The 15 Most Famous Women To Appear In Playboy

"Publishing a sophisticated men's magazine seemed to me the best possible way of fulfilling a dream I'd been nurturing ever since I was a teenager: to get laid a lot."

- Hugh Hefner

If more men had the foresight of Hugh Hefner, there would be far fewer crying, babbling voicemails or misspelled text messages with a desperate tone to women across the world. They would nurture the dream to get close to a woman instead of obsess over it.

Like the Hef intended with Playboy, this article is meant to embrace the influence these women have over millions of readers. It is meant to showcase how doing the absolute minimum a woman can do (like frolicking around naked) can create such a stir, that companies will throw money at her just to do it.

The search for the most famous women to be in the magazine is over. So, put down that much more easily accessible online adult entertainment and read about that itch Hugh Hefner's dreams have scratched.


15 Pamela Anderson


Some people pick up everyone else’s slack on the job sometimes because their star just shines brighter. Archie Manning with the New Orleans Saints, Hugh Jackman on some forgettable show called Viva Laughlin, and of course, Pamela Anderson on Baywatch are perfect examples. This can’t be confirmed, but she was 99.993% of the reason anybody ever watched the show. Does anyone even remember what it was about? Wait, it was about lifeguards? That’s rich.

But let a few facts sink in for a second about how famous Pamela Anderson is. She appeared on the October 1989, February 1991, July 1992, August 1993, November 1994, January 1996, September 1997, June 1998, February 1999, July 2001, May 2004, January 2007, and January 2011 issues of Playboy. She’s appeared more times in that magazine than a "big-boned" dude at a buffet.

She was also the first Playmate to ever be knighted for her work supporting animals rights. Seems like Borat liked her for more than just her looks.

14 Anna Nicole Smith


Most people remember the sexy cartoon, Jessica Rabbit, from the movie Who Framed Roger Rabbit? With a bit of blonde hair dye, Anna Nicole Smith is probably the closest thing to her. Her looks prompted Playboy to put her on the cover of the May 1992 issue and name her Playmate of the Year in 1993.

Anna Nicole’s story is so crazy, it’s like something out of a novel. She was married to a 90-year-old billionaire oil tycoon for a little bit just before his death. He gave her all kinds of gifts including cars and a home outside Houston. After her husband died, his son and Anna Nicole fought like heck over his estate. Anna Nicole even appealed the case all the way to the Supreme Court of the United States. Ultimately, she didn’t get a dime.

If Lady Justice had taken off her blindfold and took a good look at her, the case would have probably been totally different.

13 Drew Barrymore


Corey Feldman probably shows up on a list somewhere under the titles “People With the Stupidest 80s Haircuts” or “10 Most Dysfunctional Child Actors: What Prison Are They In Now?” But the one list Feldman will definitely show up on is “People Who Dated Drew Barrymore back in the 90s Through Sheer Luck And/Or Magic.”

Remember, this wasn’t the He’s Just Not That Into You, sensible, “she probably won’t stab me” kind of Barrymore. This was the younger, crazier Barrymore who once flashed David Letterman on national television. Barrymore was so smoking hot she appeared on the January 1995 issue of Playboy, definitely getting the year started off right. The Internet claims other things happened throughout that year, but that’s not really the point.

12 Katarina Witt


East Germany gave the world a lot of things. They gave the world Red Riding Hood (this is the beer, not the children’s story by the way). They also gave the world Johann Sebastian Bach. Apparently, he was a composer of music nobody listens to. Finally, they gave the world Katarina Witt.

One of the most heralded figure skaters in the history of the world, Katarina granted the Christmas wish of perverts everywhere in the December 1998 edition of Playboy. Witt says the reason she did this was because she wanted to break this image of figure skaters as dainty little figurines. She made some headway by leading that issue to be only the second one to sell out in Playboy’s history. The cover girl for the other one? Marilyn Monroe.

11 Charlize Theron


There are things about Charlize Theron that are well known. Her Oscar win for her male fantasy-destroying role in Monster, her South African heritage, and her sweet addition to the May 1999 issue of Playboy. She's also known for her height. At 5’10”, Theron could probably throw down monster dunks right in her date's faces.

What most people don’t know is that she was discovered after getting into an argument with a bank teller in Hollywood. An agent, who wasn't trying to pick her up but was a legitimate talent scout, saw this and gave her a card to get into the modeling business and the rest is history.

The problem with her Playboy spread was that she took the photos, but sued Playboy to keep the photos from getting out. Ultimately, she was unsuccessful in her pursuit and the pics went public. For millions of men, justice was served that day.

10 Lindsay Lohan


It’s so easy to forget that Lindsay Lohan is a really funny, really talented actress. It’s even easier to forget that Lindsay Lohan can sing. One of her albums was so successful, it sold over 1 million copies, made it to #4 on the U.S. Billboard charts, and even went Platinum. One of the singles from that album even went certified Gold! This was, of course, before her well covered dabbling into that sweet nose candy.

It’s such an unusual story that a former child star would get hooked on drugs and ruin her life. There is not one documented story of that ever happening in Hollywood... yeah, right. Anyway, all is forgiven after looking at the January/February 2012 issue of Playboy. Doing her best Marilyn Monroe impression, Playboy asked Lohan to show the goods, reportedly paying her $1 million. Talk about girl power.

9 Kim Kardashian


It’s difficult to remember the days before Kim Kardashian achieved worldwide fame. Kim was once a respected community volunteer, launching charity drives and demanding equal pay for women in the entertainment industry. Ok, those things definitely didn’t happen, but it would have been nice if they did. In reality, Kim rode the wave of fame from sleeping with Brandy’s little brother and spread eagle in the December 2007 issue of Playboy.

For those that have been in solitary confinement or somehow just regained their eyesight, Kim Kardashian is one of the biggest “stars” on the planet. Her leaked sex tape, marriage to several men, and gigantic booty have given her fame that has lasted way longer than most people in show business.

What’s strange is that her barely-legal sister, Kylie Jenner, is planning on doing a spread for Playboy in the future. There’s no word on when the all-Kardashian issue of Playboy will be available. When it is, the makeup and hair removal companies that get the bid will probably see their stock shoot up 300%.


8 Madonna


Picture this: it’s 1984. A guy is riding around in his Chevy Camaro. It’s probably yellow. It has the picture of a firebird on the front. There’s a guy that’s slicking back his hair or picking out his afro while looking in the mirror. He pops into the convenience store with his stonewashed jeans and he’s especially happy because he has those 2nd edition Air Jordans on.

Nothing fazes him. It’s September. The air has that slight crisp like a chilled apple. But the weather doesn’t bother him because he has his brand new Members-Only jacket on. He’s on top of the world. When he’s buying his pack of smokes at the convenience store, he sees a woman, someone called Madonna, in a black lacy get-up and a jacket on the cover of Playboy. He buys it, thinking he’s seen it all, and then he opens the cover. Bam. Game over. Life changed.

Ironically, after releasing Like a Virgin, Madonna did the anti-virgin thing and showed up inside the September 1984 issue of Playboy. Few people have had fame and success like Madonna, though. Even though she’s at grandma status now, she is still the highest grossing touring artist of all time and has been nominated for and won countless awards. This is all after getting fired from Dunkin Donuts for squirting jelly on a customer. There are so many inappropriate jokes that can be filled in with that tidbit, so it’s best just to stop now.

7 Naomi Campbell


The scientists that built Naomi Campbell deserve a pat on the back. Give them a new car; a round of applause even. Just give them whatever they want for creating the fantasy that is Naomi Campbell. She’s the closest thing to a FemBot in this world.

What’s most interesting about Naomi are the things she does away from the camera when she’s not making people drool. She does charity work for breast cancer research, promotes diversity in the modeling business, and helps to provide education to under developed countries. She also has a ton of fragrances that will never smell as good as her.

This of course offsets the numerous legal troubles she’s been in because of her temper. Several former employees said that she acted like a drunk uncle and beat the crap out of them. This has lead to some big payouts as a result. But frankly, after seeing the December 1999 issue of Playboy, most guys would probably beat themselves up just to get close to her anyway so it all evens out.

6 Jenny McCarthy


Playboy knew what they were doing when they spread Jenny McCarthy out in the October 1993 issue. People went nuts and the magazine made her Playmate of the Year in 1994.

But what made Jenny famous though was her personality. Saying Jenny McCarthy has a personality on a list that talks about famous Playboy models is similar to talking about the chemical properties in paint. So, before shutting the laptop, understand that Playboy made her famous, but her personality made her a superstar

Remember her role in BASEketball and how funny she was? For those over 30, remember how cool she was when she was a co-host on Singled Out before MTV got terrible? Well, that’s not fair, MTV has kind of always been terrible, but Jenny McCarthy made it just a tad better.

5 Carmen Electra


If Playboy models had a football team and Carmen asked to be the quarterback, she would be. That, of course, makes absolutely no sense, but Carmen Electra can do whatever she wants. Starting out as a dancer, Carmen (formerly Tara Leigh Patrick), showed up on the cover of Playboy in May 1996 and her appearance was so hot that it put her on the path to stardom.

People will remember Carmen Electra more for her acting than her nudity. Everyone remembers her scene-stealing role in the movie Good Burger opposite Keenan and Kel. No? Well, she also did some lifeguard show, but nobody remembers its name.

She got so famous, she even hooked up with Dennis Rodman. Not surprisingly, the marriage to the nearly 7-foot tall man who wears a wedding dress better than her didn't work out. Nobody outshines Electra, honey, nobody (snapping fingers in sassy motion).

4 Kim Basinger


Linguists have still not agreed on how to pronounce her last name. Is it Ba-seen-gur? Bah-sing-her? Who knows. Even though Bay-sing-ir might be one of the oldest women on the list, it’s important to remember that getting on the front of Playboy isn’t about staying popular forever, it’s all about confidence, style, and nakedness... uh, timing!

For those too young to understand, Kim Basinger may be little less hottie and a little more cougar. But back in 1983, Kim could sell fire in Hell with her looks.

Straight off her appearance in a Bond film, Basinger bared all for the magazine. Remember, this was in the days before people could look at naked women on their cell phone in the bathroom at work... or at dinner. In those dark, dark ages, someone had to go to a convenience store, avoid the judgy stares of the sales clerk, and openly tell that stranger how perverted they were. People apparently decided to take that risk because this was one of the best selling issues for the magazine.

3 Mariah Carey


At least once in his life, every guy has been caught singing a Mariah Carey song out loud. It could have been his neighbor pounding on the wall when he was sobbing over his ex’s picture while singing “We Belong Together.” It might have been in the shower, when he thought he was alone, singing “Dreamlover” into the shampoo bottle. For the really unlucky, it might have been singing “Always Be My Baby” with his mom’s dress on. Well, singing Mariah Carey songs are probably the least of his issues if that’s happening.

The point is that Mariah Carey has such a presence with her voice, Playboy probably had no option other than to make her the cover girl in the March 2007 issue. Because she probably was concerned about her career, her privacy, or has what people call “dignity," she actually didn’t even appear nude. Mariah Carey is so private, a white unicorn is more likely to show up drunk at a nightclub dressed as a cop than she is to pose nude.

2 Denise Richards


Waiting... ok, now that Denise Richards’ old photos have been Googled furiously, please begin reading the squiggly lines here without boobs on it. In 2004, Denise Richards’ warmed up the winter when she showed up on the December issue of Playboy. The craziest part is that she just had a baby before taking the photos! Well, not just had a baby. That’s a whole different, scarier article.

Despite how fantastic her pictures were, Denise isn’t all sugar and spice. In 2006, some paparazzi snuck onto a set of her (non) Oscar-winning movie, Blonde and Blonder, and tried to take some pictures of her. The former Mrs. Sheen went ape scat and grabbed a laptop one was using and threw it… hitting an 80-year old woman. The old lady didn’t press any charges though; probably because she saw the December issue too.

1 Marilyn Monroe


It was the December 1953 Playboy Magazine #1. The original. The standard bearer. Marilyn Monroe’s status as the most famous person to ever show up in Playboy is undisputed. At least two of the women on this list tried to copy her style. Every celebrity with blonde hair and a curvaceous figure is compared to her.

Only two editions of Playboy have ever completely sold out. The issue with her in it was the first. The second one didn’t happen for nearly another 40 years. She set the precedent. There’s no mistaking it. Her status is so big, she's like the Shaquille O’Neal of nude models. Now, try and enjoy that mental picture the rest of the day.



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