Inside Hugh Hefner's Empire and the Bizarre Rules Women Have to Follow at the Playboy Mansion

In the Playboy Mansion, owned by Hugh Hefner, women lived under strict rules. One of the strangest rules was the imposed curfew. Women had to be home by 9 p.m. every night. Crystal Hefner, Hugh's wife, had it even tougher. She said, "I feel like I was very restricted. I think a lot of it was very hard for me, he didn't want me out past 6:00 p.m., so I was home before dark most days."

Hugh also controlled how the women looked. Red lipstick was a big no-no. Holly Madison, one of Hugh's ex-girlfriends, shared on a podcast that Hugh associated red lipstick with older women and hence prevented his girlfriends from wearing the shade. Bridget Marquardt, another ex-girlfriend, revealed, "[Holly] came down with red lipstick one time, and he flipped out and said he hated red lipstick on girls [and to] take it off right away."

Perhaps the most controversial rule was the expectation of intimate relations with Hugh. Many women have spoken about the same, describing group encounters and the use of drugs. Kendra Wilkinson, a former girlfriend, admitted, "I was usually very very drunk doing those evenings, I tended not to care about much until the next day. I had to be very drunk or smoke l lots of weed to survive those nights." Blonde hair was strongly preferred. Crystal shared the pain of maintaining this look. "So I'd have to go bleach it and it would burn my scalp and I'd have blisters. But for some reason, I thought this was all normal and that's what it meant to be seen as beautiful in Hef's eyes."

While Hugh dated multiple women, his girlfriends weren't allowed to date anyone else. Madison revealed, "When I first moved in, six other women were living there, and a lot of them were dating other people on the side. They weren't supposed to. That was against the rule and Hef was super jealous." The women received a weekly allowance of $1,000. Hugh once admitted, "That part is true. If you write it and make it sound sleazy, that's easy to do. But the girls got a clothing allowance," as per The Daily Beast. Some women reportedly also had to sign non-disclosure agreements.

Even small details like nail polish were controlled. Crystal shared, "Our nail polish couldn't be anything but some neutral color, no French manicure." Getting ready for parties was an all-day affair, with strict guidelines on appearance. During parties, the women had to stay close to Hugh. Madison explained, "We would be expected to sit with Hef at his table for the entire time. It was heavily discouraged sneaking off on your own to socialize." Holidays were always spent at the Mansion. Madison wrote in her book, "Christmases were always spent with Hef. Girlfriends were given 'off' days before or after the holiday to visit family and friends, but there were no exceptions for the actual day itself," as per The List.