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

13. Holly Madison

Best known as the head girlfriend on the Playboy reality seriesThe Girls Next Door, Holly Madison had seniority over the other two main girlfriends. Madison began dating Hefner in 2001 while mansion-mates Kendra Wilkinson and Bridget Marquardt joined up with Hefner in 2003. She’s also an example of a girl associated with Hefner who was never officially a Playmate, just like the rest of the series’ cast.

Despite this fact, Madison went on to cover the magazine both during the series and after its conclusion in 2009. Originally a Hooters waitress, Madison still remains in show business and was seen on Season 8 of Dancing with the Stars. Madison also garnered her own two season reality series called Holly’s World.