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  1. Ines Rau, First Transgender Playboy

    Meet Ines Rau, Playboy's First Transgender Playmate

  2. Hugh Hefner, Playboy Cover

    Young Hugh Hefner Graces Playboy Cover in Honor of the Founder's Death

  3. Hugh Hefner

    Hugh Hefner's Final Years: Inside the Playboy Founder's Biggest Heartbreak

  4. Crystal Harris, Hugh Hefner

    Crystal Hefner Breaks Her Silence After Hugh Hefner Is Laid to Rest

  5. Hugh Hefner

    Hugh Hefner's Most Controversial Moments

  6. Hugh Hefner

    Examining Hugh Hefner's Style: How the Playboy Founder Made Pajama Dressing a Force in Fashion

  7. Hugh Hefner, The House Bunny

    Why We Loved Hugh Hefner: See His Best and Craziest Moments

  8. Hugh Hefner, Crystal Harris, Instagram

    Hugh Hefner Talks About "True Love" in His Final E! News Interview

  9. Kendra Wilkinson, Pamela Anderson, Crystal Harris, Hugh Hefner

    Looking Back at the Most Important Women in Hugh Hefner's Life

  10. Marilyn Monroe, Playboy Magazine

    Watch Hugh Hefner Reflect on Playboy's First Edition With Cover Star Marilyn Monroe in 2008 E! News Interview

  11. Hugh Hefner, The House Bunny

    Hugh Hefner's Movie and TV Cameos

  12. Hugh Hefner

    Determination, $8,000 and an Idea: The Story of How Hugh Hefner Started Playboy

  13. Pamela Anderson

    Lingerie-Clad Pamela Anderson Wipes Away Tears as She Mourns Hugh Hefner's Death

  14. Hugh Hefner

    Playboy's Most Iconic Magazine Covers From 1953 to 2016

  15. Hugh Hefner

    Hugh Hefner Dead at 91: Stars Remember the Playboy Founder and "Hollywood Legend"

  16. Hugh Hefner, Bridget Marquardt

    Girls Next Door Star Bridget Marquardt Reacts to Hugh Hefner's Death

  17. Jenny McCarthy, Hugh Hefner

    Jenny McCarthy, Paris Hilton and More Playboy Models React to Hugh Hefner's Death

  18. Cooper Hefner, Hugh Hefner

    Hugh Hefner's Son Cooper Pays Tribute to Playboy Founder After His Death

  19. Serena Williams, Vanity Fair, August 2017

    How Posing Nude Became the Ultimate Celebrity Power Move

  20. Playboy Then and Now Covers, Kimberley Conrad, Kimberley Hefner

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

  21. Jaylene Cook, Playboy

    Playboy Model Sparks Outrage Over Nude Photo Atop Sacred Mountain

  22. Armie Hammer, The Late Late Show

    Armie Hammer Had a Middle School Business Selling Playboy and Lotion

  23. Kendra Wilkinson-Baskett, Hugh Hefner

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

  24. Hugh Hefner

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

  25. Cooper Hefner, Hugh Hefner

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