5 Wild Hugh Hefner Stories You Won't Believe Are Real

Hugh Hefner, the man who began the Playboy media empire and known around the world for living a life of luxury and love that most men can only dream of, has died. He was 91.

By the 1960s, Hefner became the stuff of legend. The parties thrown at his Playboy Mansions in Chicago and Los Angeles were notorious for being drug-fueled orgies with Hefner in the center of it all, wearing his iconic silk smoking jacket. For decades to come, he would never be spotted without a bevy of beautiful women surrounding him, having multiple girlfriends at a time living with him in his palatial estate.

But it wasn’t all parties and sex in Hefner’s life, and some of the stories that came from female reporters who infiltrated the Playboy Mansion are downright disgusting.

Here are five of the more insane stories to escape the Playboy Mansion.


Made His Kids Stay With A Bunny When They Visited

via Crystal Hefner on YouTube

Although his children from his first marriage were all grown up at the time, his second marriage to Kimberley Conrad resulted in two more kids—Marston and Cooper—who’s arrival would transform the Mansion into a family homestead.

At least until Hugh and Kimberley split in 1998. Then it was back to his devious ways while the kids stayed with mom in a house down the street. But the kids would visit every once in awhile, and when they did, they’d shack up in a Bunny’s room. Room number three, to be exact, which had three beds, a private bath, and one of Hugh’s many girlfriends’s already living there. Yeesh.


Every Night A Group Orgy - Sort Of

via intouchweekly.com

The Playboy Mansion had a bizarre set of rules for the women who stayed there. There was a 9 p.m. curfew, the Playboy Bunnies weren’t allowed to have other boyfriends (although they often did), and perhaps strangest of all would be the nightly orgies that took place in Hugh’s bedroom.

Well, sort of. Here’s how a former Bunny describes the scene: "Two huge television screens projecting graphic porn lit up the otherwise dark bedroom. In the middle, a very pale man was tending to his own business...The girlfriends, in various stages of undress, were sitting in a semi-circle at the edge of the bed."


Hef Would Screw With His Bunnies In More Ways Than One

Hugh 1970
via npr.org

The nightly sexcapade was just one of the rules in the Playboy Mansion, but none of them were set in stone. Often Hefner would mix up the rules to favor one Bunny over another, turning the whole thing into more of a constant cat-fight.

There are tales of women stealing from each other, fighting over rooms and, of course, who would have Hefner's affection. He’d tell one girl that he hated how she wore red lipstick while saying to another that he loved the very same red lipstick that she wore. He also gave each Bunny a $1000 allowance for new clothing, but would sometimes withhold it if he felt she wasn’t “giving enough” in the bedroom. By all accounts, it was all the worst aspects of sexual servitude and living in a prison all rolled into one.


When Holly Madison Moved In The Carpets Went To Crap - Literally

Holly Madison
via thesun.co.uk

Although never a playmate, Holly Madison is a renowned for her appearance on The Girls Next Door, Hefner’s reality TV show. For a time she’d be the “number one” girlfriend of Heffner’s, eventually being asked to move into his own bedroom.

The only problem was Holly had a pair of dogs that were never housebroken, and would constantly crap on the carpets. The already decades-old carpets weren’t in great shape to begin with—what with the constant partying and whatnot—and having a pair of dogs pooping on them hardly improved matters. Hefner would often be seen waking up in the morning picking up turds.

He Lived In His Playboy Mansion Even After He Sold It

via architecturaldigest.in

In January 2016, Hefner put his Los Angeles Playboy Mansion up for sale (He sold his Chicago mansion in 1989) to the tune of $200 million. The catch? Hefner was contractually obliged to still live and “work” there until his death.

That might not sound like a particularly healthy living arrangement, but apparently, Daren Metropoulos, billionaire investor and philanthropist, felt otherwise. He didn’t actually live there while Hugh was still alive, and now that he’s passed on, the plan is to renovate and restore the Mansion to its original glory.


This Replica Lamborghini Costs A Fraction Of What The Real Thing Is Going For

More in Buzz