Celebs You Didn't Know Posed For Playboy

When Hugh Hefner printed his first issue of Playboy in 1953, the cover featured none other than Marilyn Monroe. The Chicago-based magazine soon reached subscribers all over the world and Hefner took himself and his satin pajamas to California, where he purchased the now-famous Playboy Mansion, located in the Holmby Hills area of Los Angeles.

Everything about Playboy became iconic. Hefner's 29-room house boasted not only a zoo but wild parties and a rather imperative gate to keep the uninvited out. The Playboy Mansion was a symbol of hedonism and an end to puritanical views on sex in America. The bunny became a ubiquitous symbol in consumer culture, branding everything from Zippo lighters to reading glasses. (Hey, how can you enjoy the centerfold if you can't see it?) The magazine itself became a central discussion around sexuality and feminism. Meghan Murphy, founder of the "Feminist Current," said at the time of Hefner's death that he was a "billionaire who profited from women's subordination," per The New York Times.

While the publication has its fair share of detractors, there are some who've perceived it as a tool of female empowerment. Either way, there's one thing that we all can agree on: There have been a lot of famous faces on the cover of Playboy. Let's get into some of the celebrities you might not have known posed for the magazine.

American supermodel Cindy Crawford appeared on the cover of Playboy in July 1988 and again in October 1998. For both covers, she was photographed by famed fashion photographer Herb Ritts. The collaboration between subject and photographer was a brilliant one. Ritts was famous for his ability to capture both the "bold" and the "sensual," as the Museum of Fine Arts in Boston explains. Even more suitable for Playboy, Ritts was famous for "celebrating the human body and embracing the carefree California lifestyle" in his work. Oh, and as Vanity Fair recounted, the photographer introduced the model to actor Richard Gere. Crawford and Gere married in 1991 and divorced a few years later. 

So how does Crawford feel about her Playboy modeling gigs now? "I look back at some of my old Playboy pictures and I think, 'Why wasn't I walking around naked all the time?'" she told Net-A-Porter in 2019. Crawford admitted that even decades later, she's still a fan of appearing naked. She shared in the interview that she's in the buff in photographer Russell James' book "Angels," and saw the decision as an uplifting one. "Part of the reason I wanted to do it was that I thought, at what age is being naked not beautiful anymore? Is there a sell-by date on us?" Crawford asked. The answer, obviously, is no.

Lindsay Lohan was Playboy's cover girl for the January/February 2012 issue, and on the cover, she sports blonde hair and wears nothing but heels as she sits backwards in a Playboy bunny logo chair. Lohan's presence in the magazine came at a contentious time in her life. Just before the magazine's release, Lohan was arrested in 2011 "for violating probation on drunken driving and theft charges," according to Reuters.

Despite the evolving legal issues, Lohan's spokesperson Steve Honig said, "The pictorial is absolutely fantastic and very tasteful, and will be accompanied by an interview that will let readers see another side of Lindsay." The aesthetic vibe of her shoot was very nostalgic of the iconic Marilyn Monroe shoot in 1953, as the Daily Mail pointed out, with both stars wearing their hair in blonde curls and velvet red as the backdrop. But Playboy had to shell out some cash to land Lohan. According to TMZ, the mag offered her $750,000 and Lohan came back with a demand of $1 million. Evidently, LiLo accepted their counteroffer.

As MTV News reported at the time, the shoot was so highly anticipated that some of the photos were leaked online and Playboy had to take action. In an effort to spin a leak into gold, Hugh Hefner tweeted (via Daily Mail), "Because of the interest and the internet leak, we're releasing the Lindsay Lohan issue early. Lindsay Lohan was the top search name on the internet yesterday. Hot Hot Hot."

When Drew Barrymore was 19 years old, she was the cover for the 1995 January issue of Playboy. While Barrymore stressed that the decision to pose nude was for her, director Steven Spielberg, who worked with 7-year-old Barrymore on "E.T.," was less than impressed. "He still sees me as a child, makes me remove my lipstick when I go into his office," Barrymore told the Hollywood Foreign Press Association in 1995. "Wait till he sees me nude in Playboy. His scolding phone call!"

Despite this threat, Barrymore had nothing but positive things to say about her Playboy shoot. "It was like my own personal adventure," she went on. "I totally had a great time with it and I think I'm very comfortable in my skin and to me, the human body is a really beautiful thing." She added, "I'm not for extra gratuitous nudity but this was really interesting and a dare."

The legendary director's reaction went a bit beyond a phone call — but it sure sounds like it was all in good fun. As Spielberg and Barrymore recounted on an episode of "The Drew Barrymore Show" in 2021, he gifted her with a quilt that read "Cover Up" and used paper doll outfits to dress the "partially exposed photographs." As an "apology," Barrymore sent him a series of photos of herself in a nun's habit with captions that read: "I'm sorry," "I've seen the light," and "I'm on my way." 

British model and fashion icon Naomi Campbell was the cover girl for Playboy in 1999. Campbell was already a shining star at that point, having blown up earlier that decade. As Vogue France put it, Campbell "became a cult figure of the 1990s" and "an emblematic figure of the industry." On the cover, she's wearing white lingerie and a white furry coat against a pine green and bright red backdrop. As you might've deduced from the color scheme, it was the magazine's Christmas issue that year. Needless to say, it's all very festive.

The year after Campbell's issue hit the newsstands, she told Barbara Walters, "It took me eight years to say yes to Playboy. I mean, I don't think being nude is vulgar at all if it's done in an artful way."

Her feature in Playboy wasn't the last time Campbell went topless. As Daily Mail reported, when she became the face of NARS Cosmetics for Spring 2019, she posed sans blouse for the brand. She also lost her shirt in 2012 for Interview magazine's Russian and German editions alongside Kate Moss, per HuffPost. As usual, Campbell and Moss looked unbelievable.

Jerry Hall, ex-wife of Mick Jagger, and daughter Lizzy Jagger, have both posed for Playboy over the years. Hall appeared in the October 1985 issue after opting out of nudes earlier in her career. She told The Daily Telegraph that when she was 16, artist Salvador Dali offered her a part in one of his films, but it required "her to run naked through his sculpture garden." Hall wasn't ready for that, considering she was so young, and it sounds like she wishes the timing was different. "At that point I wasn't doing nude — my mum didn't want me to do nude — so I said no," she said. "But I really regret that. That would have been faaabulous." Clearly, Hall later changed her tune about posing nude.

Years later, daughter Lizzy appeared on the cover for Playboy's June 2011 issue and spoke about people's preconceived notions of her. "People assume that because I was brought up on Rolling Stones tours and my father is who he is, I'm some kind of rock-and-roll bad girl," she told the publication (via Page Six). "But I do like to have a bit of fun."

How did Lizzy's mom and dad feel about her appearing in Playboy? They were for it. "They understood that when you don't know when you're going to have kids, it's nice to have wonderful pictures of your 20-something self," Lizzy explained to the magazine. "And at 27, I feel comfortable expressing myself through my body." Like mother, like daughter.

In December 2018, Madonna shared a throwback photo on Instagram where she's posing naked. In the caption, she shared that when she was 19 and living in New York City, she worked as a nude model for art and photography classes "to pay the rent." She continued, "Many of these photos were sold to Playboy and Penthouse when I became famous." And this exposure was far from appreciated, as she felt she was "exploited" by those who took the photos and then she was shamed by "the Patriarchy ... for being naked."

As Complex recounted, Playboy released these photos in the September 1985 issue. While she was not thrilled with the way the pictures ended up at the magazine, she still appeared on the cover — but fully clothed. According to People, some of these throwbacks of Madonna, which were captured in 1979 by photographer Martin H.M. Schreiber, are included in the book "A Retrospective 1966-2014."

As Madge recollected in the aforementioned Instagram post, the photographs plus her statement ("I am not ashamed") led to a creative collaboration with Keith Haring and Andy Warhol. "You cannot stop Art by trying to Shame it," she wrote. "Creation always wins." You've got that right.

When Olivia Munn appeared in Playboy in the July/August 2009 issue, she negotiated for a clothed cover ... and still, wardrobe issues ensued. In her memoir, "Suck it, Wonder Woman!," Munn writes that she requested her own stylist for the shoot, but the photog evidently had a different plan. "I get a call saying that this photographer insists on using a different wardrobe stylist," she recalls before clarifying why she wanted to use her own: "I've had one too many bad experiences with so-called 'fantastic' artists and stylists and I didn't want the cover of Playboy to be something I wasn't proud of."

Munn explains that when she met the other stylist, the wardrobe choices were completely different from what she had agreed on. "Suddenly and quite horrifyingly, he pulls out — and I'm not making this up, I swear — a black, fishnet one-piece bathing suit where you can see everything going on," she recounts. The teams went back and forth about what she would and wouldn't wear, and ultimately, Munn got the non-nude shoot that she was originally promised.

"I think there's nothing wrong with Playboy — there's nothing wrong with women who want to be in the magazine, if they're comfortable being naked and showing everything," Munn told Kotaku. "There's nothing wrong with it, it's just not something I'd do."

Model and burlesque dancer Dita Von Teese landed the cover photo for Playboy's December 2002 issue. Born Heather Renée Sweet, Von Teese's full stage name actually came about thanks to her Playboy shoot — and a fortuitous mistake. As she told Vogue, she'd used the name "Dita" for many years, inspired by actor Dita Parlo. When she posed for Playboy in the '90s, they asked her for a last name, so she flipped through a phone book. "So I found the name Von Treese and I called Playboy and said, 'I'm going to be Dita Von Treese,'" she recalled. They accidentally used "Teese" instead, and the rest is history. 

"I left it because I didn't really care," she told Vogue. "I didn't know I was going to go on to trademark it all over the world! I had a laugh once when somebody once said, 'Oh, her name is so fabricated.' And I'm like, 'It's a typo!'"

When Playboy briefly decided to stop using nude photographs in its issues in 2015, Von Teese had some feelings. She told Elle. "On one hand, I don't really know what the point is if they don't have nudes. ... I think it's sad that that kind of photography might go away." The magazine returned with nudes in 2017.

As an up-and-coming movie star, Sharon Stone saw a spread in Playboy as a chance to rocket her career, and she was totally on the nose. In 1990, Stone posed for the magazine in the hope that it would land her a filmography-defining part. "I'm more of a logic person and a strategy person," Stone said on "The Drew Barrymore Show" in 2020. "Even when I wanted 'Basic Instinct,' I decided that I was going to do a Playboy article, specifically because I wanted to get this film." Evidently, her strategy worked. 

A few years after she posed in Playboy, she chatted with the magazine about how the flick changed both her professional life and personal life. "'Basic Instinct' completely rocked my world," she said in a 1992 issue. "People started chasing me down the street, hiding in my car, showing up at my house. Unbelievable. I've hidden under the counter in the kitchens of restaurants." She said the "sudden fame" that she'd experienced could be "overwhelming" and "scary" at times. 

Her sex symbol status has stuck, to say the least. When Oprah asked her about the "pressure" that comes with being a sex symbol in a 2014 sit-down, Stone replied, "It's a pleasure for me now. I'm going to be 56 years old, if people want to think I'm a sex symbol, it's like, yeah!"

Actor and "The Real Housewives of Beverly Hills" star Garcelle Beauvais appeared on the cover of Playboy in August 2007 when she was 40 years old. "I thought about it over the years and just thought all the time what will people think?" she told CY Interviews at the time of the issue's release. "I guess being at my age now it's sort of like I really wanted to do it for me, and it wasn't what other people thought."

Reflecting on her Playboy cover on an October 2020 episode of "The Real," she said, "Let me tell you, it was something that you have to muster — you know, you gotta be brave about it." She also shared that she got to call the shots on her shoot. "I got to pick my glam. I got to pick where we shot it. I got to pick what I was willing to show and not show."

Beauvais saw the experience as positive for a deeper reason, too. "It was a great thing because, first of all, not that many Black women are on the cover of Playboy — we can probably count them on one hand — so for me it was really an honor," she said. Would she do it again? "Once is enough," she said, before joking that she would "need a lot more airbrushing now." Hardly!

Denise Richards appeared on the cover of Playboy in December 2004, which, as Complex noted, was less than a year after she gave birth to daughter Sam Sheen. Richards and Charlie Sheen were married at the time of her Christmas shoot. In 2005, the couple went on to welcome daughter Lola Sheen. As her kids grew older, Richards felt it was important to explain her Playboy shoot to them. On a 2019 episode of the "Daddy Issues" podcast with Dean McDermott, Adam Hunter, and Nicky Paris, Richards said, "I'm honest with them" (via Us Weekly).

The "Starship Troopers" actor continued, "They had heard that I was in Playboy. I didn't even think that they would know what that is because now kids can go on the internet and see all kinds of things, so [I had] to explain that." But her daughters also avoid snooping and curiosity when it comes to Richards. "They don't Google [me]," she added. "I don't think they want to know certain things either. I wouldn't want to read certain things about my parents." It makes sense.

Richards has some nostalgia about her Playboy era. In July 2019, she shared a bikini-tastic throwback photo on Instagram to celebrate National Bikini Day. In the shot, she's wearing what looks like a swimsuit top fashioned out of palm fronds. "why not have one made out of leaves? #playboy," she wrote. Honestly, it's a great look.

When actor Robin Givens decided to be the Playboy cover girl on the September 1994 issue, it was for a very significant reason. As she shared on E!'s "Just the Sip" in November 2019, she was eager to get the chance to "write her own article." Alluding to her volatile marriage to Mike Tyson — which ended in abuse allegations — she said, "I felt like my own voice at the time had gotten so lost so I wanted to speak for myself. I think that was a time I had this fearlessness and I just believed in right and standing up and I believed in justice."

But years later, Givens has an even stronger hold on her own voice and future. She told E!, "I feel happy. I don't want to be afraid to be happy and branch out and spread my wings and fly and be all that I was intended to be. I don't want to be afraid of that. I really want to enjoy it." Not a bad mantra to live by.

Per Complex, even though Givens' Playboy cover came out five years after their marriage ended, it still featured a reference to the heavyweight boxer: "Robin Givens delivers a knockout pictorial." 

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Golden Globe winner and legendary sex symbol Raquel Welch appeared on the cover of Playboy in December 1979, wearing a red one-piece bathing suit. According to the Daily Mail, Hugh Hefner asked Welch "no less than 57 times" to grace the magazine. However, when she finally conceded, Welch refused to bare all for the camera. And apparently, this did not go over super well with Hefner. 

On "Life Stories" with Piers Morgan, Welch described the process of negotiating this deal with Hefner (via Independent.ie). "I got called into the front office to speak with Hugh in his bathrobe," Welch said. "I went over to the mansion and I brought my lawyer with me and I sat there in front of him and I said, 'What's the problem, Hugh?' and he said, 'Well there's no t*** and there's no a**.'" Welch pointed out that this had already been negotiated, but he replied, "Yes, but it's boring." Despite Hefner's disappointment, Welch still got paid.

So why didn't she want to pose totally naked? "I am my father's daughter and that's just not the way you behave," she told Morgan, noting taking it all off for the camera did not align with the values that'd been instilled in her. Well, she seemed to have her cake and eat it too with Playboy.

Heather Rae Young rose to fame on Netflix's "Selling Sunset," a reality show that follows Los Angeles realtors as they peddle multimillion dollar homes. In February 2010, when she was 23 years old, Young was a Playboy centerfold. "It catapulted my career, it changed my life, it was the most defining moment in my life," she said to The Sun. "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."

Young married HGTV star Tarek El Moussa in October 2021 and became a stepmom to his two children, Taylor and Brayden El Moussa, whom he shares with ex-wife, Christina Haack. "I'm still trying to figure out how I'm going to tell the kids I did Playboy," she shared with The Sun.

We have a feeling it'll go just fine. On Instagram in May 2021, Young spoke of the joy of being a stepmom. "Over the past couple of years of being a bonus mom, I've had the most special experience of being in Tay and Bray's lives, watching them grow up, putting them first, being there for them no matter what, and bonding with them on a whole new level," Young wrote (via People). "It's the biggest blessing in my life." Sounds like a lot of love and support going around.