Holly Madison's Harmless Beauty Decision Had Hugh Hefner 'Screaming'—He Called Her 'Old, Hard, and Cheap'

Holly Madison and Hugh Hefner were some of pop culture’s most famous couples in the early 2000s. Madison, who was the star of the E! reality series The Girls Next Door, seemed to have it all—money, looks, fame, and the love of Hefner, the wealthy founder of the Playboy empire.

However, the two broke up in 2008, and in recent years, Madison has been open about the true nature of her relationship with Hefner. In an upcoming docuseries, Madison is getting more real than ever, admitting that Hefner sought to control her appearance and control even small aspects of her beauty routine.

Holly Madison is the most famous of Hugh Hefner’s girlfriends

When Madison met Hefner in 2000, she was an aspiring model who had dreams of bigger things. She met Hefner by chance at a party at the Playboy Mansion, and her good looks caught Hefner’s eye.

After spending the night together, Madison asked Hefner if she could move into the Playboy Mansion and he agreed. She became his “number one” girlfriend, and her star rose even higher after she started appearing on the reality series The Girls Next Door, which presented a glamorized version of life at the Mansion.

No one watching the show could have known that behind the scenes, Madison was miserable. As she revealed in her 2015 biography, and again in the all-new docuseries, Secrets of Playboy, Madison’s relationship with Hefner was toxic and unhappy. 

What did Hugh Hefner say to Holly Madison after she cut her hair short?

In Secrets of Playboy, Madison opened up about how Hefner sought to control her looks and appearance. As reported by Insider, Madison admits in the docuseries that “I got to a point, not too far into my time there — I think it was, like, six months in — where I kind of broke under that pressure being made to feel I had to look like everyone else.”

Madison said that she decided to get her long hair cut short, but that Hefner hated her new look. “I came back with short hair, and he flipped out on me. He was screaming at me and said it made me look old, hard and cheap.” Another of Hefner’s girlfriends at the time, Bridget Marquardt, revealed in the series that the Playboy founder hated red lipstick on women and that he verbally berated Madison when she came downstairs one night wearing red lipstick. 

Holly Madison is now a bestselling author and reality star

Eventually, Madison broke free from life at the Playboy Mansion, ending her romance with Hefner in 2008. After leaving Hefner, Madison embarked on her own career, appearing on other reality shows like Dancing with the Stars and headlining her very own burlesque show.

Madison has also opened up on numerous occasions about life behind the curtain at the Playboy Mansion, releasing a bestselling biography in 2015 and sharing details on her YouTube channel about how her Playboy career wasn’t all sunshine and rainbows.

These days, Madison is not only a social media influencer and bestselling author – she’s a mom as well, to two young children that she shares with her ex, Pasquale Rotella. Although Madison’s journey to stardom has not always been easy, the star has worked hard to dispel the rumors about life inside the Playboy circle – and fans can catch her dishing even more on the upcoming A&E docuseries, Secrets of Playboy, which will premiere on the network in January 2022.

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