(45 Results)
  1. Sean Penn, Leila George

    Sean Penn and New Girlfriend Leila George D'Onofrio Make Red Carpet Debut

  2. Sean Penn, Leila George

    Sean Penn Is Dating Vincent D'Onofrio's 24-Year-Old Daughter Leila: Get the Details on Their New Relationship

  3. Sean Penn, Stephen Colbert

    Sean Penn Hesitantly Signs Up for Twitter Thanks to Stephen Colbert

  4.  Hopper Penn, Sean Penn

    Sean Penn Almost Named His Son ''Steak'' Because He Loves Meat That Much (Yes, Seriously)

  5. Sean Penn, Charlize Theron, Cannes 2016

    Sean Penn, Charlize Theron and More Actor Exes Who Worked Together After Breaking Up

  6. Charlize Theron, Javier Bardem, Adele Exarchopoulos, Sean Penn

    Charlize Theron and Sean Penn Keep Their Distance in Cannes as Their New Movie Gets Panned

  7. Lee Daniels, Sean Penn

    Sean Penn Drops $10 Million Defamation Lawsuit Against Empire Co-Creator Lee Daniels

  8. Charlize Theron, WSJ Magazine

    Charlize Theron Talks Sean Penn Split: I Wasn't ''Ghosting'' Him

  9. Kate del Castillo, Veronica del Castillo

    Verónica del Castillo Talks About Her Relationship With Sister Kate Since El Chapo Controversy With Sean Penn

  10. Madonna, Sean Penn, SecretProjectRevolution, Gagosian Gallery

    Madonna Defends Sean Penn, States He Never Physically Assaulted Her During Their Rocky Marriage

  11. Dylan Frances Penn, Hopper Penn

    Sean Penn's Kids, Dylan Penn and Hopper Penn, Star in Their First Fashion Campaign Together

  12. Sean Penn, 60 Minutes

    Sean Penn Fires Back at Critics of His El Chapo Interview, Explains Why Article ''Failed" on 60 Minutes

  13. El Chapo, Charlie Rose, Sean Penn

    Sean Penn Has a "Terrible Regret" About His Conversation With El Chapo, but It's Not What You Think

  14. Sean Penn

    Sean Penn Isn't Worried About El Chapo Interview: "I've Got Nothin' to Hide"

  15. Sean Penn

    Sean Penn's Secret Meetings With "El Chapo" Revealed: 5 Biggest Revelations From the Interview

  16. Madonna, Sean Penn

    Madonna and Sean Penn Reignite Romance Rumors at Oscar Winner's Annual Haiti Benefit Gala

  17. Jimmy Kimmel Live, Mean Tweets

    Sean Penn and Liv Tyler Read "Mean Tweets" on Tonight's Jimmy Kimmel Live! (and Only One of Them Laughs)

  18. Khloe Kardashian, Lamar Odom

    Khloe Kardashian & Lamar Odom Call Off Divorce: 7 Celebrity Couples Who Have Done the Same

  19. Sean Penn, Jewel

    Jewel Reveals She Dated & Fell in Love With Sean Penn During His Split From Robin Wright

  20. Sean Penn, Dylan Penn, Madonna

    Sean Penn Introduces Daughter Dylan Penn to Madonna For the First Time After NYC Concert

  21. 1pm, Charlize Theron, Sean Penn

    Exes Charlize Theron & Sean Penn Reunite for South African Re-Shoots—See the Pics

  22. Minka Kelly, Sean Penn

    Is Minka Kelly Really Dating Sean Penn? Actress Breaks Silence on the Rumors!

  23. Charlize Theron, First Time Photographed Post-Breakup, EXCLUSIVE

    Charlize Theron Photographed for the First Time Since Her June Breakup With Sean Penn: See the Exclusive Photos!

  24. Sean Penn

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

  25. Sean Penn, Charlize Theron

    Sean Penn and Charlize Theron Break Up