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The Most Famous Women of Playboy

Vanna White

Vanna White

Of all the people we thought we'd see in the pages of Playboy, we never imagined we'd find Vanna White there! The Wheel of Fortune superstar is definitely beautiful enough to appear on the cover (even to this day), but people were shocked when they saw how much she revealed in her 1980s photoshoot. 

Even White herself had regrets about the scandalous photos. While reflecting on the controversy, White says she remembers, "going on ‘Johnny Carson’ and saying, ‘I’m so sorry … I made a mistake, I’m sorry and I just hope I don’t lose my job over it.’" Thankfully, she's still on Wheel of Fortune turning letters! 

(Image via Playboy Enterprises)

Farrah Fawcett

Farrah Fawcett

Farrah Fawcett had a lot going on in her impressive career, but the Charlie's Angels actress still managed to find time to pose for Playboy multiple times during her life! Her first appearance was in 1978, where she appeared scantily clad on the cover, but at the time, she refused to go fully nude. 

However, that all changed by the time 1995 rolled around. That was the year she really caused a stir by appearing nude in the magazine for the first time. However, it wouldn't be her last. She appeared again in 1997 where she introduced the world to her strange art style of painting with her nude body. 

(Image via Playboy Enterprises)

Kate Moss

Kate Moss

Many people would want to appear on Playboy when they are young and in their prime. However, model Kate Moss proved that age is just a number when she made an appearance in the magazine when she was almost 40 years old. And honestly, she looked great no matter what age she was. 

The cover of her issue, which was released for the magazine's 60th anniversary, saw her clad as an iconic Playboy bunny. However, within the pages of the magazine, her photos took a much more risque turn. Kate Moss has clearly still got it going on! 

(Image via Playboy Enterprises)

Tara Reid

Tara Reid

Aside from a few Sharknado appearances, the world hasn't heard from Tara Reid in years. Reid was once an in-demand actress, starring in low-brow comedies like the American Pie series. So, it was a shock to us all when Reid appeared on the cover of the January 2010 issue of Playboy

However, it wasn't just a photoshoot for Reid--she had something to prove to the public. In the years leading up to her cover, Reid had undergone several botched plastic surgery procedures. She wanted the world to see that she had "fixed" her body, and, in her defense, that's exactly what she proved. 

(Image via Playboy Enterprises)

Olivia Munn

Olivia Munn

It was a challenge to get actress Olivia Munn on the cover of Playboy, but, somehow, the brains at the magazine managed to make it happen. While she was initially reluctant to appear on the cover, she eventually decided it was worth a go--as long as she didn't have to pose nude. 

Munn talked about her experience posing for Playboy in her memoir, Suck It, Wonder Woman! She describes drawn-out negotiations with the magazine about what exactly she would show in her photos, and she also discusses them trying to convince her to bare it all. 

(Image via Playboy Enterprises)

Carmen Electra

Carmen Electra

For most celebrities, posing for Playboy once is enough. However, that wasn't the case for Carmen Electra! The model and actress has posed five times for the magazine, and we're sure that fans aren't mad about it. Her first appearance came in 1996, and her most recent was for Playboy's 55th anniversary. 

While she had some misgivings at first, Electra says her time with Playboy was positive--"I realized that Playboy was very … They were very respectful. There weren’t people hanging around on set. The lighting was amazing. The photographers were very friendly and aware that you’re a woman and you’re posing nude, and so it did make it easier."

(Image via Playboy Enterprises)

Jenny McCarthy

Jenny McCarthy

Jenny McCarthy made a full-blown career out of her time at Playboy. Unlike some who appeared on the cover, McCarthy went all in on the scantily clad life and managed to make a name for herself out of it. And, unlike cover stars, McCarthy was an unknown the first time she posed. 

Her first appearance for Playboy was in 1993 after catching Hugh Hefner's eye. She would go on to win Playmate of the Year for her work. However, the appearance caused a stir back in her hometown, with her family's home being hit with eggs and her relatives harassed. 

(Image via Playboy Enterprises)

Sharon Stone

Sharon Stone

Sharon Stone is probably most famous for the scene in Basic Instinct where she shows it all to the world with a well-timed leg cross. However, that iconic scene probably would never have happened if it weren't for a little help from Playboy. Stone credits her appearance in the magazine as helping her land that role. 

Stone revealed this in 2020 on The Drew Barrymore Show where she described herself as "more of a logic and strategy person," before detailing her plan to get into Playboy in order to help improve her chances of landing the Basic Instinct role. This is one woman who knows what she wants! 

(Image via Playboy Enterprises)

Naomi Campbell

Naomi Campbell

As one of the world's most famous supermodels, it's no surprise that Namoi Campbell was down to pose for Playboy. She's a woman who knows just how good she looks, and she's not afraid to show it off to the world. However, some fans were shocked at just how much skin she managed to bare for the magazine. 

Campbell appeared in the 1999 holiday issue of the magazine, so it's no surprise she went with a winter white theme. However, she's not so much wearing an actual outfit as she is wearing strips of white fabric wrapped strategically around her body. A very merry Christmas to us all! 

(Image via Playboy Enterprises)

Raquel Welch

Raquel Welch

"Always leave them wanting more," is a great philosophy for all aspects of life, and that's something that actress Raquel Welch knew to be true. She may have appeared on the cover of Playboy in 1979, but she held firm about not posing nude. But this didn't anger Hugh Hefner, in fact, he said it just made her that much sexier. 

He said this about her famous shoot--"Raquel Welch, one of the last of the classic sex symbols, came from the era when you could be considered the sexiest woman in the world without taking your clothes off. She declined to do complete nudity, and I yielded gracefully. The pictures prove her point."

(Image via Playboy Enterprises)

Bo Derek

Bo Derek

At the beginning of the 1980s, the world was in love with Bo Derek thanks to her role in the wildly successful movie 10. Overnight, Derek became a sex symbol (along with her iconic cornrows she sported in the movie), so it was only a matter of time before she made her way into the pages of Playboy

That moment finally came when she appeared in the March 1980 issue of Playboy. Derek was sans cornrows (and sans pretty much everything else), but she still managed to look amazing. Over the years, it's become one of the most iconic covers of all time. 

(Image via Playboy Enterprises)

Cindy Crawford

Cindy Crawford

Supermodel Cindy Crawford has appeared for Playboy not once but twice! Her first nude photoshoot appeared in the magazine's July 1988 issue, and another one was featured a decade later in October of 1998. Unsurprisingly, she looked amazing both times! 

Crawford has no regrets about baring it all for the magazine, and she doesn't particularly care if people disagree with her decisions. She told Playboy, "People have to compartmentalize me. They can't deal with a woman who has a serious career taking off her clothes and being sexy."

(Image via Playboy Enterprises)

Shannen Doherty

Shannen Doherty

Shannen Doherty is another star who has had multiple appearances in the pages of Playboy. Her first spread came in March of 1994, with her second appearance coming in December of 2003. However, she didn't just show a little skin, she also opened up about her sometimes controversial life. 

"I wish I had conducted myself better on occasion and been more private, but I would rather live my life to the fullest than constantly conduct myself in a certain way to gain approval from others. I've always been outspoken about my opinions, and there's something to be said for having the courage to just live your life. I have regrets but no apologies."

(Image via Playboy Enterprises)

Elle MacPherson

Elle MacPherson

Elle MacPherson is clearly an expert when it comes to magazine covers. The Australian model is most famous for her multiple appearances on the cover of Sports Illustrated's swimsuit issues--which led to her nickname, "The Body." But it goes without saying that she showed much more body in her Playboy appearance! 

MacPherson decided she needed to pose for the magazine in 1994 when she learned that media types had been searching for nude photos of her. Her rationale was that if there were going to be nude photos of her circulating, she was going to do them on her own terms. And she did just that! 

(Image via Playboy Enterprises)

Brooke Shields

Brooke Shields

Brooke Shields' appearances in Playboy and related publications have been a source of controversy for years. Jaws dropped when it was revealed that nude photos of a ten-year-old Shields appeared in a Playboy offshoot publication (with the blessing of her mother, no less) in the 1970s. 

That wasn't Shields' only work for Playboy, though. She appeared in the magazine proper in their December 1986 issue. The original photos of a young Shields obviously caused major controversy, including in 2009 when an artist attempted to include the pictures in a work and was told he could face obscenity charges. 

(Image via Playboy Enterprises)

Lisa Rinna

Lisa Rinna

Lisa Rinna is soap opera (and reality television) royalty, and she even has a few appearances for Playboy under her belt, too! Rinna appeared in the magazine in 2009, but it was her 1998 appearance that really turned heads. Playboy may not be a family magazine, but Rinna was definitely in the family way when she was photographed. 

In 1998, Rinna did a nude, 10-page spread for the magazine--all while she was six months pregnant! It was a boundary-pushing shoot, but this is one lady who is no stranger to controversy. However, we imagine her kids will be mortified if they ever find out that they technically appeared in Playboy too. 

(Image via Playboy Enterprises)

Jaime Pressly

Jaime Pressly

Jaime Pressly is no stranger to men's magazines. She's done them all, including Maxim and, of course, Playboy. And judging from her photoshoot with the magazine, it's clear she has no problem showing a little skin...and then some. Her appearance came in the February 2004 issue. 

As you might imagine, working for Playboy can be a risky career move. It might open some doors, but it can close others. Pressly dropped this hilarious gem in the middle of an unrelated interview, and it's good advice to keep in mind--"Once you've appeared in Playboy, you can't ever work for Procter & Gamble." 

(Image via Playboy Enterprises)

Anna Faris

Anna Faris

While it may not be her best work, Anna Faris' first big claim to fame was her starring role in the 2008 comedy The House Bunny where she plays a former Playboy bunny working as a sorority house mother. It seems painfully obvious that Playboy would want her on the cover, and they managed to get their way!

While hers was not the most risque appearance of all time (she did not appear nude), she looked great in the pages of the magazine. Despite being self-conscious about her body in high school, it's clear the actress had a change of heart before her time in Playboy!

(Image via Playboy Enterprises)

Jessica Alba

Jessica Alba

Jessica Alba is another actress to have appeared on the cover of Playboy more than once. However, one of these covers was met with controversy.

Alba first appeared on the cover of Japanese Playboy without any issue. Things changed when she appeared on the American cover in 2006. Alba sued with claims that her photo was used without her permission, but she later would drop the lawsuit. 

(Image via Playboy Enterprises)

Bridget Marquardt

Bridget Marquardt

Like Holly Madison, Bridget Marquardt was one of three Playboy bunnies to date Hugh Hefner in the 2000s. She was also featured on The Girls Next Door, where her life as Hefner’s girlfriend was documented. 

While Marquardt has had some acting work since her time at the Playboy mansion, most of her credits come from shows where she appears as herself. 

(Image via Playboy Enterprises)

Marilyn Monroe

Marilyn Monroe

Marilyn Monroe on the cover of Playboy would be historical enough. But this iconic Hollywood star took things a step further. 

Monroe was featured on the very first issue of Playboy magazine--which was published all the way back in December of 1953. 

(Image via Playboy Enterprises)

Lindsay Lohan

Lindsay Lohan

Say what you will about Lindsay Lohan--her Playboy cover is one of the most memorable ones out there. She appeared on the January/February 2012 issue. 

Not willing to be encumbered by clothing, the infamous starlet decided to just use a bunny-shaped chair to cover up her most important bits. What else would you expect from Lohan? 

(Image via Playboy Enterprises)

Barbi Benton

Barbi Benton

Barbi Benton is an American actress who is best known for her roles in TV shows like Hee Haw and The Love Boat. However, before all that, she rose through the ranks of Playboy. 

Benton originally appeared as an extra on the TV show Playboy After Dark, but she was quickly promoted to co-host after catching Hugh Hefner’s eye. The two dated for several years, and Benton was even the one who convinced Hefner to buy the Playboy mansion. 

(Image via Playboy Enterprises)

Kim Kardashian

Kim Kardashian

Kim Kardashian appeared on Playboy all the way back in December of 2007. Has she really been famous that long? 

In true Kardashian style, the whole cover was a tie-in. The photoshoot was well documented in season 1 of her reality show, Keeping Up with the Kardashians. 

(Image via Playboy Enterprises)

Dolly Parton

Dolly Parton

Dolly Parton was an old pro in the music world by 1978. That was the year she released her TWENTIETH studio album. So, she decided to try her hand at something else. 

That something else just happened to be the cover of Playboy. Southern belle, Playboy bunny--Dolly can do it all! 

(Image via Playboy Enterprises)

Joan Collins

Joan Collins

Joan Collins is probably most famous for her role as Alexis Colby on the '80s hit, Dynasty. However, she’s had an acting career that stretches all the way back to 1955!

It should come as no surprise that the beautiful Collins appeared on the cover of Playboy at the height of her Dynasty fame. Her issue came out in December of 1983. 

(Image via Playboy Enterprises)

Suzanne Somers

Suzanne Somers

Three may be company, but one Playboy cover was just not enough for actress Suzanne Somers. So, she made two appearances!

Her first appearance was on the cover of the French version of Playboy, but she eventually made her American debut in December of 1984. 

(Image via Playboy Enterprises)

Bonnie Halpin

Bonnie Halpin

Bonnie Halpin made Playboy history as the first “door bunny” (aka a greeter) on the opening day of the first Playboy Club back in 1960. Her daring personality and gorgeous figure quickly made her a favorite around the club. 

She would go on to spend three years working for Playboy in various roles. These roles included posing for advertisements and making it onto the October 1962 cover of the magazine. 

(Image via Playboy Enterprises)

Mariah Carey

Mariah Carey

All I want for Christmas is that one-piece Mariah Carey wore on her cover of Playboy. The singer and (sorta) actress was just one in a long line of beautiful and famous women to grace the cover of the magazine. 

Carey appeared on the March 2007 cover. She wasn’t completely nude--but not for lack of trying! 

(Image via Playboy Enterprises)

Paris Hilton

Paris Hilton

Paris Hilton definitely did not need Playboy to help increase her notoriety (or infamy). That being said, it should come as no surprise that the hotel heiress and entrepreneur made an appearance. 

Hilton appeared on the March 2005 cover, all decked out in red. It seems more appropriate for December or February, but I’m sure that Playboy patrons were not complaining. 

(Image via Playboy Enterprises)

Goldie Hawn

Goldie Hawn

Goldie Hawn has had plenty of hilarious roles over the course of her career. So, it should come as no surprise that she got a little funny with her Playboy cover. 

Hawn appeared on the January 1985 cover of the magazine. And while she looks great, fishnet stockings inside a giant champagne glass is definitely not the most serious, sensual look. 

(Image via Playboy Enterprises)

Denise Richards

Denise Richards

People have had their eye on Denise Richards ever since her breakthrough role in 1997’s Starship Troopers. She appeared on the cover of Playboy in the mid-2000s at the height of her acting career. 

Richards appeared on the December 2004 issue, and it shows. She’s all decked out like a scantily clad Christmas tree. 

(Image via Playboy Enterprises)

Madonna

Madonna

The Material Girl herself has even appeared on the cover of Playboy! She might have spent most of the '80s making hit music, but Madonna managed to find time for the historic magazine. 

She appeared on the cover of the September 1985 issue. Additionally, she appeared much less clothed within the pages of this particular issue. 

(Image via Playboy Enterprises)

Barbra Streisand

Barbra Streisand

Barbra Streisand was hot off her second Oscar win when she posed for the cover of the magazine. In case you’ve forgotten, she looks just as good as she sounds.

Streisand appeared on the October 1977 cover. And in true Streisand style, her photo was captioned with, “What’s a nice Jewish girl like me doing on the cover of Playboy?”

(Image via Playboy Enterprises)

Drew Barrymore

Drew Barrymore

People couldn’t get enough of Drew Barrymore in the '90s--including Playboy. The actress appeared on the cover of the magazine just a year before her iconic role in 1996’s Scream

Barrymore’s issue dropped in January of 1995, and, when compared to some celebrities that have graced the cover, she’s baring quite a bit of skin. 

(Image via Playboy Enterprises)

Kendra Wilkinson

Kendra Wilkinson

Kendra Wilkinson may have dated Hugh Hefner in the early 2000s, but she’s managed to make a full-blown career out of it. She rose to fame initially when she appeared on the Playboy-themed reality show, The Girls Next Door. 

Since her time dating Hefner, Wilkinson has been able to leverage her fame to obtain even more opportunities. These include her own spin-off from The Girls Next Door, as well as numerous appearances on other reality shows. 

(Image via Playboy Enterprises)

Dorothy Stratten

Dorothy Stratten

Dorothy Stratten was a model and actress who was named Playmate of the Year 1980. Unfortunately, Stratten is more famous for her murder than her work. 

Stratten was murdered at age 20 by her estranged husband, Paul Snider, who had recently learned of Stratten’s affair with director Peter Bogdanovich. 

(Image via Playboy Enterprises)

Crystal Hefner

Crystal Hefner

Crystal Hefner appeared in the pages of Playboy a few years before she would become Hugh Hefner’s third wife. She was the last woman married to Hefner before his death in 2017. 

They worked things out, but the relationship between the two did not start off great. The two were originally supposed to be married in 2011, but Crystal called off the wedding five days before it took place. They finally worked things out and married in 2012. 

(Image via Playboy Enterprises)