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. She looks truly stunning on the cover, but the inside really didn't leave much left the imagination.
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!
As a result of her appearance on the cover, Vanna White filed a lawsuit, saying she the pictures were taken by photographer David Gurian in 1982, and not for Playboy initially. But Hefner purchased the photos and used them for his magazine.
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. After the 2000s, Tara Reid's career really took a dive. So, it was a shock to us all when Reid appeared on the cover of the January 2010 issue of Playboy. The results were pretty...impressive.
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. She looked great on the cover but really, she had nothing to prove.
Tricia Helfer had Sci Fi geeks everywhere lusting after the Cylon Model Number 6. Her out of this world body and sexy smirk drove us all wild for years! It’s no surprise she found herself on the cover of Playboy. It was only a matter of time! This revealing cover showed a whole lot more of Helfer than Battlestar Galactica fans were certainly used to seeing.
Most recently, you could find her on the hit Netflix series Lucifer as Charlotte Richards, but she actually got her start as a model and won the Ford Model’s Supermodel of the World contest. Her cover pic for Playboy gives us a naughty glance; maybe that’s what snagged her the title for Ford. In addition to film and television roles, she's also done some video game voice work.
Farrah Fawcett had a lot going on in her impressive television and modeling 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, she didn't stick to that decision for long.
That all changed by the time the year 1995 rolled around. That was the year she really caused a stir by appearing nude in the magazine for the first time. Her male fans were pleased as she finally did what she said she would never do. However, it wouldn't be her last appearance. She appeared again in 1997 when she introduced the world to her strange art style of painting with her nude body.
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 has looked great no matter what age she was. Kate Moss looked absolutely breathtaking on this photo much to the enjoyment of her fans.
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!
That Playboy cover would be the last printed Playboy anniversary cover in existence, at least so far, as the magazine is no longer in print.
For most celebrities, posing for Playboy once is enough. However, that wasn't the case for Carmen Electra! As one of the hugest sex symbols of the '90s, this was definitely someone people wanted to see on the cover. 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." Carmen Electra may not be in the public eye as much as before but we always have these covers to remember her by.
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. And as you can see on this cover she is not nude. She's just wearing a swimsuit.
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.
Munn wrote in her book, Suck It, Wonder Woman, “Getting the cover, and not having to be nude, was a huge deal to me and my team," adding "Only a handful of people have done it without having to take it all off. And here we are, contracts decided, conversations spanning weeks about this day, and everyone has a different agenda.”
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. Jenny McCarthy became even bigger because she had both looks and charm - and she was pretty funny too.
Her first appearance for Playboy was in 1993 after catching Hugh Hefner's eye for her "wholesome catholic girl" look. For that shoot, she was offered $20,000. 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.
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 as one of the most famous scenes in the movie involves her revealing quite a bit as she uncrosses her legs.
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! The actress ended up earning an Academy Award nomination and in 1995 she earned a star on the Hollywood Walk of Fame.
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. The English model, actress and singer had been modeling since she was 15 years old and achieved international success by the late '80s.
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! And this was all after Time had declared the era of the supermodel to be dead, which, clearly, they were wrong.
"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. The American actress became a sex symbol of '60s and '70s, but she always stayed true to who she was.
Hugh Hefner 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."
And in Welch's words, "I was not brought up to be a sex symbol, nor is it in my nature to be one. The fact that I became one is probably the loveliest, most glamorous and fortunate misunderstanding."
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), later appearing in films such as Fantasies, Tarzan, The Ape Man, and Ghosts Can't Do It, 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. Fans of Derek will never forget.
She continues her film career to this very day, although the roles certainly aren't as big. She also tends to her horses and is a huge activist for the humane treatment of horses.
Supermodel Cindy Crawford was a huge name throughout the '90s and had that signature mole that only she could pull off. 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 for the magazine!
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, "That provoked me and made me want to push their buttons a little. People have to compartmentalize me. They can't deal with a woman who has a serious career taking off her clothes and being sexy."
Kim Kardashian appeared on Playboy all the way back in December of 2007. Has she really been famous that long? Famous for being famous, Kardashian was born into a wealthy family and had a hot mom, so it's no surprise she turned out to be quite a beauty herself. But she also became famous for a scandalous sex tape that really launched her career.
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. And she certainly had no regrets.
Taking a trip down memory lane, she resurfaced the photos on her Instagram account, with a caption saying, "I found these old photos from my December 2007 Playboy Magazine shoot by Hype Williams and had to post them!" She adds, "They are so good. Awww, I look like a baby LOL!"
Shannen Doherty is another star who has had multiple appearances in the pages of Playboy. Famous for her stint on the series Beverly Hills, 90210 , she became a household name in the '90s. 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."
In 2020, Doherty announced that she had stage four cancer and would be undergoing treatment. In 2021, she gave an update on her treatment, showing she's still got plenty of fight in her.
Brooke Shields was a child model who would eventually get into film, starring in Blue Lagoon and Endless Love. 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 properly in their December 1986 issue, which was a lot less creepy and gross not that she was an adult doing it. 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.
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! Not that anyone was complaining about that, however.
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! In 2013, she recreated her famous cover for the Australian magazine, Harper's Bazaar.
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. A shoot that she would reshare for her 57th birthday on her Instagram account.
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, as she posted nude with her naked baby in the photo as well.
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. So, in addition to being a singer, actress, radio host and director, you can also add the feat of being a Playboy model as well.
Carey appeared on the March 2007 cover. She wasn’t completely nude--but not for lack of trying! Apparently, while she wanted to appear nude in the magazine, the magazine wanted to cut costs and not airbrush an entire nude photo as rumor has it. Did they ever consider not airbrushing? Hmmm. Nevertheless, Mariah Carey made quite an impression.
Jaime Pressly is no stranger to men's magazines. She's done them all, including Maxim, STUFF 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. It would be the only time that Pressly would appear on the cover.
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."
Most recently, Pressly appeared in the television series Welcome to Flatch as a recurring character in the show's second season.
Anna Faris has had both the beauty and the sense of humor to really make her a star. 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. She wasn't always so confident, however, in her words saying, "I wore glasses, braces, odd hairdos and dumpy clothes. I was clumsy and awkward. When I was a freshman I wore a Christmas tree skirt as a cape. I couldn’t get any dates until senior year.” But 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! And the actress still looks great to this very day.
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. But then she was featured on the magazine in 2006, only she didn't know she would be featured on the magazine.
Alba was featured on the cover of Playboy's "25 Sexiest Celebrities" in 2006 without her knowledge. Alba sued with claims that her photo was used without her permission, but she later would drop the lawsuit. The image used was a promotional shot for her film Into the Blue and she felt that the headline implied that she would appear nude in the magazine. She dropped the lawsuit after receiving an apology from Hugh Hefner.
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. Interestingly, she was never considered an official Playboy Playmate but had appeared in nude pictorials with her Girls Next Door co-stars.
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. She can next be seen in the docu-series Secrets of Playboy. Is it going to be a hit piece? Probably, and we are here for every minute of it.
Marilyn Monroe was basically America's first sex symbol, although it was never something that she actually wanted. She is quoted as saying, "Being a sex symbol is a heavy load to carry, especially when one is tired, hurt and bewildered." But she also expressed that it could be worse, saying "That's the trouble, a sex symbol becomes a thing. But if I'm going to be a symbol of something, I'd rather have it sex than some other things we've got symbols of."
Marilyn Monroe on the cover of Playboy would be historical enough. But things escalated for this iconic Hollywood star when Monroe was featured on the very first issue of Playboy magazine--which was published all the way back in December of 1953. The problem was that she never actually posed for the magazine. The photos were published without her consent, and she was never paid for them.
Lindsay Lohan started out as a child star and as she grew into adulthood she became one of the hottest celebrities in more ways than one. Unfortunately, a number of controversies really wrecked her career. 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? However, uncensored versions of the photos were leaked online, so that's out there if you should feel so inclined.
We can’t talk Playboy without talking about Pamela Anderson’s “girl next door” flavor. It’s almost like this blonde bombshell was made for posing for Playboy. She drove all the boys, and probably some girls too, wild in the ‘90s and 2000s. Her smoldering eyes and naughty pose made this a cover to remember. She was one of the hottest stars in the '90s and things got even bigger when he sex tape with Tommy Lee leaked.
Pamela is so Playboy that she holds the record for most appearances in the magazine. She’s quite literally the original Baywatch babe, and she’s probably one of the most famous playmates of all time. Everyone wants a few minutes with Pamela…
However, since 2016, Pamela Anderson has been outspoken against the adult film industry, calling for the industry to gravitate more toward eroticism rather the meaningless objectification that goes on in the industry now.
Barbi Benton is an American actress who is best known for her roles in TV shows like Hee Haw and The Love Boat. On top of that, she was also a moderately successful singer in the '70s with hits like "Brass Buckles" in the Billboard top five country hits. 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.
After Hugh Hefner's death, Benton told People, "I cried all night [when I found out]. I was a basket case."
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. She had only appeared in a few films, including Americathon, Skatetown, USA, Autumn Born and Galaxina before she was killed. Her last film, They All Laughed, was released posthumously.
Stratten was murdered at age 20 by her estranged husband, Paul Snider, who had recently learned of Stratten’s affair with director Peter Bogdanovich. It was during the filming of They All Laughed that the affair began. Snider had purchased a 12-gauge he found an ad for in a local newspaper. Stratten had met with Snider under the assumption that they would be discussing a separation settlement, but that was not the case.
The hugely successful singer-songwriter Dolly Parton has had 25 number one hits on the Billboard country charts and has garnered 11 grammy awards. And over the last 40 years of her career as a singer and an actress, she's cemented a place in history. She's already been inducted in the Country Music Hall of Fame, as of 1999, and in 2022, the Rock and Roll Hall of Fame announced she would be inducted there as well.
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!
In honor of her husband's birthday, Parton recreated her special cover, wearing the same attire, in 2021.
Crystal Hefner appeared in the pages of Playboy a few years before she would become Hugh Hefner’s third wife. Named Playboy Playmate of the Month for December 2009, Crystal Harris (at the time) was the daughter of singer-songwriter Ray Harris. She's also college educated, having majored in psychology at San Diego State University.
Crystal became 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.
She still goes by the name Hefner and has an Instagram account with over 3 million followers.
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! The English actress has 136 credits to her name on IMDB and that's pretty impressive. She's earned a Primetime Emmy award and two Soap Opera Digest Awards. So its really no surprise Playboy wanted the beautiful actress on their cover.
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.
About the cover, Collins said, "When I was 49, I posed for Playboy - I was very flattered to be asked. I was quite honoured, really, considering that most of the models they feature are in their twenties."
Paris Hilton definitely did not need Playboy to help increase her notoriety (or infamy). She had already been in the media in the late '90s over various exploits due to her part-going ways but things really escalated when a sex tape with her then-boyfriend Rick Salomon released in 2003 - coincidentally, timed before the premiere of her reality series The Simple Life.
That being said, it should come as no surprise that the hotel heiress and entrepreneur made an appearance on the cover of Playboy. 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. On the cover, she was labeled "Sex Star of the Year."
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. Known for her character Chrissy Snow on Three's Company, both appearances were considerably memorable.
When talking to Access about the possibility of being featured on the Playboy cover again, Somers said, "Maybe on my 75th birthday....Actually, that would be really cool. I would like Annie Leibovitz to shoot me nude for Playboy for my 75th birthday."
Of course, that didn't end up happening as she is well past her 75th birthday.
Goldie Hawn has had plenty of hilarious roles over the course of her career. Some of her classic films have included Private Benjamin, Overboard, The Sugarland Express, Death Becomes Her and The First Wives Club. And the comedy legend is still working today, most recently in films like Snatched and The Christmas Chronicles. 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. Nevertheless, sometimes funny can be a whole lot sexier and that's exactly what Hawn achieved. It should be noted that she's only on the cover as you see and there are no other photos inside. Sorry folks.
If you’re into a girl that isn’t afraid to get a little weird, Charlize Theron is just for you! She’s no stranger to sci-fi, and her groundbreaking roles even landed her an Oscar. However, even Oscar winners pose for Playboy. It’s almost like a right of passage, and why not give the people what they want? Charlize Theron did just that and her fans seemed to appreciate it.
Charlize is one of those girls that can turn into anyone. She’s been all kinds of girls for different roles, and that’s why she’s one of the most desirable actresses in Hollywood…not to mention she’s pretty easy on the eyes. In her cover-shot for Playboy, she’s posing topless and she can’t be tamed.
However, the cover is not something she's too proud of, as she's been spotted rejecting signings of the cover for fans.
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. According to Hefner, "She was a very special lady." 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. Halpin would appear on the cover of the October 1962 issue of the magazine wearing different attire than the iconic satin bunny suit. But she was shown in the magazine wearing an early version of the bunny suit, which was a strapless, one-piece bathing suit that included the iconic bunny ears and cottontail, as well as the white cuffs, collar and black bow tie.
People have had their eye on Denise Richards ever since her breakthrough role in 1997’s Starship Troopers. This breakthrough role led to her appearance as a Bond girl in The World is Not Enough as well as films like Drop dead Gorgeous and Scary Movie 3. Of course, naturally, the hot young star who ranked #9 in Maxim's 50 Sexiest Women, would also be featured in Playboy.
Richards appeared on the cover of Playboy in the mid-2000s at the height of her acting career. She appeared on the December 2004 issue, and it shows. She’s all decked out like a scantily clad Christmas tree. She posed for a nude pictorial just five months after she had given birth, and she looked absolutely fantastic.
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. And certainly nobody was complaining at the time.
And really, Madonna can do whatever she wants cause she's earned it. She's pushed musical boundaries, redefining pop music for generations to come. Having sold over 300 million records worldwide, she's the best-selling female recording artist of all time and is considered the most successful solo artist in history. Nobody really does anything like Madonna but they certainly try.
Bai Ling got her start in Chinese films, but after getting her feet wet in acting she made the big decision to come to America to make it big! And make it big, she did. Bai Ling even made People Magazine's "50 Most Beautiful" list. She was in several major movies and won the attention of the New York Times…as well as the Chinese government…for her role in Red Corner.
Her Chinese citizenship was revoked because of the criticisms her portrayal in Red Corner made against human rights conditions in China. It really tarnished her career, leading to terminated movie contracts. However, we bet they were begging her to come back after her jaw-dropping 2005 Playboy cover. We know we would be!
In recent years, she has been able to return to her native country to make movies there, and fortunately, there have been changes made in the country that have made it returning there a more pleasant experience.
Singer and actress Barbra Streisand has had a hugely successful career over the past six decades. She's one of the few people to have earned an Emmy, Grammy, Oscar, and Tony award. 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?” Getting her in the magazine was no easy effort, as it took a year for Lawrence Grobel to get an interview with her but after some convincing, it all worked out.
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.
This was surprising given the fact that her family name has such a huge legacy in Hollywood. The family of actors has included Lionel Barrymore, Ethel Barrymore, and John Barrymore. We imagine that the attitudes to being on Playboy would have been a lot different in their time but Drew out here just tryin' to do her own thing.
Jayne Mansfield, a sex symbol for the ‘50s and ‘60s was no stranger to publicity stunts. Constantly compared to Marilyn Monroe, as a stunning blond herself, it’s no surprise that she found herself posing for the cover of playboy and even wearing the crown as Miss February 1955. She wasn’t afraid to show off what she had, and she definitely did!
At the time it was as if people couldn’t keep her name out of their mouths, so she gave them something to talk about…constantly. But being a nice silhouette to look at wasn’t her only talent. She was a singer, a nightclub entertainer, and even an actress for Fox Studios. One of her most famous roles was as the fictional actress Rita Harlowe in the Broadway play Will Success Spoil Rock Hunter? - a role that she ended up reprising for the film version.
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. Her life was well-documented on the show and it made her hugely popular at the time.
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. Her first reality series was Kendra that aired from 2009 to 2011 and that show was followed by Kendra on Top, which ran from 2012 to 2017.
Kimila Ann Basinger’s sultry bedroom eyes were the epitome of sex appeal in the ’80s and ’90s. She’s blonde, she’s thin and she had that je ne sais quoi that drove boys wild. Kim started out as a model in New York where she rocked the runways for nearly a decade. She was also married to Alec Baldwin which boosted her career even further as the relationship was highly publicized.
When asked, Kim said she was extremely shy as a child. However, that didn’t hold her back from posing for Playboy Magazine on the cover of the February 1983 issue! Ask anyone who was around in the ‘90s and they’ll tell you that they had a poster of Kim in their bedroom.
And Kim has had no regrets over her appearance in the magazine saying of Hefner, "He was not only a fearless pioneer but a generous one who saw potential in girls like myself when the timing in their careers was perfect for that particular kind of exposure (pun intended) that was catapulting, not exploitative. I will always be thankful to Mr. Hefner and Playboy for helping me at a very crucial period of time in my life and career."
“Michael’s sister in a thriller pictorial” is what Playboy said about La Toya Jackson on her 1989 cover. La Toya was a major pop sensation…along with every other member of the Jackson family in the ‘80s and ‘90s. As the middle child, she had to find ways to snag attention from her other famous siblings. Appearing on Playboy certainly helped achieve that.
La Toya didn’t just pose for playboy once, but twice! In 1991, La Toya posed to promote her New York Times Best Seller La Toya: Growing Up in the Jackson Family. So, if you thought those Playboy bunnies were all looks and no smarts…think again!
In recent years, she's been using reality television to garner attention, and hey, a job's a job.
Who doesn’t want a dash of Ginger Spice? Geri Halliwell, Ginger Spice from the popular world-phenomenon girl-group Spice Girls spiced up our lives with her cover shot for Playboy in 1998. Her cover showed her in an iconic Union Jack mini-dress showing a peek at her you know what’s! It's definitely something the boys of the '90s wanted to see, and it was a no-brainer to have at least one Spice Girl on the cover.
At the time, Geris was one of the most famous popstars in the world! Everyone wanted to be a Spice Girl. She actually ended up running out on her sisters in spice after a split-up over creative differences but rejoined the girl-group in 2007 for the Spice Girls Reunion. When your livelihood depends on publicity, we guess you’ll do anything!
But it should be noted that Geri Halliwell never actually posed for Playboy. The photos were sold to Playboy by a photographer.
You may know Dita Von Teese a little by her well-earned moniker, The Queen of Burlesque, or as the ex-wife of Marilyn Manson. Nevertheless, she's a whole lot more than that. Dita has been a trailblazer for the adult entertainment industry for decades, and she went all out for her Playboy cover. She’s a little bit of pin-up, a little bit of goth, a smidge of bondage, and a whole lot of sexy!
But Mistress Von Teese isn’t just a nice pair of legs. She’s a businesswoman, fashion designer, author and model! She’s made a whole industry out of her twisted point of view, and she’s not shy about it either. Dita is the point in which fetish meets glam, and that’s why we can’t get enough of her. She's also done some television work, appearing in CSI: Crime Scene Investigation, The Masked Dancer and The Curious Creations of Christine McConnell. Additionally, she's the author of two books.
Who said the funny girl isn’t sexy? Chelsea Handler posed for Playboy’s December 2009 issue where she was being tugged on by someone’s candy cane! Looking back on her cover, Handler wrote, "“12 years later, and I’m still screwing up xmas parties, but now with less clothes on.”
Chelsea hosted her own late-night talk show called Chelsea Lately from 2007 to 2014, which made her hugely popular at the time.
Apparently, people like to hear what Chelsea has to say because that wasn’t her only talk show! She also had a show on Netflix just called Chelsea between 2016 and 2017. We’re sure she had a lot to talk about during that horrific presidential election. In 2012, she was named by Time as one of the 100 most influential people in the world.
Kylie may be the next generation’s Kim Kardashian, she’s the youngest of the Kardashian and Jenner clans but that doesn’t mean she doesn’t have her own thing going on. In fact, she’s got a lot going on according to her eye-boggling Playboy cover! In 2019, she collaborated with her boyfriend Travis Scott, where they talked about being parents and how it has not affected their sex life.
She also told Playboy, “You can be sexy and still be a badass mom.”
Fun fact, her cover picture was shot by her boo, Travis Scott. We know what he’s looking at! Her eyes are up here Travis! It’s pretty telling that we know who this girl is without even seeing her face. We wonder if Caitlyn gave her as much crap as poor Kim when she posed for Playboy. Who knows, Caitlyn may be the next Jenner on the cover! Only time will tell.
