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  1. Charlize Theron, Sean Penn, HHH Gala

    Sean Penn Tells Piers Morgan That Charlize Theron Is "a Keeper"

    Wed., Jan. 22, 2014 1:19 PM PST
  2. Madonna, Instagram

    Sean Penn Talks Madonna in Haiti

    Tue., Jan. 14, 2014 2:34 PM PST
  3. Steven R. McQueen, Dylan Penn

    Dylan Penn and Steven McQueen Cozy Up at Help Haiti Home Gala

    Sun., Jan. 12, 2014 3:47 PM PST
  4. Charlize Theron, Sean Penn, HHH Gala

    Charlize Theron Convinces New Boyfriend Sean Penn to Get Rid of His Guns, Anderson Cooper Buys Sculpture of Weapons for $1.4 Million

    Sun., Jan. 12, 2014 9:10 AM PST
  5. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn Kiss and Cuddle at Help Haiti Home Benefit

    Sat., Jan. 11, 2014 8:50 PM PST
  6. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn's Date Night at the Movies—All the Details!

    Mon., Jan. 06, 2014 12:33 PM PST
  7. Charlize Theron

    Charlize Theron and Sean Penn Grab Coffee Together in Malibu--See the Pics!

    Sun., Jan. 05, 2014 5:30 PM PST
  8. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn Spend Holidays in Hawaii, Head Back to L.A. Together—See the Pics!

    Thu., Jan. 02, 2014 12:32 PM PST
  9. The Secret Life of Walter Mitty

    The Secret Life of Walter Mitty: 5 Things to Know About Ben Stiller's Latest Flick

    Wed., Dec. 25, 2013 1:45 PM PST
  10. Dylan Penn

    Dylan Penn Signs New Ad Campaign

    Tue., Dec. 17, 2013 5:38 PM PST
  11. Madonna, Sean Penn, SecretProjectRevolution, Gagosian Gallery

    Madonna Joins Ex Sean Penn in Haiti to Help Shine Spotlight on Earthquake Relief

    Tue., Nov. 26, 2013 6:06 AM PST
  12. Paul McCartney

    Paul McCartney's "Queenie Eye" Music Video Starring Johnny Depp & Kate Moss Debuts—Watch Now!

    Thu., Oct. 24, 2013 8:01 AM PDT
  13. Tom Hanks, Sean Penn, Arnold Schwarzenegger

    Tom Hanks Talks Trick-or-Treating With Sean Penn and Arnold Schwarzengger (Seriously!)

    Mon., Oct. 21, 2013 2:02 PM PDT
  14. Robert Pattinson, Dylan Penn

    Robert Pattinson Parties With Dylan Penn, Spurs Dating Rumors: See the Pic!

    Fri., Sep. 27, 2013 4:41 PM PDT
  15. Sean Penn, Madonna

    Madonna and Sean Penn Reunite, Party With Lindsay Lohan—See the Pics

    Wed., Sep. 25, 2013 9:45 AM PDT
  16. Sean Penn, Hopper Penn

    Sean Penn's Son Accused of Shoving Photographer During Argument

    Tue., Mar. 26, 2013 3:26 PM PDT
  17. Sean Penn, Cannes Film Festival

    Sean Penn's Haiti Relief Organization Receives $8.75 Million Grant

    Wed., Mar. 13, 2013 6:15 AM PDT
  18. Sean Penn, Hugo Chavez

    Sean Penn Mourns Death of Venezuelan President Hugo Chávez

    Tue., Mar. 05, 2013 8:30 PM PST
  19. Steven Spielberg

    Steven Spielberg to Lead 2013 Cannes Film Festival Jury

    Thu., Feb. 28, 2013 8:53 AM PST
  20. Inside The Actors Studio, Bradley Cooper

    Bradley Cooper Asked Sean Penn a Question During an Episode of Inside the Actor's Studio in 1999

    Fri., Feb. 08, 2013 2:35 PM PST
  21. Daniel Day-Lewis, Lincoln

    Lincoln's New Odds, Sacha Baron Cohen's Brain and Other Golden Globes Mysteries Answered

    Mon., Jan. 14, 2013 2:15 PM PST
  22. Anderson Cooper

    Anderson Cooper Drops F-Bombs, Scared Sean Penn Would Beat Him Up

    Sun., Jan. 13, 2013 10:38 AM PST
  23. Emma Stone, Ryan Gosling, Gangster Squad

    Gangster Squad: 5 Things to Know About the Crime Drama Starring Ryan Gosling and Emma Stone

    Fri., Jan. 11, 2013 12:30 PM PST
  24. Emma Stone, Ryan Gosling, Gangster Squad

    Ryan Gosling: Emma Stone Owes Me Money!

    Tue., Jan. 08, 2013 11:53 AM PST
  25. Josh Brolin, Sean Penn

    Josh Brolin Hits Gangster Squad Premiere Solo Following Bust for Public Intoxication

    Mon., Jan. 07, 2013 10:00 PM PST