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(44 Results)
  1. Playboy Then and Now Covers, Kimberley Conrad, Kimberley Hefner

    Playmates Then and Now: Playboy Models Recreate Their Iconic Covers Decades Later

  2. Jaylene Cook, Playboy

    Playboy Model Sparks Outrage Over Nude Photo Atop Sacred Mountain

  3. Armie Hammer, The Late Late Show

    Armie Hammer Had a Middle School Business Selling Playboy and Lotion

  4. Kendra Wilkinson-Baskett, Hugh Hefner

    Kendra Wilkinson-Baskett Shares Heartfelt Tribute to Hugh Hefner on His 91st Birthday: ''I'll Celebrate You Forever!''

  5. Hugh Hefner

    Hugh Hefner Meets the Actor Who's Playing Him in His New Docu-Series

  6. Cooper Hefner, Hugh Hefner

    Hugh Hefner's Son Shares an Update on His Dad's Health and Putting Nudity Back in Playboy

  7. Vanna White

    Vanna White Reveals Playboy Regrets and Wheel of Fortune Dress Secrets

  8. Kendra Wilkinson

    Kendra Wilkinson-Baskett Says She’s ''Moved On'' From the Playboy World: I Don't Give a F--k About Impressing People

  9. Scarlett Byrne

    Harry Potter Actress Scarlett Byrne Strips Naked for Playboy

  10. History of Sexuality, Rihanna, Kate Upton, Emily Ratajkowski, Kim Kardashian, Playboy

    Posing for the Sports Illustrated Swimsuit Issue or Playboy Is Empowering to Whomever Feels Empowered--& to Each Her Own

  11. Scarlett Johansson, Playboy

    Scarlett Johansson Thinks Monogamy Is Unnatural

  12. Playboy

    Playboy Is Bringing Naked Pictorials Back: ''Nudity Was Never the Problem Because Nudity Isn't a Problem''

  13. Kendra Wilkinson-Baskett, Hugh Hefner

    Kendra Wilkinson-Baskett "Freaked Out" Over Hugh Hefner Death Hoax

  14. Kendra Wilkinson-Baskett, Bridget Marquardt

    Kendra Wilkinson-Baskett Would Give Bridget Marquardt the Most Precious Gift If She Were Her Secret Celebrity Santa

  15. Matthew McConaughey

    8 Bonkers Quotes From Matthew McConaughey's Playboy Interview

  16. Billy Bob Thornton, Playboy

    Billy Bob Thornton Says He'd Love to Make a Movie With Angelina Jolie's Ex Brad Pitt

  17. Bella Thorne, Playboy

    Disney's Bella Thorne Makes Her Playboy Debut

  18. Holly Madison

    Holly Madison Gives Birth to Baby No. 2

  19. Pamela Anderson, Playboy

    Was a Non-Nude Future What Playboy Needed? Here Are the Magazine's Current Stats

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