The long list of hot women Hugh Hefner has slept with – #2 will shock you! (With Pictures)

5. Kendra Wilkinson

Perhaps one of the most famous and still relevant Playmates,Kendra Wilkinson is still a star of reality TV and pop culture today. She first met Hefner in 2004 at his birthday party. She appeared to be a painted nude model, but Hefner saw potential in her enough to both make her one of his girlfriends and put her on the hit reality series The Girls Next Door.

After the conclusion of the show, Wilkinson maintained relevance by establishing her own brand on television. She has since married Hank Baskett, wide receiver for the football team the Philadelphia Eagles and stars in her show Kendra On Top.