Top 15 Hottest Women Hugh Hefner Has Been With

Is there a person alive unfamiliar with the Playboy brand? Whether it’s the iconic bunny head, the girls or the magazine itself, Playboy has stayed iconic throughout the years. The publication recently made headlines by halting nude photography, but they vow to keep the content scintillating in other ways.

But what is more iconic about Playboy than the man, the myth, the legend himself: Hugh Hefner. The now 89-year-old is effectively worth almost $50 million and is entirely self-made. Other than his obvious business prowess, the owner of Playboy Enterprises is known for being just that: a playboy. Between multiple marriages and girlfriends throughout time, as well as living in the women-filled Playboy mansion, Hefner is something of a ladies man. In fact, he’s pretty much the ladies' man to end all ladies' men – but who can blame him? All of his partners, no matter how serious, are all at the very least seriously gorgeous. These 15 are what could be considered the cream of his crop.

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15 Carrie Leigh

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If you go through Playboy covers during the early to mid-80s, Carrie Leigh will show up quite a bit. She was known infamously as a cover model for the magazine, but also as a known lover of Hefner, though he never considered her a girlfriend, nor did they ever get married. Instead, Leigh was used as eye candy more than anything, with Hef referring to her as his “Baby Boo-Boo.”

The role of girlfriend was never officially given to Leigh, but she saw their relationship as something substantial regardless of their official title, which led to being part of a “palimony” suit after the “breakup.” She now runs a magazine of her own – Nude.

14 Donna Michelle

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Donna Michelle posed nude for Playboy, becoming Playmate of the Month in December 1963 and was Playmate of the Year in 1964. These images were controversial at the time, and would be especially so today – Michelle was only 17 at the time of her nude modeling.

Michelle went on to study ballet, appearing in the New York City Ballet during college, but ultimately went on to try her hand in acting. She married at 17 and divorced husband David M. Ronne a little over four years later. Michelle was also an avid photographer and died at the age of 58, in 2004.

13 Holly Madison

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Best known as the head girlfriend on the Playboy reality series The Girls Next DoorHolly 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.

12 Sondra Theodore

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If you ever had a naughty thought about your teacher, then you aren’t alone. If you ever thought a naughty thought about your Sunday school teacher, however, you might need to repent. Hefner, however, isn’t so pious – Sondra Theodore was once a Sunday school teacher herself, but became Playmate of the Month for July 1977.

If you were around for this era, you might also remember the famed Playboy pinball machines. If you ever saw one, either in a picture or with your own two eyes, Theodore was featured as a model for the machine as well as Patti McGuire.

11 Tina Marie Jordan

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This model was labeled Playmate of the Month during March 2002. Despite her fame now for posing nude, Tina Marie Jordan originally met Hefner while trying to obtain her real estate license. After becoming romantically involved with him, she was enlisted to receive the coveted centerfold spot in the magazine.

After appearing in the magazine, Jordan has gone on to appear on The Howard Stern Show, hosts her own radio show and was on Season 7 of the reality show The Surreal Life. She still remains beautiful and well-figured at 43 years old and with one child. She actually had her daughter prior to her centerfold appearance, making the accomplishment all the more impressive.

10 Shannon Tweed

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This Canadian model went from being a Playmate to one of the foremost names in erotic cinema. Shannon Tweed appeared as both the centerfold for November 1981 and the Playmate of the Year for 1982 during her run with the magazine.

Perhaps now she’s not as known for her work with Playboy as she is with her new family. Tweed is married to Gene Simmons, known as the front man of the rock band KISS, and her role on the family’s reality show Gene Simmons Family Jewels. She’s been featured in many erotic thriller films and has also appeared on multiple television series throughout her career.

9 Bridget Marquardt


While never an official Playmate, Bridget Marquardt was one of Hefner’s girlfriends from 2003 to 2008. Her fame, instead of originating from being a magazine model, sprung from her time on the reality TV series focusing on the Playboy mansion, The Girls Next Door with other Hefner honeys like Holly Madison.

After appearing on the show, Marquardt did snag several nude pictorials for the magazine. From there, she has appeared in numerous movies and television shows. She departed from the Playboy brand in 2009. Her other novelty nuance was being very attached to her animals – namely Gizmo, a Persian cat that regularly appeared with her on Girls Next Door, though the animal passed in mid-2015.

8 Karen Christy

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Something has to be said about the girl that gave Hefner his most passionate relationship – and those are his own words. Karen Christy met Hefner in Chicago, though hailing from Texas, and from there the two started having an affair of sorts. It’s reported that Hefner’s staff would invite Christy to the Playboy mansion only when his current girlfriend, Barbi Benton, was out of town or on the road.

It might not sound like much of a scandal for Hef to be a philanderer, but the pictures of the duo together were big enough to make it into Time magazine who busted the two lovebirds.

7 The Shannon Twins

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While technically two girls, Kristina and Karissa Shannon are identical twin models. The two became publicly famous when they replaced the original three girlfriends on The Girls Next Door. When Playboy released a double edition, called the “Summer Issue” in July and August of 2009, the two girls appeared as the Playmates of the month for both months.

After leaving the mansion in 2010, Karissa went on to garner attention both by being involved in sex tapes with fellow celebs Spencer Pratt and Heidi Montag, as well as her own sex tape being released by Vivid Entertainment. She appeared in said tape with boyfriend Sam Jones III. The twins both appeared on Season 9 of Celebrity Big Brother in the UK.

6 Izabella St. James

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Izabella St. James never snagged the title of girlfriend or wife, but she did achieve one historic Playboy goal – she became the first to ever write a book, entitled Bunny Tales: Behind Closed Doors. In her tell-all, St. James revealed that of her entire stay at the Mansion, spanning about two-and-a-half years, she spent about 15 minutes total with Hef in an intimate setting.

St. James herself exceeds the known stereotype for Playmates as a former resident of Communist-occupied Poland that fled with her family at the age of 10. She holds a law degree and has since returned to her home country to star on the Polish version of The Real Housewives franchise.

5 Kendra Wilkinson

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Perhaps one of the most famous and still relevant Playmates, Kendra Wilkinson is still a star of reality TV and pop culture today. She first met Hefner in 2004 at his birthday party. She appeared to be a painted nude model, but Hefner saw potential in her enough to both make her one of his girlfriends and put her on the hit reality series The Girls Next Door.

After the conclusion of the show, Wilkinson maintained relevance by establishing her own brand on television. She has since married Hank Baskett, wide receiver for the football team the Philadelphia Eagles and stars in her show Kendra On Top.

4 Crystal Harris

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Crystal Harris first gained notoriety as one of the girls added to the last season of The Girls Next Door along with the Shannon Twins in an attempt to boost ratings. Unlike other former co-stars, Harris was a Playmate, snagging the coveted Playmate of the Month title during the December 2009 publication.

Perhaps the most notable accomplishment of Crystal Harris is getting Hefner to settle down – Hugh has been said to have given up other women in exchange for being married to Harris, whom he refers to as “the love of his life.” In case you’re curious, the two married when Hefner was 85 and Harris was 26 and are still currently married.

3 Barbi Benton

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Barbi Benton began her Playboy career when she was 18 as co-host of the entertainment show Playboy After Dark alongside Hugh Hefner. He asked her for a date while currently 42, but this didn’t deter Benton. They were together for several years during the Playboy hay days, meaning she was very prominent in the company during her time with Hefner.

She went on to cover the magazine four times: July 1969, March 1970, May 1972, December 1985, but never achieved a Playmate of the Month title. Other accomplishments include television appearances, work as a country singer, and movie appearances as both a guest and an actress.

2 Brande Roderick

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2000 was the year of Brande Roderick – she began her successful career as a Baywatch actress and became Playmate of the Month for April 2000, subsequently becoming Playmate of the Year in 2001. From there, Roderick went on to star in other films, including Out of Control (a Bollywood film), Starsky & Hutch, and The Nanny Diaries.

She also had parts on TV including some reality television shows such as Fear Factor, Gameshow Marathon, and the 2nd and 6th Seasons of The Celebrity Apprentice. During her Season 2 run, Roderick made it to the final four but was eliminated.

1 Kimberly Conrad

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The classic beauty Kimberly Conrad graced the centerfold for Playboy in January 1988 as that month’s Playmate of the Month, eventually becoming Playmate of the Year for 1989. That same year, Conrad married Hefner and became officially famous as the union gained massive media attention.

Just like their marriage was a media spectacle, their subsequent separation and divorce was also notable. The two remained married for nine years, separated and only got divorced 11 years later. The marriage produced two sons: Marston Glenn Hefner and Cooper Bradford Hefner. The two were actually what kept the two together after Conrad stated she didn’t want to put her children through a divorce.

Sources: Playboy, NY Daily News

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