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  1. Sean Penn, Conan

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

    Fri., Mar. 20, 2015 12:38 PM PDT
  2. Sean Penn, Good Morning America

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

    Thu., Mar. 19, 2015 9:18 AM PDT
  3. Kanye West, Jimmy Kimmel Live

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

    Mon., Mar. 16, 2015 8:00 PM PDT
  4. Sean Penn, Jimmy Kimmel

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

    Fri., Mar. 13, 2015 5:51 AM PDT
  5. Robin Wright, Vanity Fair

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

    Tue., Mar. 10, 2015 4:50 AM PDT
  6. Sean Penn, Alejandro G. Inarritu

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

    Mon., Feb. 23, 2015 6:37 AM PST
  7. Birdman, Best Picture, Oscars

    5 Biggest Jaw-Droppers at the 2015 Oscars

    Mon., Feb. 23, 2015 5:00 AM PST
  8. Charlize Theron, Sean Penn

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

    Thu., Feb. 05, 2015 8:24 PM PST
  9. 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''

    Wed., Jan. 28, 2015 6:31 PM PST
  10. Sean Penn

    Sean Penn: I Don't Miss My Gun Collection

    Tue., Jan. 13, 2015 1:30 PM PST
  11. Sean Penn, Charlize Theron

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

    Sun., Jan. 11, 2015 12:52 AM PST
  12. Sean Penn, Charlize Theron

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

    Mon., Dec. 29, 2014 3:13 PM PST
  13. Dylan Penn, L'Officiel Italia

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

    Mon., Dec. 29, 2014 3:05 PM PST
  14. Justin Bieber

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

    Fri., Dec. 05, 2014 12:43 PM PST
  15. Charlize Theron, Sean Penn

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

    Fri., Nov. 21, 2014 1:53 PM PST
  16. Sean Penn, Madonna

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

    Mon., Nov. 10, 2014 6:13 AM PST
  17. Charlize Theron, Sean Penn

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

    Mon., Oct. 06, 2014 9:59 AM PDT
  18. Dylan Penn, Vanity Fair

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

    Thu., Sep. 18, 2014 3:21 PM PDT
  19. Charlize Theron, Ring

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

    Fri., Jul. 25, 2014 5:11 AM PDT
  20. Charlize Theron

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

    Mon., Jul. 07, 2014 10:08 AM PDT
  21. Charlize Theron Instagram

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

    Tue., Jun. 03, 2014 1:17 PM PDT
  22. Charlize Theron

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

    Wed., May. 28, 2014 3:00 PM PDT
  23. Charlize Theron, Sean Penn

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

    Tue., May. 20, 2014 10:46 AM PDT
  24. Charlize Theron, Vogue

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

    Mon., May. 19, 2014 9:13 AM PDT
  25. Jay Z, Beyonce

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

    Sun., May. 18, 2014 8:30 AM PDT