The 17 'Known' Girlfriends of Hugh Hefner (in Order of Hotness)

Hugh Hefner, the man who inspired thousands of women across the country to get Playboy bunny tramp stamps, has announced that he’s ready to settle down with his one true love, Crystal Harris. In honor of his commitment to Crystal (and his obvious commitment to Viagra), we’ve rounded up the hottest pictures of all his known girlfriends. And while we’re sure Hugh’s had many more girlfriends in his 84 years, we’re absolutely convinced that these 17 are the sexiest.

#17. Tina Marie Jordan

Tina Marie was a loan processor trying to get her real estate license when she met Hefner. Marie was Playmate of the month for March 2002. Tina’s been a regular on the The Howard Stern Show since before she become a playmate and she has continued to make appearances.

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#16 Carrie Leigh

Carrie Leigh, known as “Baby Boo-Boo” to Hef’s “Daddy,” Leigh was a playboy cover model in 1983 and 1986. Leigh now runs a website and a magazine called Nude.

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#15 Bridget Marquardt

Bridget Marquardt appeared on the famous reality show Girls Next Door… although most scenes are of her talking to her Cat, Gizmo. Marquardt had a show on the Travel Chanel in 2009 called Bridget’s Sexiest Beaches, but it ended after the first season.

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#14 Karen Christy

Karen Christy, a platinum blonde Bunny-in-training from Texas met Hugh when he was traveling through Chicago. Hef calls this relationship “his most passionate one –while it lasted.” Staffers made sure that Karen visited Mansion West only when Barbi (Hugh’s girlfriend) was on the road. The scheme worked, at least until Time magazine published photos of Hef and Karen together.

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#13 Marilyn Cole

Marilyn Cole was Playboy’s January 1972 Playmate of the Month as well as 1973’s Playmate of the Year. That makes her the the only Briton to hold that title. She started off as a bunny at the Playboy Club in London and was pursued romantically by both Hef and Victor Lownes, who at the time was president of Playboy Enterprises. She is currently married to Victor.

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#12 Sondra Theodore

Sondra Theodore. a former Sunday school teacher was playboy magazine’s Playmate of the month for its July 1977 issue. She can be seen on the famous Playball pinball machine alongside Hefner and fellow Playmate Patti Mcquire.

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#11 Kendra Wilkinson

Kendra Wilkinson was the third girlfriend on the show The Girls Next Door. Wilkinson met Heffner at his birthday party in 2004 where she was hired to be one of the “painted girls” (women who are nude except for body paint). She currently stars in a spinoff of Girls Next Door, titled Kendra, which focuses on her life after leaving the Playboy Mansion and getting engaged to Colts player, Hank Baskett. Baskett and Wilkinson had a baby boy in December 2009.

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#10 Lillian Muller

Lillian Müller appeared as Playmate of the month in August 1975 and was named Playmate of the year in 1976. Müller appeared in Van Halen’s “Hot for Teacher” video as the chemistry teacher. She also played Rob Stewart’s love interest in his 1976 “Do Ya Think I’m Sexy?”

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#9 Shannon Tweed

Shannon Tweed is a Canadian actress and model. She’s one of the most successful actresses of mainstream erotica and is identified with the genre called Erotic Thriller. Tweed appeared in Playboy as Playmate of the month in November 1981 and Playmate of the year in 1982. She currently lives with her Gene Simmons of Kiss and their two children.

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#8 Isabella St. James

Isabella St.James, published the first and only book ever written by a Playboy girlfriend in 2006 called Bunny Tales: Behind Closed Doors at the Playboy Mansion. St. James was 26 and still in law school when she was picked up at a local bar to live in the mansion. St James says she had “less than 15 intimate minutes” with Hef in her two-and-a-half years at the Mansion.

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#7 Donna Michelle

Donna Michelle was Playmate of the Month in December 1963 and Playmate of the year in 1964. Donna studied Ballet for years and even performed with the ‘New York City Ballet’ while in college. She was just 17 years old when she posed nude for Playboy.

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#6 Holly Madison

Holly Madison is best known for appearing as Hugh number one girlfriend with Bridget Marqudt and Kendra Wilkinson on the reality show, The Girls Next Door. Before moving into the mansion, Madison worked at Hooters to pay for her college tuition. She was never a playmate. Instead she did nude pictorials with her Girls Next Star costars in 2005 and appeared again on the covers in 2006, 2008 and 2009. You may also recognize her from the eighth season of Dancing with the Stars.

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#5 Crystal Harris

Crystal Harris is a British-American model and singer who was the Playboy Playmate of the Month for December 2009. Harris also appears in E!’s The Girls Next Door with the twins Kristina Shannon and Karissa Shannon.

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#4 The Shannon Twins

Kristina and Karissa Shannon are American models and twin sisters. They replaced Holly, Bridget and Kendra of The Girls Next Door. The girls appeared as Misses July and August in the double “Summer Issue” of Playboy that incorporated July and August in a single edition. On January 14, 2010 Hugh Hefner revealed that the twins were moving out of the mansion to the local Playmate house with his blessing. They will continue to appear on The Girls Next Door.

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#3 Kimberley Conrad

Kimberley Conrad (Heffner) was chosen as Playboy’s Playmate of the Month in January, 1988 and became Playmate of the year 1989. She is most known for marrying Playboy founder Hugh Hefner in 1989, an event which sparked worldwide media attention. The Hefner’s had two sons together: Marston Glenn Hefner and Cooper Bradford Hefner. After nine years of marriage, Conrad and Hefner separated, but remained married. After an 11 year separation, Hefner filed for divorce.

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#2 Barbie Benton

Barbi Benton appeared on the Playboy cover several times, as well as in nude photo layouts in the March 1970, December 1973, and January 1975 issues as Barbi Klein. Barbi changed her name when Hef suggested a more showbiz-friendly one.It was Barbi who found Hef the Playboy mansion in California and dubbed it Playboy Mansion West — and it wasn’t long before he gave up his Chicago mansion for the new one.

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#1 Brande Roderick

Brande Roderick first appeared in Playboy in April 2000 as Playmate of the month. In 2001 she was Playmate of the Year. You may recognize her from Starsky and Hutch, Celebrity Apprentice, and the Nanny Diaries. Roderick is married to Glenn Cadrez, a formed NFL linebacker.