Tag Archives: Hugh Hefner

See Playboy’s First Transgender Model

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In the early 1980s, Caroline “Tula” Cossey was living the dream of every aspiring model. She was cast to play a Bond girl in the film For Your Eyes Only alongside Roger Moore. To accompany the film’s release, she appeared in a spread forPlayboy, featuring her and other Bond girls from the film.

Then, just as the Bond movie came out, a tabloid called News of the World outed Cossey against her will in a headline that read “James Bond Girl Was a Boy.” The tabloid’s headline sparked a media firestorm and Cossey was thrust into the spotlight as a trailblazer. She instantly became a role model for trans women. Since then, Cossey carried on with her acting and modeling, making it into the pages of Playboy once again in 1991 as well as penning two autobiographies.

In a new interview with Playboy about her groundbreaking career, Cossey, 60, (who now lives in suburban Atlanta with her second husband) said she was born as Barry Cossey and spent much of her life knowing that she was a woman. She completed gender-reassignment surgery in 1974 after years of other surgeries and treatments. In the 70s and 80s, she pursued her dream of modeling, appearing inHarper’s Bazaar and Australian Vogue. She also found fame as a “Page Three Girl,” a model in the pages of British paper The Sun.

Play Boy’s Holly Madison on Hugh Hefner: “I Was Constantly Made to Feel Ugly”

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Holly Madison’s new book Down the Rabbit Hole shows off the unglamorous side of the Playboy world.

When it comes to empowerment stories, you might not expect one to start in the Playboy Mansion, but Holly Madison’s does. Before Madison became the “Number 1 Girlfriend” of Playboy founder Hugh Hefner, she grew up in a small town of 10,000 with big dreams of becoming an actress like her idol, Marilyn Monroe. But soon after she arrived in Hollywood, at age 22, her life took a detour when she met Hefner, the “notoriously lecherous 70-something old man who offered me Quaaludes that he referred to as ‘thigh openers.’”  It’s a moment, Madison, now 35 wishes she could do over. “Are you kidding me?” she writes in her revealing new memoir Down the Rabbit Hole. “ Why didn’t I run for the nearest exit?”

Instead, Madison got caught up in the myth of the Playboy mansion and becoming a Bunny. About to be kicked out of her apartment, the mansion offered a solution on where to live rent-free, and she hoped that Playboy could launch her career. It did, but there was a big price to pay. Madison went from being a confident, happy girl to insecure and deeply depressed. She even developed a nervous stammer. At one point she told Hefner she wanted to see a psychiatrist and he told her to talk to his secretary instead. He knew a therapist would tell her to pack her bags.

A constant rotating cast of women, all vying for Hefner’s attention and weekly $1000 clothing allowance, created a nightmare mean-girl scenario. Plastic surgery was paid for, along with salon appointments. It was all designed to have the women looking like clones—platinum blonde, booby, with perky “baby” features. When Madison tried to assert some individuality and cut her hair into a bob and wear red lipstick, Hefner told her she “looked old, hard, and cheap.” The experience made her feel “beyond ugly…maybe I was just the homely girl who was ‘lucky’ enough for Hef to allow into the mansion.”