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  1. Kanye West, Jimmy Kimmel Live

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

  2. Sean Penn, Jimmy Kimmel

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

  3. Robin Wright, Vanity Fair

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

  4. Sean Penn, Alejandro G. Inarritu

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

  5. Birdman, Best Picture, Oscars

    5 Biggest Jaw-Droppers at the 2015 Oscars

  6. Charlize Theron, Sean Penn

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

  7. 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''

  8. Sean Penn

    Sean Penn: I Don't Miss My Gun Collection

  9. Sean Penn, Charlize Theron

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

  10. Sean Penn, Charlize Theron

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

  11. Dylan Penn, L'Officiel Italia

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

  12. Justin Bieber

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

  13. Charlize Theron, Sean Penn

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

  14. Sean Penn, Madonna

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

  15. Charlize Theron, Sean Penn

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

  16. Dylan Penn, Vanity Fair

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

  17. Charlize Theron, Ring

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

  18. Charlize Theron

    Charlize Theron Looks Incredible in Gold Dior Mini Dress With Sean Penn at Paris Haute Couture Fashion Week

  19. Charlize Theron Instagram

    Charlize Theron Sings With Seth MacFarlane During Date Night With Sean Penn—Get the Details!

  20. Charlize Theron

    Charlize Theron Wears Her Boyfriend's Giant, Black Undershirt and Still Looks Perfect—See the Pic!

  21. Charlize Theron, Sean Penn

    Charlize Theron Reveals What Might Happen If She Ever Breaks Up With Sean Penn—Watch Now!

  22. Charlize Theron, Vogue

    Charlize Theron Covers Vogue, Opens Up About "Effortless" Relationship With Sean Penn

  23. Jay Z, Beyonce

    Beyoncé and Jay-Z Release "Run" Music Video Featuring Blake Lively, Sean Penn and More: Watch!

  24. Kanye West, Kim Kardashian, MET Gala

    Kim and Kanye, Blake Lively and Ryan Reynolds, Johnny Depp and Amber Heard: See These Couples and More on the 2014 Met Gala Red Carpet

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