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.

15 Carrie Leigh


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.”

14 Donna Michelle


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.

13 Holly Madison


Best known as the head girlfriend on the Playboy reality series The Girls Next Door, Holly 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.

12 Sondra Theodore


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.

11 Tina Marie Jordan


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.

10 Shannon Tweed


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.

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.

8 Karen Christy


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.

7 The Shannon Twins


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.

6 Izabella St. James


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.

5 Kendra Wilkinson


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.

4 Crystal Harris


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.

3 Barbi Benton


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.

2 Brande Roderick


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.

1 Kimberly Conrad


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.


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Top 15 Hottest Women Hugh Hefner Has Been With