987)

Madonna & Sean Penn head home (then 1 West Street) in Photo by: Ron Galella.

Sean Penn... Now who doesn't think he's cool?  In a crazy kinda way - of course!

Sean Penn - yes, to me, some men are very handsome smoking a cigarette, Sean being one of them

Blast From the Bast Couples: Madonna and Sean Penn got married in 1985 but were divorced by 1989. More here.

Katie Holmes and Chris Klein

Blast From the Bast Couples: Madonna and Sean Penn got married in 1985 but were divorced by

Sean Penn and Charlize Theron in the front row at the Christian Dior Autumn/Winter 2014-2015 Couture Show

Front Row at Dior Haute Couture

Chatter Busy: Sean Penn Dating

Nominated for an Oscar at 20 and engaged to bad boy actor Sean Penn, Downton Abbey star Elizabeth McGovern was destined for greatness.

Robin Wright And Sean Penn's Kids Look Exactly Like Them

Robin Wright And Sean Penn's Kids Look Exactly Like Them

Boyfriend and girlfriend, actors Sean Penn and Robin Wright at the premiere of their motion picture "State Of Grace".

Pin for Later: 2015 Was the Year of Celebrity Breakups — See All the Couples Who Split Charlize Theron and Sean Penn

Charlize Theron and Sean Penn

Pin for Later: 24 Celebrity Couples Who Have Split Up in 2015 Charlize Theron and Sean Penn

dylan penn approves of sean penn dating charlize theron 01 Dylan Penn strikes a pose at the Dsquared2 first USA boutique opening on Tuesday (October 28) in Los Angeles. The 23-year-old model opened up about her father…

dylan penn approves of sean penn dating charlize theron 01 Dylan Penn strikes a pose at the first USA boutique opening on Tuesday (October in Los Angeles. The model opened up about her father…

Sean Penn, Charlize Theron Have Movie Date in Hollywood: Picture - Us Weekly

Sean Penn, Charlize Theron Have Movie Date in Hollywood: Picture

The hair + the outfit Sean Penn, Charlize Theron Have Movie Date in Hollywood: Picture - Us Weekly

Charlize Theron and Sean Penn arrive at the movie premiere of "A Million Ways to Die in the West" - May 15, 2014.  Theron and Penn began dating in December 2013, announced their engagement in December 2014, and ended the relationship in June 2015.

Charlize Theron and Sean Penn arrive at the movie premiere of "A Million Ways to Die in the West" - May 15, 2014. Theron and Penn began dating in December 2013, announced their engagement in December 2014, and ended the relationship in June 2015.

Charlize Theron & Sean Penn: Movie Date at ArcLight! | Charlize Theron, Sean Penn Photos | Just Jared

Charlize Theron & Sean Penn: Movie Date at ArcLight!: Photo Charlize Theron and her rumored new boyfriend Sean Penn step out together after seeing a movie at the ArcLight Cinemas on Sunday evening (January in Hollywood.

Sean Penn, actor, writer-director.   photo by Richard Avedon

Sean Penn by Richard Avedon I like the way he has used black and white in the picture. Because he is making you look at the photo in a different way which make the view look at it in a different way. Effortless style white tshirt black and white

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