It was Marilyn in 1953. And Bretman Rock in 2021. But amidst thousands of bunny ears and
tails, fans also ogled A-listers like Cindy, Denise, Lindsay and Madonna. Keep watching
for who put it all on the line.
"I only read the articles."
Supermodel Cindy Crawford was on the cover of Playboy in July 1988 and again that October.
She was shot by famed photographer Herb Ritts, and the collab was a brilliant one. According
to the Museum of Fine Arts Boston, Ritts was all about…
"Celebrating the human body and embracing the carefree California lifestyle."
As Vanity Fair noted, Ritts also introduced Crawford to her future hubby, actor Richard
Gere. Crawford and Gere were married in 1991 and divorced a few years later.
"Even then, even in the middle of it, you knew it was a pretty major moment."
Now that she's in her 50s, Crawford fondly remembers her sizzling modeling days. She
told Net-A-Porter in 2019,
"I look back at some of my old 'Playboy' pictures and I think, 'Why wasn't I walking around
naked all the time?'"
For the record, she's still a total knockout.
Lindsay Lohan was on the cover of Playboy for the January/February issue in 2012. And
her appearance came at a contentious time in her life. Just before her debut with the
brand, Reuters reported that the star was arrested in 2011 on charges related to drunk
driving, which violated her probation.
"I learn from my mistakes and I think that's the most important thing."
But nevermind the legal issues! At the time, a spokesperson for Lohan claimed of her spread,
"The pictorial is absolutely fantastic and very tasteful, and will be accompanied by
an interview that will let readers see another side of Lindsay."
But Playboy had to shell out some serious cash to land Lohan. According to TMZ, she
was originally offered $750,000 and came back with a demand of $1 million. Evidently, LiLo
accepted a counteroffer. As MTV News reported at the time, photos of the highly anticipated
shoot were leaked early. And in an effort to spin the situation into gold, Hef tweeted:
"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."
Drew Barrymore was splashed all over the January issue in 1995, when she was just 19 years
old. But while she saw it as empowering, Steven Spielberg — who famously directed Barrymore
in "E.T." when she was 7 — was less than impressed. Barrymore explained to the Hollywood
Foreign Press at the time,
"He still sees me as a child, makes me remove my lipstick when I go into his office. Wait
till he sees me nude in 'Playboy.' His scolding phone call!"
But even so, Barrymore had nothing but good things to say about her shoot. She added,
"It was like my own personal adventure. 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.
I'm not for extra gratuitous nudity but this was really interesting and a dare."
Spielberg's reaction went a bit beyond a phone call — but it was all in good fun. As the
pair recounted on "The Drew Barrymore Show" in 2021, the director gifted her with a quilt
that read "Cover Up" and used paper doll outfits to dress her photos. And in response, Barrymore
sent him a series of shots of herself in a nun's habit with captions that read:
"I'm sorry."
"I've seen the light."
"I'm on my way."
"And those are still, like, in one of your rooms in your house. Yes! Oh my God, there
it is!"
Fashion icon Naomi Campbell landed on the cover of Playboy in '99. But she was already
a shining star by then. As Vogue France noted,
"She became a cult figure of the 1990s with her feline gaze, dynamic personality and biting
comebacks [and] has dominated the fashion scene ever since."
The year after the issue hit the newsstands, Campbell explained to ABC News,
"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."
But it wasn't the last time she went topless. As the Daily Mail reported, she posed shirt-free
for Interview magazine in 2012, and for NARS Cosmetics in 2019.
Ex-wife of Rolling Stones frontman Mick Jagger, Jerry Hall, and their daughter Lizzy Jagger,
have both posed for Playboy.
Hall was in the October 1985 issue after staying pretty buttoned-up throughout her career.
She told The Daily Telegraph that when she was 16, artist Salvador Dali had offered her
a part in a movie. But she turned it down, saying,
"At that point I wasn't doing nude — my mum didn't want me to do nude — so I said
no. But I really regret that. That would have been faaabulous."
Years later, daughter Lizzy covered the June 2011 issue, dishing on fans' misconceptions
of her. As she told the magazine,
"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. But I do like to have a bit of fun.
[…] And at 27, I feel comfortable expressing myself through my body."
As the Material Girl herself tells it, Madonna worked as a nude model for art and photography
classes when she was 19, and living in New York City. Explaining that she just did it
to pay the bills, she also revealed on Instagram,
"Many of these photos were sold to 'Playboy' and 'Penthouse' when I became famous. The
Photographer’s Exploited Me and then the Patriarchy tried to Shame me for Being Naked."
"I think we got this shot."
As Complex recounted, Playboy released the shots in the September 1985 issue. And Madge
was still game to do the cover — but fully clothed. Still, the photos and her unapologetic
response to any shaming eventually led to a collab with artists Keith Haring and Andy
Warhol. As Madonna noted in her post,
"You cannot stop Art by trying to Shame it. Creation always wins."
When actor Olivia Munn shot the July/August 2009 issue, she negotiated a PG cover. But
even so, wardrobe issues ensued. In her memoir, "Suck it, Wonder Woman," Munn claimed she
requested her own stylist for the shoot, but the photographer had a different plan. She
recalled,
"I get a call saying that this photographer insists on using a different wardrobe stylist.
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."
When Munn ultimately met the other wardrobe person, she didn't like the options, including,
as she noted…
"A black, fishnet one-piece bathing suit where you can see everything going on."
"Lounging and trying to look awesome while I'm, you know, kind of exposed isn't the most
comfortable for me."
After a lot of back and forth, Munn ultimately got the more modest shoot that she was originally
promised. As she explained to Kotaku.com,
"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. There's nothing
wrong with it, it's just not something I'd do."
Model and burlesque dancer Dita Von Teese covered the December issue in 2002. But as
the story goes, the star's full stage name actually came about thanks to the magazine.
As she told Vogue, she was born Heather Sweet, but had gone by "Dita" for years. And when
she posed for Playboy in the '90s, they asked for her last name. With a phone book in hand
to source some ideas, she said,
"I found the name Von Treese and I called 'Playboy' and said, 'I'm going to be Dita
Von Treese.'"
"You can be whatever character you want, with lingerie, too."
But the mag accidentally called her "Teese" — and the rest is history. The model added,
"I had a laugh once when somebody once said, 'Oh, her name is so fabricated.' And I'm like,
'It's a typo!'"
Back in the 90s, a then up-and-coming Sharon Stone hoped Playboy would help her land the
role of a lifetime. And it definitely did. Claiming she's all about making those business
moves, she told "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."
A few years later, she revealed just how 'Basic Instinct' changed everything for her, explaining
to Playboy,
"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. […] Sudden
fame of this enormity is scary."
But after that bumpy start, Stone has been riding the wave ever since. In 2014, when
Oprah asked about the "pressure" that comes with being a lifelong bombshell, Stone replied,
"It's a pleasure for me now. I mean, I'm going to be 56 years old, if people want to think
I'm a sex symbol, it's like, yeah!"
Actor and "Real Housewives of Beverly Hills" star Garcelle Beauvais landed the August 2007
cover at 40 years old. And as she told C Y Interview at the time,
"I thought about it over the years and just thought all the time what will people think?
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 covergirl status with the brand, the star revealed that she chose her
own glam squad, the location, and how far she wanted to go. As she shared on "The Real,"
"Let me tell you, it was something that you have to muster your — you know, you gotta
be brave about it."
Still, she says one time was plenty when it comes to doing a shoot like that. She added,
"Mmm…I don't think I need to do it again. I think once is enough."
Denise Richards covered Playboy in December 2004 — less than a year after she gave birth
to her daughter Sam. Richards was married to Charlie Sheen at the time, later welcoming
daughters Lola and Eloise. But as her kids grew older, Richards wanted to be open about
her history with the iconic brand.
"I feel great walking down the beach in my bikini."
She revealed on the "Daddy Issues" podcast in 2019,
"I'm honest with them. They had heard that I was in 'Playboy.' I didn't even think that
they would know what that is."
But she also thinks her kids might not want to know the whole story either. Because kids
are always grossed out by their parents, no matter what, forever.
Actor Robin Givens covered the September '94 issue for a very significant reason. She wanted
to share her own perspective on her volatile marriage to boxer Mike Tyson. As she recalled
on "Just the Sip,"
"I felt like my own voice at the time had gotten so lost so I wanted to speak, myself."
Describing how she loves writing and even penned her own article to accompany her spread
in the magazine, she added,
"I just kind of believed in right, and I believed in standing up, and I kind of believed in
justice."
And these days, it appears that Givens is truly living her life to the fullest. As she
explained,
"I feel happy. I don't want to be afraid to be happy and branch out and spread my wings
and fly."
Iconic sex symbol Raquel Welch was on the cover of Playboy back in December 1979. And,
according to the Daily Mail, Hef had asked her "no less than 57 times" to shoot the cover.
But the model refused to bare it all. And that didn't go over well with Hef.
As the star recalled on "Life Stories," she had negotiated a more modest shoot, but was
eventually called in to Hef's office to hash things out with him — with her lawyer close by.
"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 ass.'"
Despite the awkward situation, Welch still walked away with her hard-earned paycheck.
Heather Rae Young rose to fame on "Selling Sunset." But back in 2010, she was a 23-year-old
Playboy centerfold. As she told 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."
Young went on to marry HGTV star Tarek El Moussa in October 2021 and became a stepmom
to his two kids. But as she revealed to Access,
"I'm still trying to figure out how I'm going to tell the kids I did 'Playboy.'"
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