Hef's Girls

1. Brande Roderick made waves in Hef's heart, and most recently on Donald Trump's Celebrity Apprentice.(Photo: Zuma Press)

2. Shannon Tweed cozied to Hef then became synonymous with the erotic thriller. (Photo: Everett Collection)

3. Barbi Benton, pictured with Vegas icon Robert Urich, dated Hef for six years then became a recording and B-Movie star. (Photo: ABC/Retna)

4. Kimberly Conrad Hefner achieved heights rarely seen by the average Playmate--she married then divorced Hef, and gave birth to his two sons. (Photo: Getty Images)

5. Izabella St. James fogged Hef's windows then wrote a steamy tell-all about being a Bunny. (Photo: CelebrityPhoto.com)

6. Tina Jordan was a playmate, Hef Gal and former Surreal Life cast members. She occasionally guests on Howard Stern's radio show. (Photo: FilmMagic)

7. Crystal Harris is currently counted as one of Hef's current girlfriends, along with twins Karissa and Kristina Shannon.(Photo: WireImage)

8. Lillian Muller taught Hef a thing or two, having been his lady friend and the chemistry expert in Van Halen's "Hot for Teacher" video. (Photo: Splash News)

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9. Brande Roderick heated up Hef's heart, and ours! (Photo: Zuma Press)

10. Kristina Shannon and Karissa Shannon hold the current title of Hef's Beloved(s), but these bad girls have previous busts for marijuana.(Photo: Rex USA)