Since Playboy’s inception in 1953, many have had strong opinions about the publication, ranging from calling Hugh Hefner the “devil” to praising the publication as a “feminist outlet.” In recent years, more allegations have come up about the deplorable conditions and alleged abuse to which Playboy Bunnies and Playmates — as well as many of Hugh Hefner’s exes — were subjected. With the new A&E 10-part docuseries Secrets of Playboy, we’re taking a look back at some of the most famous women with access to the Playboy mansion over the years.
But first, a quick vocabulary lesson: While you might think that “Playboy Bunny” and “Playmate” are the same thing, they’re actually very different. Per Business Insider, a bunny is an employee whose job description includes serving and hostessing Playboy Clubs as well as the mansion. Playmates, on the other hand, are centerfold models, given lifelong titles like “Playmate of the Month” or “Playmate of the Year.” Many, many famous women have posed for Playboy over the years — but only bunnies, Playmates, and those with personal relationships to Hugh Hefner appear to have gotten close enough to see what was really going on for the women whose livelihood was inextricably linked to Hefner’s empire.
For example: Despite not being bunnies or playmates themselves, Hefner’s exes like Holly Madison and Bridget Marquardt have seen everything in the Playboy world, and they’re ready to tell their tales. Madison has been very vocal about how deplorable the Playboy empire is, revealing she even considered suicide after her time there, and Marquardt is speaking out in this year’s docuseries.
From those who are coming forward with allegations about Playboy to those who remember their time with the brand fondly, let’s look back at the women with the longest Playboy histories below.
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Holly Madison
Image Credit: James Atoa/Everett Collection. Despite never being a playmate or bunny, Holly Madison was very entrenched in the Playboy life, especially since she was Hugh Hefner’s “main” girlfriend. She was one of the stars of Girls Next Door, a show that followed Hefner’s girlfriends, which eventually led to a nude spread in the Nov. 2005 issue of Playboy. Madison has been a huge part of exposing the Playboy mansion and Hefner, alleging that he abused her and gave her Stockholm Syndrome. She details it all in her bestselling novel, Down the Rabbit Hole: Curious Adventures and Cautionary Tales of a Former Playboy Bunny.
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Sondra Theodore
Image Credit: Ralph Dominguez/MediaPunch /IPX. Sondra Theodore is a former Playboy Playmate who was named Playmate of the Month in the July 1977 issue; she’s also one of Hugh Hefner’s ex-girlfriends, and one of the women bravely speaking out in A&E’s new docuseries Secrets of Playboy. In the series, she alleges that the late Hefner “groomed” her after first meeting her at age 19 and eventually having her move in with him. Per an interview with Fox News, Theodore further detailed heartbreaking allegations of how Hefner broke down her boundaries: “I was groomed. It was a slow grooming to get to that point. And he broke me. He kept on and on about it. Finally, I made a deal that I would try it once and if I didn’t like it, he couldn’t make me do it anymore. You know, just leave me alone about it. Before then, every time he would ask, I would say, ‘Never, it’s never going to happen. It’s never going to be part of my world.'”
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Bridget Marquardt
Image Credit: Priscilla Grant/Everett Collection. Like Holly Madison and Kendra Wilkinson, Girls Next Door alum Bridget Marquardt was neither a bunny nor playmate, but one of Hugh Hefner’s exes. Like Madison, Marquardt has spoken out about the alleged abuse Hefner put the girlfriends through, most recently in A&E’s Secrets of Playboy. Even her participation in Girls Next Door was under duress, she describes on the show.
“I was in the shower and all of a sudden Hef is standing there. He opens up the shower door like, ‘Why aren’t you signing this contract? I need you to sign this contract!'” Marquardt recalled. “I signed the contract, crying and soaking wet.”
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Kendra Wilkinson
Image Credit: Priscilla Grant/Everett Collection. Unlike her fellow Girls Next Door alums, Kendra Wilkinson hasn’t shared allegations of mistreatment when asked about her Playboy days. After her time in the Playboy mansion, Wilkinson went on to welcome two children into the world and continue her television personality work, most recently with a new real estate show Kendra Sells Hollywood.
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Crystal Hefner
Image Credit: Priscilla Grant/Everett Collection. Crystal Hefner is both a former Playboy Playmate and the widow of Hugh Hefner. They married on New Year’s Eve in 2012 and were together until his death in Sept. 2017.
On Jan. 24, 2022, Crystal backed fellow Hefner ex Holly Madison’s claims that Hefner took many explicit photos of the women he spent time with without their consent. Crystal took to Twitter after Madison’s claims became public, writing, “I found thousands of those disposable camera photos you are talking about @hollymadison. I immediately ripped them up and destroyed every single one of them for you and the countless other women in them. They’re gone.”
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Jenny McCarthy
Image Credit: Priscilla Grant/Everett Collection. Jenny McCarthy’s career actually started at Playboy back in 1993, with her becoming a centerfold model not soon after, and earning the title of Playmate of the Year in 1994. Her centerfold, however, went on to cause her problems in her personal life. Hefner opted for a “sexy schoolgirl” theme for her shoot given her devout Catholic upbringing, and McCarthy’s family did not react well to the news.
In 2012, McCarthy told ABC about the fallout she knew was coming from the moment she landed the centerfold: “Hef said, ‘You’re Playmate of the Year.’ I went, ‘Oh my God, yes,’ and, ‘Oh my God, no.’ I literally went to my car and cried. I cried for about an hour that I was Playmate of the Year.”
“My mom was the one that was like … ‘I only have three daughters now,'” she continued. “I begged her. I was like, ‘Listen, you raised me to be a good person. This was my only option to get out there. I will be a Playmate that does something great, mom. Trust me and stand by me.'”
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Bonnie Halpin
Image Credit: AP Photo/Edward s. Kitch. Deemed the first-ever official Playboy Bunny, Bonnie Halpin was the first “door bunny” who greeted people into the Playboy Club back when it opened in 1960. She also appeared on the cover of the October 1962 issue of Playboy, and went on to have a wide-ranging career as a marathon runner, volunteer, and personal trainer.
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Jayne Mansfield
Image Credit: Everett Collection. Old-Hollywood star Jayne Mansfield appeared a few times in Playboy magazine and even in the calendar, and was named Playmate of the Month in Feb. 1955. In a dark turn of events, her first husband Paul Mansfield tried to get custody of their daughter (Jayne Marie Mansfield — not her other daughter, Mariska Hargitay) on the basis that Jayne was an “unfit” mother for appearing in Playboy, per Grunge. Good news: he lost)
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Pamela Anderson
Image Credit: Steven Ferdman/Everett Collection. Pamela Anderson appeared on not one, not two, but 14 total Playboy covers ― making her the record holder for most covers in the magazine’s history. The Baywatch alum appeared on covers from 1989 all the way until 2016.
In a 2018 interview with Piers Morgan (via The Sun), Anderson looked back on her time at the Playboy mansion and her glimpses inside what life looked like for the women who lived there: “Everyone was naked in the grotto and the girls were downstairs and they all went upstairs. I followed them upstairs. I thought, ‘What could be going on up here?’ Seven girls, one at a time with Hef. I stood at the end of the bed watching them and then I realized they were watching me. I thought, ‘This is not a movie. I need to leave.'”
“I have seen a lot of craziness at the Playboy Mansion,” Anderson added. “He had a lot of women around. There were these big TV screens with crazy things going on with him and the girls and baby oil.”
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Marilyn Monroe
Image Credit: Everett Collection. Marilyn Monroe was the first-ever Playmate — well, technically, she was the first and only Sweetheart of the Month, with each woman being named Playmate of the Month after that first edition in 1953.
Here’s the thing, though: Monroe never posed for Playboy or consented to her photo being on the cover. George Barris’ book Marilyn: Her Life in Her Own Words, via Biography, revealed not only that Monroe hadn’t consented to Hefner using four-year-old images ― and that Hefner never paid her — but that she’d only gotten the photos taken because she desperately needed the money.
Monroe told Barris the photos were originally taken in 1949 with photographer Tom Kelley, under the agreement that Monroe would look unrecognizable, and said this about why she hid her name.
“I was nervous, embarrassed, even ashamed of what I had done, and I did not want my name to appear on that model release.”
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Debbie Harry
Image Credit: Steve Mack/Everett Collection. Blondie frontwoman Debbie Harry worked as a Playboy Bunny for five whole years from 1968 to 1973. But when she met guitarist Chris Stein in 1973, she hung up the bunny ears for a rocking future.
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Ines Rau
Image Credit: Sipa via AP Images. Ines Rau made history by being the first openly transgender Playmate, named as Playmate of the Month in Nov. 2017. In an interview with People, Rau said, “When I was doing this shoot, I was thinking of all those hard days in my childhood. And now everything happening gives me so much joy and happiness. I thought, ‘Am I really going to be a Playmate—me?’ It’s the most beautiful compliment I’ve ever received. It’s like getting a giant bouquet of roses.”
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Gloria Steinem
Image Credit: AP Photo/Robert F. Bukaty. Feminist icon Gloria Steinem took it upon herself to go undercover as a Playboy bunny and expose what was going on there in the 1960s. The explosive essay, “A Bunny’s Tale,” ran in the Jan. 1963 edition of Show Magazine, and exposed the underpaid hours, degrading tasks, and overall poor conditions fellow Bunnies faced.
She told People that she knew the act was dangerous, but she wanted the story to be told. “I finally just decided I had enough notes and so on. But you also have a relationship with the women you’re working with… And they had mostly sad stories,” she shared.
Steinem goes in-depth on this experience in her 2019 book The Truth Will Set You Free, But First It Will Piss You Off!
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Anna Nicole Smith
Image Credit: Michael Germana/Everett Collection. Anna Nicole Smith, like many Playmates before her, was a one-time Playmate of the Month (May 1992) and went on to be named Playmate of the Year in 1993. While she originally used the name Vicki Smith, she soon took on the stage name Anna Nicole Smith.
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Heather Rae Young
Image Credit: Derek Storm/Everett Collection. Selling Sunset star Heather Rae Young was named a Playmate quite recently, in 2010 to be exact. She’s said that she sees her time at Playboy as being a pivotal point her career, telling The Sun: “It catapulted my career, it changed my life, it was the most defining moment in my life. I don’t regret anything I’ve ever done. I’m proud of my life. Everything I’ve done has got me to where I am today.”
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Kathryn Leigh Scott
Image Credit: Everett Collection. Before her soap opera career took off, Kathryn Leigh Scott spent three years working as a Playboy Bunny. After her entertainment career, she launched a publishing company called Pomegranate Press, Ltd, where she published her own book called The Bunny Years, which goes in-depth on the women in Playboy.
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