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

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

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

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)

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

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

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

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)

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)