(147 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. Kendra Wilkinson-Baskett

    Kendra Wilkinson-Baskett Swears She Was ''Never Friends'' With Holly Madison: ''We Just F--ked the Same Man''

  4. Cooper Hefner, Scarlett Byrne

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

  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. Holly Madison, Instagram

    Holly Madison Responds to Kendra Wilkinson-Baskett, Explains How She'll Tell Daughter About Her Playboy Past—Watch Now!

  8. Holly Madison, Hugh Hefner

    Holly Madison Responds to Hugh Hefner's Claims She's ''Rewriting History'': ''He Can't Grasp the Fact a Woman Would Have a Message''

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

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

  10. 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?

  11. 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"

  12. Holly Madison

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

  13. Holly Madison, Hugh Hefner

    Holly Madison Calls Hugh Hefner a ''Manipulator,'' Says He Offered Her Drugs and Shares Secrets About Their Sex Life

  14. Jennifer Lopez, Hair

    New Beauty Etiquette: Why Last Week’s Must-Dos Are Suddenly Not Cool

  15. Holly Madison, Instagram

    Holly Madison Reveals She Contemplated Suicide While Living at the Playboy Mansion in New Memoir

  16. Kendra Baskett, Hugh Hefner

    Did Hugh Hefner Just Save Kendra Wilkinson's Marriage?! Playboy Founder Tells Her He Thinks Hank Baskett Was Set Up

  17. Kendra Wilkinson

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

  18. Morgan Freeman, Drew Carey, Hugh Hefner

    Veterans Day: Salute Morgan Freeman, Drew Carey and More Celebs Who Served Our Country

  19. Kendra Wilkinson, Hugh Hefner, Alijah Mary Baskett

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

  20. Miss December Kennedy Summers

    Kennedy Summers Named Playboy's 2014 Playmate of the Year! Meet the Sexy Star

  21. Hugh Hefner, Crystal Hefner, Twitter

    Hugh Hefner Celebrates His 88th Birthday With Casablanca Night, Shares Party Pictures on Twitter

  22. Hugh Hefner, Margot Robbie

    Margot Robbie Wanted for Playboy: Hugh Hefner Thinks She'd Be Great!

  23. Crystal Hefner, Hugh Hefner, Twitter

    Crystal Hefner, Then and Now: Has Hugh Hefner's Wife Changed Over the Years?

  24. Hugh Hefner, Crystal Hefner, Charlie, Holiday Card, Twitter

    Hugh Hefner and Wife Crystal Pose in Their Pajamas in Cuddly Christmas Card—See the Pic!

  25. Morgan Freeman, Drew Carey, Hugh Hefner

    Celebrity Veterans: Drew Carey, Morgan Freeman & More Brave Stars Who Served in the Military

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