Playboy magazine is as much a staple of American history as baseball and apple pie. It has been around since 1953 and over the years it has featured some of the most beautiful women in the world. In most cases it has helped launch the career of someone that went on to major success on television and movies. Playboy is also known for fostering great relationships with their models, and many of the women kept some ties to the company for many years after their photo shoot.
A few women have had good careers prior to appearing in Playboy, and that’s exactly what drew attention to them, but overall there is no doubt that the company has helped launch some fantastic modelling and acting careers.
There was a time during the 90s that it seemed like Playboy must have had a contract with the television series Baywatch. Whenever a cutie appeared nude in the magazine she ended up on the show shortly thereafter, usually within the year, not that we're complaining!
Just a couple of months ago Playboy stopped putting nude photos in its magazines. The women posing provocatively are still there, but they are no longer nude. Despite what they may say, the real reason for this is that the internet has changed the world that we live in. There is no longer a need to buy the magazine to see the photographs when one click online can get you there for free.
It is only fitting with a company with as rich a history as Playboy has, to have us look at 10 of the best models of all time, and see how they're looking in 2016! While some have aged beautifully, you're also going to learn that not everyone was quite so lucky!
Don't worry though, these are still 10 of the sexiest women to ever appear in the magazine. As you're also going to find out through some research, these women also were comfortable to let it all hang out! Enjoy!
20 Angela Little (then)
One look at her and it is clear to see why Angela was voted as the Playmate of the Month for August of 1998. As well as being named the PotM, she has been in several Playboy videos as well. While 1998 may have been her most prominent year, she did steady work for the company for five years after she was a centerfold.
The native of Alabama has also appeared in several major movies including American Pie: Band Camp, Walk Hard, My Boss’s Daughter and Rush Hour 2.
19 Angela Little (now)
Angela Little, now 43, continues to guest star on several television series. She has been on The Bold and the Beautiful, Buddy Faro, Reno 911!, Cold Case, CSI, Malcolm in the Middle, Charmed, Nip/Tuck and Monk. She also hosted E!’s Wild on the Windy City.
She was married to Andy Mackenzie for several years, but they are no longer together.
18 Karen McDougal (then)
Karen McDougal was Playboy’s Playmate of the Month in December of 1997, and perhaps not surprisingly, was then named "The Playmate of the Year" in 1998. She was also voted as the #2 Sexiest Playmate of the 90s by readers in 2001. Prior to winning a swimsuit competition that launched her modeling career, she was a pre-kindergarten teacher. Can you imagine the happiness of those dads when they saw her? That’s just not something that happens every day.
She has been in several commercials over the years and has landed a lot of minor acting roles, but she mostly keeps a very private life.
She was also very successful as a fitness model and was the first woman to be on the cover of Men’s Fitness Magazine.
17 Karen McDougal (now)
Karen McDougal is now 45 years old and is an avid collector of cars and motorcycles.
In 2001, when the XFL was launched, they used her in several commercials for the league on NBC. The commercials implied nudity and were eventually pulled for being too risqué. The league only played one season.
In 2004, she participated in the WWE Divas Search and made it to the last round. She was eliminated just before the final 10 participants were named.
McDougal has also made appearances on the TV show Anger Management as well as several other shows. She has also made many cameos in movies including Charlie’s Angels, Joe Dirt, and The Girl Next Door. David Lee Roth has brought her in to appear in one of his music videos as well.
She was linked to a romantic relationship with actor Bruce Willis for a time but since she is so private not a lot is known about her personal life.
16 Kelly Monaco (then)
Kelly Monaco appeared in Playboy for its April 1997 issue and landed a role on the ABC soap opera Port Charles later in 1997. She stayed with the show until it was cancelled in 2003. She then joined the cast of General Hospital and is still on the show today.
She also appeared, and won, the first season of Dancing with the Stars.
Before she started on the soap operas she got her first TV role on the show… you guessed it, Baywatch. Monaco also appeared in three movies during the late 90s. She was nominated for two Emmys for her work on the soap operas, but didn’t win either time.
15 Kelly Monaco (now)
In 2009, Monaco, now 39, was a judge for the Miss USA pageant and she also had a six month run in the play Peepshow. It played at the Planet Hollywood Resort and Casino in Las Vegas. While she apparently did an outstanding job, she was replaced by Holly Madison when her contract expired.
She has also appeared in several issues of Maxim Magazine and in 2009 was named their sexiest cover model of the decade.
In 2011, Monaco kept busy by being the star of an E! reality show called Dirty Soap.
She returned to Dancing with the Stars for their 15th season and finished in third place.
14 Erika Eleniak (then)
Erika Eleniak is another in the long line that went from a Playboy appearance to the television show Baywatch. No wonder the show had such good ratings. Someone was clearly onto something there.
At the age of 19 she was in Playboy in June of 1989 and in July, she became the Playmate of the Month. After making several appearances on the television show Charles in Charge she moved on to Baywatch and also made an appearance on Full House.
She got her start in film however before she posed for Playboy. In 1982 she made her film debut in E.T: The Extra-Terrestrial and then later she was in a remake of The Blob.
Eleniak also had roles in the movies Under Siege and The Beverly Hillbillies as well as several others.
13 Erika Eleniak (now)
Erika Eleniak, now 46, has continued to make television appearances and she was a cast member on the reality show The Real Gilligan’s Island in 2005.
In 2006, she was fighting weight issues and was on the reality show Celebrity Fit Club that aired on VH-1. Later on that year she was on a British comedy podcast called 80’s Movie and Music Fest Café where she talked about both Baywatch and her time on Celebrity Fit Club.
In 1998, Eleniak married Philip Goglia, but divorced him after just six months of marriage. She was last tied to Roch Daigle, a key grip that she met while filming Snowbound in 2001. They had a daughter in 2006 and it appears that the couple are still together today.
12 Pamela Anderson (then)
Pamela Anderson has been in Playboy numerous times, but things weren’t always glamorous for her. Just a couple of years ago she announced that as a kid she was sexually abused many times by both men and women. A female babysitter abused her from the ages of six through ten and when she was 12 years old she was raped by a 25-year-old man. To top that off she was gang raped by her boyfriend and six of his friends at the age of 14. She suffered some serious trauma that could have led her life in a totally different direction, so you have to give her a lot of credit for being able to be as successful as she has been.
She was discovered by a talent scout while being at a CFL football game in 1989. She was at a BC Lions game wearing a Labatt’s beer t-shirt and she ended up on the jumbotron. They sought her out and hired her as a spokeswoman for a short time.
Shortly after that she was in Playboy’s October 1989 issue. She has appeared in the magazine many times since then.
She also played “Lisa, the Tool Time girl” on the television show Home Improvement and then moved on to her most famous role as “C.J. Parker” on Baywatch.
In 1993, she was also in the Vince Neil music video “Can’t Have Your Cake”.
11 Pamela Anderson (now)
Pamela Anderson is now 48 years old and still very active. She has been on numerous versions of the show Big Brother including variations of the game show held in India, Bulgaria and the United Kingdom.
In 2010 she took part in Dancing with the Stars and lasted for seven weeks before being eliminated. She came back in 2012, but was ousted in the very first week. She used those experiences to partake in the British version of the show, Dancing on Ice, but was booted off in the first week.
Anderson is a huge supporter of PETA and she has been involved with countless campaigns for them. She is also very active with AIDS and HIV support as well as with the American Liver Foundation.
10 Jenny McCarthy (then)
Jenny McCarthy began her career with layout in Playboy in 1993 and was later named the Playmate of the Year. She turned that publicity into a long and successful acting career. She was paid $20,000 for the photo shoot and was selected out of more than 10,000 other women.
In 1995, she joined MTV to co-host the singles dating show that was called Singled Out. After that she made a few appearances with the WWE before getting her own show, twice. The Jenny McCarthy Show aired on MTV and then Jenny aired on NBC.
She has appeared in lots of television shows and movies as well. Her big break on the silver screen came with her role in the film BASEketball.
She made several more appearances in Playboy. Clearly it was a positive experience, as her sister Amy has also posed for the magazine.
9 Jenny McCarthy (now)
McCarthy, now 43, has continued to appear on several TV shows and was in an online series called “In the Motherhood” that later aired on MSN. Along with being in two video games she has also been a co-host on several Dick Clark’s New Years Rockin’ Eve shows on ABC. She was even a co-host on the show The View on ABC for about a year.
McCarthy continues to be one of the top choices on television whenever a new show needs a host.
8 Donna D‘Errico (then)
Donna D’Errico is another woman that turned an appearance in Playboy into a television career. After she was the Playmate of the Month in September of 1995, just like Pamela Anderson and several others did, D’Errico got a role on the TV show Baywatch.
Before she was in Playboy she had a limousine company in Las Vegas. She also owned Zen Spa, a day spa in California and also appeared in several movies.
She was married to Nikki Sixx of Motley Crue for nine years.
7 Donna D’Errico (now)
D’Errico, now 48, is still able to be quite active! She gained some publicity after she attempted to climb Mount Ararat in Turkey, but she suffered an injury after a fall and had to return home. She made a documentary about the experience.
In early 2014, she filed for bankruptcy and it was revealed that Sixx was paying her monthly support of $7,800 in addition to 5% of all of his earnings. According to Radar Online, that amounts to about $2.1 million per year.
When she made the documentary about her climb she used Kickstarter to fund it and raised $11,000.
If things are that tough she can always go back to acting or cut a few expenses. $2.1 million a year is serious money. How can someone not live on that?
6 Shannon Tweed (then)
Shannon Tweed took a different road to Playboy stardom. She was on the Canadian television show Thrill of a Lifetime and they set up her first photo shoot with the magazine. She was Playmate of the Month for November of 1981 and then was chosen as the Playmate of the Year in 1982. She also did a layout with her sister Tracy for the magazine.
Tweed became a constant on television appearing on shows such as 1st and Ten, Falcon Crest and “Frasier” as well as appearing in several movies. She also made appearances on Married with Children, The Dukes of Hazzard and had a long role on Days of our Lives.
Since 1984 she has been in more than 60 movies including one produced by Gene Simmons that was called Detroit Rock City.
Tweed and Simmons were featured in a long running TV reality show that was called Gene Simmons Family Jewels. The show was about their life away from the stage and television/movie sets.
5 Shannon Tweed (now)
In 2010, Gene Simmons Family Jewels was filming in Shannon Tweed’s home town of Saskatoon, when Shannon got a special honor. The now 59-year-old was presented an honorary street sign by the Saskatoon City Council that said “Tweed Lane”.
Tweed also narrates the reality show Ex-Wives of Rock and she has a video game called Shannon Tweed’s Attack of the Groupies. Her voice and likeness are in the game.
After being together for 28 years Tweed and Simmons finally got married in 2011. The wedding was held at the Beverly Hills Hotel.
4 Elle Macpherson (then)
Elle Macpherson is the definition of the word Supermodel. Everywhere you look you can find her and her talents extend to different platforms. She’s an actress, model, producer and businesswoman.
She has been on the cover of the Sports Illustrated Swimsuit Issue five times, more than any other model.
Macpherson was the executive producer and host for Britain and Ireland’s Next Top Model and NBC’s Fashion Star. She hosted an episode of Saturday Night Live and made several appearances on the hit show Friends. She even co-hosted the 2001 Miss Universe pageant with Naomi Campbell.
She had roles in several movies and after her 1994 nude appearance in Sirens, everyone wanted to see more nude photos of her. So she got together with Playboy so they could be done “on her own terms.”
3 Elle Macpherson (now)
Elle Macpherson is now 52 years old and still going as strong as ever. She started her own company that she called Elle Macpherson Inc., which has done several projects over the last twenty years. One of her best projects was a calendar each year that was accompanied by a “Making of” television show. She also started a line of workout videos.
She has a line of lingerie that has become a best seller around the world and she is involved with several other businesses as well. In 2007 BBC Television featured her in a documentary on the show The Money Programme. It followed her day to day business dealings as she continued to grow her lingerie business around the world.
In 2009, Macpherson was the keynote speaker for the International Trademark Association’s annual meeting. It’s obvious that whatever she gets involved with, she makes successful.
For a lot of women, Playboy was a major part of their career, but not for Macpherson. For her it’s just a footnote of a very successful career.
2 Cindy Crawford (then)
Cindy Crawford has been one of the most successful models in the business for the last 30 years. She has been on hundreds of magazine covers and in 1995 Forbes Magazine named her the “highest paid model on the planet.”
The estimated total of covers that she has appeared on is over 600. Any magazine that is or has been in business has probably used her at least once. Crawford has also done spokes person work for countless companies over the years.
She is known for her famous mole near her mouth, but when she first started modeling they were removed from any pictures that she did. Now it’s probably the most famous mole in the world.
Crawford has been on many television shows and at one point she was the spokesperson for Pepsi. For a while, one thing was for sure, every time a Pepsi commercial aired Cindy would be on your TV again.
She made her Playboy debut in 1988, and did a second photo shoot with the magazine ten years later. Playboy later ranked her as the #5 Sexiest Woman of the Twentieth Century.
1 Cindy Crawford (now)
Cindy Crawford, now 50 years old, quit modeling full time in 2000 and now when she does appear in a magazine it’s a rare treat.
She has her own furniture line as well as a home goods line that sells in J.C. Penney stores. She is a very smart business woman and rarely fails with new ventures.
In 2009, she appeared on the cover of the coffee table book Room 23 and she also wrote the dedication in it.
Crawford did make a return to some modeling in 2011, and she helped with a book about her life that came out in 2015. She appeared on the April 2016 issue of Vogue Paris with her daughter Kaia.
She was married to Richard Gere in a highly publicized relationship that lasted from 1991 until their publicized divorce in 1995. Three years later she married Rande Gerber who is a former model, the two are still together today and have two kids.