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  1. Sean Penn

    Sean Penn Spends Father's Day With Daughter Dylan in First Outing Since Charlize Theron Breakup

  2. Sean Penn, Charlize Theron

    Sean Penn and Charlize Theron Break Up

  3. Sean Penn, Home

    Sean Penn Lists His Private Malibu Estate for $6.5 Million—Take a Look Inside!

  4. Charlize Theron

    Charlize Theron Discusses ''Sacred'' Relationship With Sean Penn, Says Going Bald for Mad Max Was ''Freeing''

  5. Charlize Theron, Jackson Theron, Sean Penn

    Sean Penn & Charlize Theron's Son Jackson Share a Snow Cone—And It's the Cutest Thing You'll See All Day

  6. Charlize Theron, Esquire

    Charlize Theron Considers the ''Possibility'' of Marriage and Opens Up About Her ''Hot'' Love Sean Penn in Esquire

  7. Sean Penn, Conan

    Sean Penn Blames George W. Bush and Dick Cheney for Creating ISIS—Watch Now!

  8. Sean Penn, Good Morning America

    Sean Penn Dodges Charlize Theron Engagement Questions on Good Morning America—Watch Now

  9. Kanye West, Jimmy Kimmel Live

    Jimmy Kimmel Wants Kanye West to Read Mean Tweets: Will He Do It?

  10. Sean Penn, Jimmy Kimmel

    Sean Penn Is Team Kaitlyn for The Bachelorette, Plus He and Charlize Theron Are Fans of The Bachelor—Watch Now!

  11. Robin Wright, Vanity Fair

    Robin Wright Credits Sean Penn With Making Her a Better Lover for Fiancé Ben Foster: "I've Never Been Happier"

  12. Sean Penn, Alejandro G. Inarritu

    Birdman's Alejandro González Iñárritu Thought Sean Penn's Green Card Joke Was "Hilarious"

  13. Birdman, Best Picture, Oscars

    5 Biggest Jaw-Droppers at the 2015 Oscars

  14. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn Go House Hunting Together—See the Pic!

  15. Sean Penn, Charlize Theron

    Sean Penn Is ''Surprised to Be in Love'' at 54 and if He Marries Charlize Theron He'd Consider It "a First Marriage''

  16. Sean Penn

    Sean Penn: I Don't Miss My Gun Collection

  17. Sean Penn, Charlize Theron

    Charlize Theron, Bill Clinton Help Sean Penn Raise $6 Million for Haiti

  18. Sean Penn, Charlize Theron

    Charlize Theron and Sean Penn Are Talking Weddings: They're "Discussing When and Where"

  19. Dylan Penn, L'Officiel Italia

    Dylan Penn Nabs Her First Major Magazine Cover with L'Officiel Italia—Check It Out!

  20. Justin Bieber

    Justin Bieber Dyes Hair Platinum Blond, Sean Penn Goes Golden Too—See the Pics!

  21. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn ''So Cute'' During Date Night in Hollywood: All the Details!

  22. Sean Penn, Madonna

    Madonna's Wedding Dress From Sean Penn Marriage Sells for $81,250 at Charity Auction

  23. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn Spotted Filming The Last Face Together in South Africa—See the Pic!

  24. Dylan Penn, Vanity Fair

    Dylan Penn Talks Robert Pattinson, Justin Timberlake and Her Naked Photo Spread

  25. Charlize Theron, Ring

    Is Charlize Theron Engaged to Sean Penn? Star Spotted With Gleaming Ring on That Finger

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