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The 15 Hottest Women Hugh Hefner Hooked Up With

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The 15 Hottest Women Hugh Hefner Hooked Up With

The world lost an icon late Wednesday night when Playboy founder (and it’s former Editor) Hugh Hefner passed away at the Playboy Mansion while surrounded by loved ones. He was 91 years old and one could argue that he lived a full life.

He personified what Playboy was all about from its inception in 1953 through present day. Playboy was one of the main forces behind the sexual liberation movement in the 60’s. He also fought for gay rights and  freedom of speech. 

After he was denied a $5 raise at Esquire magazine, he left to start Playboy. At its peak, it had over seven million subscribers. Here are 15 of the hottest women Hef dated over the years. Cheers to you playboy.

15. Donna Michelle

Model Donna Mitchell posed nude for Playboy and was Playmate of the Month way back in December of 1963, although her pictures could come out of any (nude) magazine today. She also ended up as the Playmate of the Year for 1964. Despite the fact that she was only 17 at the time her first pictorial was shot — which was illegal.

After that, she studied ballet and danced in the New York Ballet while studying in college.Ultimately, she thought acting was the better career pursuit for someone with her talent. She also got married at the age of 17 and ended up getting a divorce from her husband David M. Ronne when she was about 21 years old.

She passed away in 2004 at the age of 58 but her pictures will live on forever. Even if looking at them now may end up putting you in jail.

14. Holly Madison

Holly Madison was perhaps the most well known girlfriend from the E! TV show in the early 00’s — The Girls Next Door, which also starred Hef himself. She began dating Hef in 2001 and was his main girlfriend for a pretty long time.

Surprisingly, Madison was never actually a Playmate herself, just like the other two members of the show — Kendra Wilkinson and Bridget Marquardt. She then turned on Hef after they broke up — especially after Hef got engaged to Crystal Harris.

The reality TV star released a tell-all book about her life with the Playboy mogul that wasn’t flattering at all. 

13. Sondra Theodore

Sondra Theodore represented the late 70’s era of Playboy and was a true natural beauty, one of the final ones before breast implants and bad perms became the norm — although Playboy did avoid that trend for the longest time.

One of the main parts of her allure, outside of the fact that she was naturally gorgeous was that she was a Sunday School teacher. If she was teaching you about God you’d probably believe in him too.

The 70’s were all about the continued sexual revolution that began in the 60’s.  Her portrait was front and center on the late 70’s version of the classic Playboy pinball machine.

12. Bridget Marquardt

The least popular of the Girls Next Door stars, Bridget Marquardt perhaps weathered that show better than the other two in terms of her reputation.  Marquardt mostly disappeared from the limelight. Like Madison and Wilkinson, Marquardt was never officially a Playmate herself, at least before she became one of his girlfriends for five years (from 2003 to 2008). She did end up in the magazine a bunch after that and that’s pretty much the last we’ve heard from her.

11. Crystal Harris

This may be a controversial choice as Crystal Harris was the woman who broke Hef’s heart when she left him at the alter. But that doesn’t detract from two things: that she eventually did return and marry Hef — after talking a ton of crap about him in the media, sure — but more importantly that Hef wanted to be with this woman bad enough to forgive her for everything.

So, she makes this list because of that and because she is a beautiful young girl who at least didn’t (originally) marry him just for his money. With him gone now you’d have to wonder what sort of prenup he made her sign to ensure she didn’t end up owning the magazine. Perhaps that’s what made her bolt in the first place.

10. Tina Marie Jordan

Playmate of the Month back in 2002, Tina Marie Jordan does remind you a bit of the 90’s super-fake-boobs and bleached blonde look that was synonymous with Playboy at the time. Considering those features, it’s perhaps not surprising that she dated Hef; she was the perfect example of his type —  his first wife was sort of a plain-jane brunette with 50’s era glasses though.

Jordan met Hef while she was attempting to obtain her license to practice real estate. She only starring in pictorials for the magazine after they started dating. She used to be a regular on the Howard Stern show and she even starred on the 7th season of VH1’s The Surreal Life — think Verne Troyer peeing in a corner from a mobilized cart.

9. Kimberly Conrad

 

Kimberly Conrad personified late 80’s beauties, whether in Playboy or otherwise. She took Playboy by storm in 1988 as the centerfold in January of that year and eventually the Playmate of the Year in 1989. It’s sort of funny to think that when he launched the magazine Hef had only been with one person, his wife at the time.

It was after she had an affair that he thought about branching out sexually, and boy did he. Conrad was Hef’s second wife. While they would later divorce, it perhaps should be lauded for how long it lasted: nine years together and two sons. One of those sons now runs the magazine and was responsible for temporarily removing nudity.

8. Brande Roderick

Brande Roderick exploded onto Playboy in 2000, after leaping into somewhat mainstream consciousnesses thanks to her role on Baywatch. After that, she became Playmate of the Month in April of 2000 and Playmate of the Year in 2001.

She’s perhaps one of the more famous Playmates; she had a semi-serious career starring in multiple films (Hollywood and Bollywood). She appeared in a saucy Starsky and Hutch scene as well as The Nanny Diaries. Either way she was the perfect women to transition Playboy into a new millenium.

And unlike Pamela Anderson — who personified the magazine in the early 90’s — Hef slept with her. While she is still a jaw-dropping beauty, she was a bit softer and more refined than a lot of the girls Playboy photographed in the late 80’s and 90’s, perhaps showing return to the type of girl (aka the real girl) that made the magazine famous in the first place. 

7. Kendra Wilkinson

The best looking of the original crop of Girls Next Door was never actually a Playmate and only posed in the magazine after the show blew up. She is perhaps the most famous Playmate of the 00’s and also the most relevant still.

She has parlayed her time on Girls Next Door into her own reality show that chronicles her life as the wife of — sometime — NFL wide receiver Hank Baskett. Baskett is mostly known for fumbling the onside kick in the Super Bowl he played in and basically ruining the game.

A genuine person, her tenderness shined through on Girls Next Door and endeared fans to her. She was fiercely loyal to Hef, visiting him often on her reality show and to check in, especially after she struggled with her husband’s affair and needed someone to talk to.

While it did become a sort of a creepy father/daughter sort of relationship, it did show that Wilkinson and Hef were good people at the end of the day.

6. Izabella St. James

Izabella St. James was another member of this list that was neither girlfriend nor wife at any point. Despite that, though, she did achieve one major and historic Playboy feat: she was the first Bunny to write a book. Titled Bunny Tales: Behind Closed Doors, her book was a tell-all about the lifestyle at the Mansion that are often not the most flattering.

St. James wrote about the two and a half years stay she stayed at the Playboy Mansion. She said that despite that time, she only hooked up with Hef once for about 15 minutes. She’s an intelligent woman who has a degree in law and has since returned to her home country of Poland to capitalize on her fame and star in reality shows.

5. Barbi Benton

Barbi Benton began her Playboy career at the age of 18 as the co-host of the entertainment show Playboy After Dark alongside Hef himself. He asked her for a date when he was 42 and she was 18 — which is actually good for Hef, who married Crystal Harris when he was 85 and she was 26.

Like most girls, Benton didn’t mind the age difference and they dated for a number of years during the prime era of Playboy— often referred to as the Barbi Days. She was on the cover four times, from July 1969 through December 1985 but never achieved Playmate status.

She may be one of the longest serving models the magazine has ever had, though. That nearly two-decade career landed her roles in movies and even a career as a country singer. She’s got the perfect name for it!

4. Carrie Leigh

Perhaps outside of Kimberly Conrad no other model personified the 80’s like Carrie Leigh. She was in the magazine quite a bit especially at the earlier part of the decade. She was never considered a “girlfriend” of Hefner but she did grace the magazine cover so many times she became known just for that.

She also was widely known as Hef’s lover even if she was never elevated to girlfriend, nor did they ever get married. Hef did refer to her as his “baby boo-boo,” which considering their age difference at the time probably wasn’t the best decision.

Despite the lack of labels on their relationship, she sued Hefner for palimony after their break-up. She used the money she “won” to start a magazine of her own, titled Nude.

3. Shannon Tweed

One of the more famous entries on this list, Shannon Tweed, yet another blonde bombshell that dated Hef in the 80’s. Originally from Canada, Tweed was the centerfold in the November 1981 issue and Playmate of the year in 1982. She made an even  bigger name for herself starring in erotic cinema.

She is perhaps now more well known for being married to Kiss bassist and overall creep, Gene Simmons — the guy with that Tongue. Tweed starred alongside him on the E! reality show Gene Simmons Family Jewels back when giving aging rockstars reality shows about their family captivated the nation.

2. Karen Christy

Karen Christy almost nabs the top spot on this list not only because she was a natural beauty — and maybe the biggest ‘It’ girl the magazine had in the 60’s — but because she gave Hugh Hefner his most “passionate relationship,” according to the man himself.

She’ll be a legend forever, remembered as the woman who gave Hef what he desired the most. Perhaps it was because of the thrill of it all; their relationship was one of the few affairs Hef ever embarked on — he always had like five girlfriends so why cheat?

At the time he was dating another famous former GF of his, Barbi Benton. He would see Christy at his Chicago offices or whenever he was traveling. Time magazine busted them and revealed the affair to the world. While it was a sad situation, Hef probably didn’t regret it much.

1. The Shannon Twins

There’s a double mint gum joke here somewhere; the Shannon Twins top this list. Sisters Kristina and Karissa Shannon are identical twins and became famous when they replaced the original three girlfriends — Holly, Kendra and Bridget — on the much-talked about E! Show The Girls Next Door.

They were also Playmates in their own right, released as a double edition for July and August of 2009 — both girls being the Playmates for both months.

After they left the Mansion in 2010, Karissa went on to star in what must’ve been the world’s worst sex tape — with Spencer Pratt and Heidi Montag. And then again with her then-boyfriend in a video released by Vivid Entertainment with her then Boyfriend.

They also featured on season 9 of Celebrity Big Brother UK. They hit their peak in the mid-00’s and, arguably, Hef did too.

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