Hugh Hefner and Holly Madison: A Complicated, Bitter History

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When the news first broke that Hugh Hefner had died, our first thought was to wonder what Kendra Wilkinson had to say

Our second thought was of Holly Madison and her long, very complicated history with Hef.

A lot of people have bitter relationships with an ex, but this was ... much more involved than that.

Holly and Hef Photo

Starting at the age of 20, Holly Madison became one of Hugh Hefner's girlfriends, moving into the Playboy Mansion in 2001.

This relationship would last for seven years.

During that time, Holly Madison became a reality star on on the E! series, The Girls Next Door.

She costarred with Kendra Wilkinson, who went from being her frenemy to her full-blown enemy after she parted ways with Hef.

During her relationship, though, on camera and on the surface, everything seemed great for Holly Madison.

Holly has since revealed that she was miserable and suffering throughout. 

Holly Madison Attends Launch of of Jennifer Lopez's residency 'JENNIFER LOPEZ: ALL I HAVE' at Planet Hollywood Resort & Casino

In her book, Down The Rabbit Hole, Holly Madison describes her experience within the Playboy Mansion as anything but idyllic.

First of all, her initial impression was that being Hef's "girlfriend" wouldn't involve having sex with him.

We don't know exactly how she came to believe that, but she learned that it was not the case.

Her first night having sex with Hugh Hefner apparently involved his other "girlfriends" arranged around him while he, by her description, used marijuana and masturbated while pornography played on two large televisions in the room.

Hef even allegedly offered Holly quaaludes, which he referred to as "thigh-openers."

Now, some of that may sound like a little much (seriously, who needs porn playing on two different televisions? And the bit about the quaaludes offer is creepy), but that's all fine for consenting adults.

What's definitely not fine is the competitive culture in the Playboy Mansion that Holly says that Hef actively encouraged and fostered, where the girlfriends competed with each other for his favor.

What's worse is that Hef allegedly made a habit of reducing his girlfriends to tears by talking down to them and being genuinely hurtful.

(Some have pointed out that a common abuse tactic is to dress people down with emotional abuse so that people try harder to please you and so that your praise has more impact)

There's nothing wrong with polyamory, and plenty of people have healthy relationships despite massive age differences. But what Holly Madison describes having experienced doesn't sound healthy in the slightest.

Holly Madison, Hugh Hefner, Sheila Levell

Critics point out that Holly Madison must have been pretty good in that "competitive culture," because she spent a lot of her seven years in the mansion as Hef's "#1" girlfriend.

Others point out that Holly had sought a marriage to Hef and children with him, and that his refusal to marry her and his physical inability to father children with her made her feel rejected.

They say that the rejection made her bitter, and that this is why she has since blasted Hugh Hefner and her time in the Mansion.

Hugh himself accused Holly of having simply fabricated her negative experiences in order to cling to fame.

And, obviously, Holly's criticisms of that time are the primary source of her long-standing feud with Kendra Wilkinson.

Holly Madison and Hugh Hefner Photo

Overall, Holly Madison isn't the only voice that's spoken out to criticize Hugh Hefner.

His decision to buy a plot beside Marilyn Monroe is widely regarded as, well, super creepy.

Especially considering that Hef launched his magazine after purchasing nude photos that Marilyn had taken when she was a broke teenager. He published them without giving Marilyn herself a cent.

At the time, she worried that it would ruin her career.

Plus, there's the fact that, despite Hef's verbal push for racial equality and gay rights, so much of Playboy was dominated by blonde white women who catered to male consumers.

Holly Madison didn't make Hugh Hefner controversial. She just added her voice and very intimate knowledge of him to a chorus.

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Hugh Hefner Biography

Holly and Hugh
Hugh Henfer is the envy of millions of men around the world. Despite not being close to a spring chicken, the Playboy founder has a... More »
Chicago, Illinois
Full Name
Hugh Marston Hefner