(203 Results)
  1. Holly Madison, Hugh Hefner

    Holly Madison Talks Hugh Hefner Split and What Grossed Her Out: Watch the Oprah: Where Are They Now? Video

  2. iHeartRadio Summer Pool Party, Holly Madison

    Holly Madison Signs Second Book Deal for If I Only Had A Date—Get the Details!

  3. Cooper Hefner, Scarlett Byrne

    Hugh Hefner's Son, Cooper Hefner, Is Engaged to The Vampire Diaries' Scarlett Byrne

  4. Carmen Ortega, Playboy

    Hollywood Cycle's Carmen Ortega Strips Down for Playboy! See the Super-Sexy Pics

  5. Miss August, Playboy

    In Her Own Words: Playboy's Miss August, Dominique Jane Sharpe, Bares All—Meet the Unexpected ''Girl Next Door''

  6. Hugh Hefner, Cooper Hefner, Holly Madison

    Hugh Hefner's Son Cooper Slams Holly Madison: ''She Is Famous for Being a Gold Digger''

  7. Hugh Hefner, Holly Madison, Kendra Wilkinson, Bridget Marquardt

    Kendra Wilkinson-Baskett Defends Hugh Hefner and Calls Out Holly Madison: "We're Witnessing Some Revenge"

  8. iHeartRadio Summer Pool Party, Holly Madison

    Exclusive! Holly Madison's Tell-All Memoir to be a TV Movie: Who's Going to Play the Former Playboy Bunny?

  9. Caroline Tula Cossey, Playboy

    Caroline "Tula" Cossey, Former Transgender Playboy Model, Talks Caitlyn Jenner: "It Was a Bit of a Shock"

  10. Hugh Hefner, Holly Madison, Kendra Wilkinson, Bridget Marquardt

    Hugh Hefner Claims Holly Madison Has "Chosen to Rewrite History" With Her Memoir "to Stay in the Spotlight"

  11. Holly Madison

    Holly Madison's Surprising Advice to Aspiring Playboy Models: Don't Do It!

  12. Dani Mathers, Playboy, Playmate of the Year

    Playboy's 2015 Playmate of the Year Revealed: Meet Dani Mathers!

  13. Aubrey Plaza, Playboy

    Aubrey Plaza Jokes in Playboy That Chris Pratt "Forgot" Her Name After Guardians of the Galaxy Success

  14. Azealia Banks, Playboy

    Azealia Banks Poses Naked With Cats for Playboy, Reveals She Dated a 43-Year-Old Man When She Was 17

  15. Azealia Banks, Playboy

    Azealia Banks Poses Nude, Lands Cover of Playboy's Music Issue

  16. Brittany Ward, Playboy

    Kellan Lutz's Girlfriend Brittny Ward Is Playboy's Miss January 2015—See the Playmate's Pics!

  17. Kendra Wilkinson

    Kendra Wilkinson-Baskett "Didn't Know That Sex Was Involved" With Being Hugh Hefner's Girlfriend—Watch Now!

  18. Niecy Nash

    Niecy Nash Says Oral Sex Saves Marriages: "A BJ a Day Keeps the Divorce Attorney Away''

  19. Kendra Wilkinson, Hugh Hefner, Alijah Mary Baskett

    Kendra Wilkinson-Baskett Introduces Baby Alijah to Hugh Hefner at the Playboy Mansion—Watch Now!

  20. Lindsay Lohan

    Lindsay Lohan Snaps a Topless Photo in Dressing Room, Is Overshadowed by Completely Nude Portrait Behind Her

  21. Richard Lugner, Cathy Schmitz

    Billionaire Richard Lugner, 81, Marries 24-Year-Old Playboy Model Cathy Schmitz

  22. James Spader

    James Spader Reveals His Childhood Sexual Fantasy (and What He Regrets Most About It)

  23. Sherlyn Chopra, Playboy

    Sherlyn Chopra Is Playboy's First Indian Model Ever—See Her Sexy Shoot!

  24. Justin Theroux, Liv Tyler

    Liv Tyler Calls Justin Theroux's "Large Bulge" Distracting, Talks About Getting Nude for Playboy

  25. Kate Upton, Instagram

    Kate Upton on Posing for Playboy: "I Never Like to Say Never"

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