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  1. Sean Penn, Charlize Theron

    Charlize Theron and Sean Penn Walk Their First Red Carpet Together—See the Pic!

    Mon., Mar. 03, 2014 9:50 AM PST
  2. Charlize Theron, Sean Penn

    Charlize Theron Cozies Up to Sean Penn at Pharrell Williams' Pre-Oscar Party—See the Pics!

    Fri., Feb. 28, 2014 4:18 AM PST
  3. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn's Romantic Weekend in Mexico—All the Exclusive Details!

    Tue., Feb. 18, 2014 10:00 AM PST
  4. Charlize Theron, Sean Penn

    Charlize Theron and Sean Penn Step Out for Low-Key Date Night in Beverly Hills—See the Pics!

    Wed., Feb. 12, 2014 8:08 AM PST
  5. Robin Wright, Golden Globes

    Robin Wright Admits to Botox, Talks Getting Married Again After "Devastating" Divorce From Sean Penn

    Mon., Feb. 10, 2014 6:39 PM PST
  6. Charlize Theron, Sean Penn

    Sean Penn and Charlize Theron Makeout for the First Time in Public—See the Pics!

    Sat., Feb. 08, 2014 7:46 AM PST
  7. Sean Penn, Charlize Theron, Jackson

    Sean Penn Cuddles With Charlize Theron's Son Jackson as Couple Enjoys Romantic Stroll on the Beach

    Mon., Feb. 03, 2014 11:51 AM PST
  8. Charlize Theron, Sean Penn, HHH Gala

    Inside Charlize Theron and Sean Penn's Relationship—How the Couple Is Heating Up

    Tue., Jan. 28, 2014 12:07 PM PST
  9. Sean Penne, Charlize Theron

    Sean Penn and Charlize Theron Hold Hands on Romantic Getaway—See the Cute Couple's Rare PDA!

    Mon., Jan. 27, 2014 10:34 AM PST
  10. Sean Penn, Charlize Theron, Jackson

    Sean Penn Goes Grocery Shopping With Charlize Theron and Her Son Jackson—See the Pics!

    Thu., Jan. 23, 2014 7:58 AM PST
  11. 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
  12. Madonna, Instagram

    Sean Penn Talks Madonna in Haiti

    Tue., Jan. 14, 2014 2:34 PM PST
  13. 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
  14. 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
  15. 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
  16. 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
  17. Charlize Theron

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

    Sun., Jan. 05, 2014 5:30 PM PST
  18. 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
  19. 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
  20. Dylan Penn

    Dylan Penn Signs New Ad Campaign

    Tue., Dec. 17, 2013 5:38 PM PST
  21. 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
  22. 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
  23. 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
  24. Robert Pattinson, Dylan Penn

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

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

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

    Wed., Sep. 25, 2013 9:45 AM PDT