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Hef's Girls

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Jun. 9 2009, Updated 7:31 a.m. ET

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We're taking a look back at some of the lovely ladies Hugh Hefner has dated.

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

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Brande Roderick made waves in Hef's heart, and most recently on Donald

Trump's Celebrity Apprentice.(Photo: Zuma Press)

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

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

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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)

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Barbi Benton, pictured with Vegas icon Robert Urich, dated Hef for six years

then became a recording and B-Movie star. (Photo: ABC/Retna)

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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)

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Source: Splash News

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)

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

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Izabella St. James fogged Hef's windows then wrote a steamy tell-all about

being a Bunny. (Photo: CelebrityPhoto.com)

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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)

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Tina Jordan was a playmate, Hef Gal and former Surreal Life cast members.

She occasionally guests on Howard Stern's radio show. (Photo: FilmMagic)

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

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Crystal Harris is currently counted as one of Hef's current girlfriends,

along with twins Karissa and Kristina Shannon.(Photo: WireImage)

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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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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)

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

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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)

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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)

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