If you had the right look, a healthy dose of confidence, and the right personality, you could almost make posing for Playboy your full-time career. Each year, a centerfold is chosen as "Playmate of the Year" and given $100k and a brand new car — not a bad payday for getting half-naked!
Heather Kozar poses for her 1999 Playmate of the Year photoshoot in this photo, but that wasn't the first time she graced the pages of Playboy. A Year previous, she was crowned Playmate of the Month in January 1998. Aside from lewd modeling, Kozar is best known for her work on The Price is Right, a popular game show.
You might have to throw on a pair of bunny ears to get in, but the Playboy mansion has never been a place completely exclusive to the rich and famous — or even exclusive to legal adults! One Reddit user shared this old photo of his grandfather posing with some bunnies at the mansion. The real kicker? He was just 16 when the photo was taken!
Everyone and anyone wanted to get into the Hugh Hefner's house to prance around with bunny-ear-clad girls, but there are still many rumors surrounding exactly what it takes to get into the mansion in the first place. According to VivoMasks.com, there are five ways to visit the mansion. 1. Have a personal invitation from Hefner (unfortunately, that option is no longer available). 2. Work for Playboy Enterprises. 3. Be attractive, especially when you're female. 4. Be famous. 5. Win tickets in a Playboy-sponsored raffle.
Swedish model Victoria Silvstedt became a staple of the Playboy company after appearing on the cover of their December 1996 issue. She is a woman of many accomplishments, including modeling, acting, singing, and appearing on television. In fact, she participated in the Miss Sweden beauty pageant at just 18 years old!
After Miss Sweden, Silvstedt signed up with a Parisian modeling agency, eventually working with the likes of Chanel, Dior, Armani, Givenchy, and Valentino. Her modeling caught Hugh Hefner's attention, who crowned her Playmate of the Month in '96 and then Playmate of the Year in '97.In this photo, Silvstedt poses with a copy of Playboy magazine after winning the title of Playmate of the Year in 1997.
This photo was taken at a 1986 party in the Los Angeles Playboy mansion. In it, Hugh Hefner poses with Carrie Leigh (on the right). If you didn't know, Carrie Leigh is an actress born in Ontario in 1963. She's best known for the movies A Fine Mess, Beverley Hills Cop II, and Blood Relations. Leigh was 19 when she met Hefner in Canada and later garnered the reputation of being one of his many lovers from over the years.
The ex-Playboy Bunny lived with Hefner in the Playboy Mansion for 5 years in the 1980s, and they had their fair share of drama. After leaving the mansion, Leigh filed three lawsuits against the magazine mogul for publishing unauthorized photos of her. Plus, she reportedly said living there was "almost like a cult," according to Hollywood Life. She said, “When you live in an environment like that, that’s so different from how other people live, you start forgetting who you are and what you believe is right.”
When Eugena Washington was chosen as Playboy's 2016 Playmate of the Year, she made history in two ways. She was the first PMOY after the magazine's controversial decision to end their controversial nude centerfolds, and she was the last winner to be announced by Hefner before his death in 2017.
In this photo, Hefner and Washington pose for the cameras at the conference announcing her win. Eugena Washington — born in South Carolina — was the second runner-up in Tyra Banks's reality show America's Next Top Model, Cycle 7. After her 2016 Playboy appearance, rapper B.o.B. invited Washington to appear in their music video for "Nothin' on You."
Before there was the Hollywood Playboy mansion, there was the original Chicago mansion that only true fans of the franchise remember. While it may not have the same iconic status, it was the hottest, hedonistic party spot during its day. Although abandoned by Hefner, the OG mansion is still worth a pretty penny today (upwards of $3.5 million!).
In this photo, we see a group of people enjoying themselves at a party hosted by Hugh Hefner in 1961. Unfortunately for any fans in Chicago who want to visit the "historic" landmark, the new owner converted the building into simple condos. Perhaps another lewd magazine mogul will swoop in and purchase the mansion one day to keep the party spirit alive.
The Grotto is the part of the Playboy mansion where all the fun occurs (where all the rumors start). We won't get into all of the gory details, but we're sure you can imagine what goes down. Popping champagne bottles, bunny suits, and "completely legal" activities... The whole nine yards.
In this photo, two unknown women pose in the Grotto at a 2008 party. This famous rock-covered pool has been host to many famous people and important moments that there's not enough time in the world to describe everything that's happened there. It's truly legendary!
If you had the money, the Mansion was available for private events — no matter how misguided they might have been. In this photo, we see a shot from a 1990s bar mitzvah. It takes some real chutzpah to have a religious party surrounded by women in bunny ears.
Obviously, this practice is one of the most problematic things to go down at either of Hugh Hefner's mansions. There's no reason anyone under 18 years old should attend his parties, especially when the content is explicitly lewd.
Sure, there was plenty of partying going on at the Playboy mansion back in the day, but that wasn't the whole story. Some celebrities would actually stop by for a higher cause than seeing scantily clad women (sometimes). You heard that right! Hugh Hefner hosted various charity events on his property with the likes of A-list Hollywood heroes.
This photo features actress Farrah Fawcett as she poses during a charity tennis tournament in 1976. Aside from her iconic hairstyle, Farrah Fawcett was a four-time Emmy nominee and six-time Golden Globe Award nominee. It all started when she starred in season 1 of Charlie's Angels, and the rest is history.
If Roseanne can look good in a bunny outfit, then literally anyone can. It will never cease to amaze you what you find at the Playboy Mansion, especially from back in the day. This photo of Barr was taken in 1994 at "The Hoppening" — a cleverly named AIDS benefit even hosted by Hugh Hefner himself.
If for some reason you aren't aware, Roseanne Barr is the now-infamous actress known for her titular sitcom from the late '80s and '90s. While she wasn't controversial back then, she landed herself in hot water after posting a tone-deaf tweet referring to former Presidential advisor Valerie Jarrett as an "ape" on Twitter.
Here, 2001 Playmate of the Year Brande Roderick poses in front of her new Boxter Porsche. Roderick is both a model and actress, best known for her work on Baywatch and — of course — posting for the Playboy centerfold. Before she secured the title of Playmate of the Year, she won Playmate of the Month in April 2000.
2003 marked the 50th anniversary of Playboy magazine, and Hefner wanted to make the anniversary year one that readers would never forget. In this photo, Hefner poses with some aspiring models who hope to be chosen as the magazine's 50th anniversary Playmate.
Colleen Shannon snagged the title of 50th's Anniversary Playmate of the Year as well as the magazine's Playmate of the Month in January 2004. The Alaska-born D.J. has performed with countless artists, including Snoop Dogg! Aside from Playboy videos, she's appeared in TV series like How I Met Your Mother and Miss Cast Away and the Island Girls.
You might not peg Hefner as a family man, but in this photo, we see him with his daughter, Christie, at the 1982 Playmate of the Year luncheon. Hefner actually had four children during his life. Christie (pictured) worked as the CEO of Playboy until 2009. Her half-brother, Cooper, also acted as CEO of the company until 2019 when he joined the Air Force.
Hefner's daughter, Christie, is a successful American businesswoman and activist in her own right. In fact, she worked hard enough to secure the seat of chairman and CEO of Playboy Enterprises from 1988 to 2009. Sure, she had it easier than other kids aren't the daughter of a magazine mogul, but she still deserves praise for her dedication to the family business.
Hugh Hefner and the Playboy Mansion played host to many famous guests, but in the 90s, the tables turned — they were the guests on one of the hottest sitcoms of the time! That's right, The Fresh Prince of Bel-Air featured the magazine in the season 4 episode of "Fresh Prince After Dark."
During this episode, Will and Carlton tag along to meet Hugh Hefner when Hilary goes to the mansion to pose for Playboy. During an interview published in the magazine, Will Smith commented on his portrayal of Muhammad Ali in Ali (2001): "I was born to play Ali. I felt like there was nobody in the world who could do this but me."
As stated previously, Hugh Hefner hosted countless celebrities and stars during his life at the Playboy Mansion, but not every famous person who visited the property kept their reputation squeaky clean in the years after their stay. Case in point: O.J. Simpson. Here we have a pic of the infamous athlete and actor as he visits the mansion in 1979. If only he knew what the next 30 years would bring for him...
Before his highly publicized criminal trial in 1994, Simpson was best known for his professional football career. Nicknamed "Juice," he quickly threw away his stellar reputation when he was arrested and charged with the murder of Nicole Brown Simpson (his ex-wife) and her friend Ron Goldman. Simpson managed to nab an innocent verdict, but that didn't stop him from landing in jail a decade later.
Garrett is a former child actor and teen idol who gained popularity in the '70s and later managed to revive his acting a music career after a brief hiatus from 1986 to 1995. Unfortunately, he's another celebrity guest who landed in some hot water. From legal troubles to rampant drug use, it's safe to say that Garrett — while beloved for his music — probably wasn't at the Playboy Mansion for a charity event.
We're not sure why anyone would come to the Playboy mansion except to party, but if you find yourself in that situation, there's actually a lot on the property that doesn't have to do with sex or booze. In this photo, we see a shot of the gaming room in the mansion — including two Playboy-themed pinball machines.
Back when the mansion called Chicago home, Hefner dedicated an entire room to games, another to bowling, plus an array of other random things. In fact, the mansion used to be a college dormitory after Hefner rented it out to students of the Art Institute of Chicago as "Hefner Hall." The school used the building up until 1990.
If you're visiting the Playboy mansion, you never know who you're gonna meet there. Sure, it will probably be celebrities and models — but which ones actually dared to enter those haunted halls? If you happened to be there in 1999, you might have run into a few famous actors as shown in this photo.
Here, actor Vern Troyer, who was in the middle of a celebrity blow up thanks to Austin Powers, poses between two Playboy Bunnies. And who's with him? None other than Playmate royalty, the Bernaola twins. There's really no telling what will happen or who you'll see at the mansion!
In this photo, Pamela Anderson and then-boyfriend Bret Michaels pose at a charity gala hosted at the Playboy mansion. Yeah, we have a hard time believing they were more interested in "charity" than partying, especially dressed like that! Despite our doubts, Playboy-endorsed philanthropy was probably incredibly successful given the number of high-profile guests Hefner attracted.
Hollywood bombshell Pamela Anderson was a staple not only at the mansion but also in Playboy magazine. She appeared in numerous issues. Plus, in 2015, she was the last model to appear nude in the centerfold before upper management banished the practice entirely. It truly was the end of an era. obably incredibly successful given the number of guests Hefner attracted.
Press is no fun, but it's inevitable for any celebrity with an ounce of fame. So if you've got to tell yourself out to the paparazzi anyway, why not do it in style at the Playboy Mansion? That's what actors like Shannon Malone and Corey Feldman had in mind here as they pose for a quick mid-party photo op.
In this photo from 2000, we see the actors actually posing for the press at the mansion. But this photo is nothing like what you'd see on the red carpet: lip biting, half-drunk alcohol, and a dress eerily similar to lingerie. But we're not here to judge them... Well, perhaps we're judging just a bit. But aren't we all?
What's better than one Playboy Mansion? Two, of course! In Hefner's eyes, bigger is always better. Before the famous Hollywood location, there was the Playboy Mansion in Chicago. Hefner bought the place in 1959, and, even after the purchase of the second mansion, still split his time between the two residences during the '70s.
This original mansion didn't have quite as much glitz and glamor of the current Hollywood mansion, but there were still plenty of amenities and lots of space to throw some pretty wild parties. The property was sold in 1993 and turned into condos, but we'll never forget its place history.
Here, we see an aerial view of the Playboy mansion taken in 2005. Naturally, you expect it to be massive, but this is impressive even for the wildly rich. Watch out, Jeff Bezos! You might be rich, but your house will never be as iconic as Hefner's Hollywood property.
In addition to countless pools and bars, the mansion is also home to a zoo, a basketball court, and a pipe organ. The property allegedly requires a staff of 80 to maintain. While we do miss the charm of the OG Chicago mansion, there's no outdoing the Hollywood version. Do you know anyone that has a zoo in their home?! We didn't think so.
The Playboy Mansion has been known as a "hot spot" for concerts, ragers, charity events, and press parties throughout the years, as well as a place to promote your next big project. This photo manages to do capture the energy of the average Playboy-endorsed concert. Just look at how many people are packed in there!
In this photo, we see Sean "P. Diddy" Combs performing a 2010 concert at the mansion to promote the upcoming film Hot Tub Time Machine. The movie might have been just average, but this party was clearly popular enough that nobody cared if the movie flopped or not after partying with P. Diddy.
It wasn't enough for Hefner to just throw house house parties at the Playboy Mansion — some of them had to be full-on "experiences." The effort that went into creating a Playboy party were truly a sight to behold. From themes and decor to simply catering the events, Hefner spared no expense.
In this photo from 2015, we see the property getting decorated for the annual Halloween party, which we're sure was some spooky fun. As with any relatively big house, people spread rumors about the Playboy Mansion being haunted, especially after Hefner tragically passed away. Whether or not those rumors have any merit, they still throw some banging Halloween parties.
As you might imagine, things can get pretty crazy at the Playboy mansion, and we probably don't have to explain "how" or "why" that would be. It's not like the place is known for wholesome family fun or high-brow activities that prioritize peace and quiet. Any normal person who knows anything about the mansion probably pictures something like this when they think of Hefner's parties:
This photo was taken at a party in the original Playboy mansion in Chicago. In it, an unknown guest is either making a dash to the pool or is making a break for it to get away from this super creepy guy that grabbed her towel. We're not here to scold anyone, but this makes us a bit uncomfortable even if it was all in good fun.
Here is a shot from yet another wild night at the original Chicago-based Playboy Mansion. As if their hair wasn't enough indication, the photo was taken in 1961 when bigger was better and mod fashion took the country by storm. In the photo, two unnamed guests at the mansion cuddle up in fur, and we doubt they're wearing much beneath the covers.
According to CultureTrip.com, Hefner "credits his start in Chicago with making Playboy what it became. If anything, the Los Angeles mansion drew every inspiration from the ‘humble’ abode that still sits on 1340 N. State Pkwy. " Hefner started the magazine in his tiny city apartment, building up his multi-million dollar business from there.
In this photo, Shannon Tweed poses in the Playboy mansion after she was named Playmate of the Year in 1982. Tweed is a Canadian actress who famously dated Hugh Hefner in the 1980s. As one of the most famous erotica actresses, she is best known for her performances in the niche "erotic thriller" film genre.
Tweed is also remembered for her work on the reality TV series Gene Simmons Family Jewels as she married the Kiss bassist in 2011 after her breakup with Hefner. The two dated for upwards of three decades before finally tying the knot. They share two children, Nicholas Adam and Sophie Alexandra.
As we all know very well, the Playboy Mansion was famous for its large, lavish gatherings — usually raging parties — but some of these get-togethers were sometimes actually sponsored by Hefner to draw attention to a good cause. For example, in this 1994 photo, comedians Whoopi Goldberg and Robin Williams pose together for Playboy's Children of the Night charity fundraiser.
The Children of the Night fundraiser is a wildly profitable charity event that Hefner staunchly supported until his final breath. While he was open about his sexuality, he vehemently opposed children being involved in the sex industry. This charity is a non-profit that "providers intervention in the lives of children who are sexually exploited and vulnerable to prostitution and pornography," according to The Things.
The annual crowning of a new Playmate of the Year was a big to-do at the Playboy mansion. It often featured a massive celebration and lots of press. And did we mention that the winner gets a giant cash prize and a brand-new car when they win? Oh, yeah, we already told you that... but it's still crazy!
In 1995, model Julie Cialini was chosen for the honor. She poses with a blowup of her winning Playboy cover in this photo. Cialini previously won Playmate of the Month in February 1994 before Hefner crowned her the girl of the year in '95. And no wonder Playboy loved her so much... just look at her!
The Playboy Mansion not only attracted the rich and famous, but it brought in people from all walks of life. There was never any telling who you might see there, from the likes of your regular Joe Shmoe to literal race car drivers. And we all know how much Hefner loved cars... almost as much as he loved women in bunny costumes!
In this photo, Brazilian racer Bruno Junqueira poses with some of the Playboy bunnies in front of his car. But it's not just any luxury vehicle. It's a certified Formula 300 vehicle custom built for the IRL IndyCar Series. Junqueira is a Formula 3000 champion and Champ Car World Series three-time runner-up.
As time went on, the Playboy mansion became a hot spot for Hollywood businesses, launch parties, and premieres. In this photo — which was taken in 2017 — two playmates pose at an Amazon launch party. In a contraption that's supposed to mimic a Playboy magazine cover. Pretty clever!
That night, guests were celebrating the new Amazon original series American Playboy: The Hugh Hefner Series, so it's only natural that they invited a few Playmates to tag along and entertain the crowd. Who knows just how many wholesome businesses had their launch party hosted by the sex mogul himself, Hugh Hefner.
This is one of the few photos where Paris Hilton is upstaged by her partner — and in this case, that partner isn't a hunky rich man or a ditzy blonde, but happens to be a white parrot. Only at the Playboy Mansion! And we doubt it's her parrot. Remember, Hefner has a fully stocked zoo in his backyard!
That night, Hilton was visiting the mansion for a wildlife fundraiser called "Parrots in Paradise." Hence the bunny theme, Hefner obviously had a big heart for wildlife. What would the Playboy franchise be without the infamous rabbit-related branding? We can't even think of it, it's too weird!
Ryan Seacrest has hosted some memorable gigs, but most probably don't compare to when he was chosen to announce the 2003 Playmate of the Year. Now that's a pretty fabulous job opportunity! And who's Seacrest to turn down such a big opportunity, so of course he did it despite hordes of disapproving American Idol fans.
In this photo, Seacrest and Hefner meet at the Playboy Mansion before making the big announcement. That year, Christina Santiago snagged the title, the money, the car, and the prized centerfold photo shoot. She is also known for her modeling, acting, and multiple stints as a Playboy bunny.
It wouldn't be a Playboy Mansion party without a woman removing some — or all — of her clothes. And in 2003, burlesque icon Dita Von Teese was more than happy to oblige. What else are you going to do at a Hefner party... chit-chat over wine and cheese for a few hours? We don't think so.
In this photo, DVon Teese performs for Hefner, his bunnies, and his guests at the launch party for Spike TV. Otherwise known as Heather Sweet, Von Teese is a celebrated vedette, burlesque dancer, businesswoman, and model. She is best known for her burlesque performances and for re-popularizing the genre. Hence, she was titled the "Queen of Burlesque" by her fans.
It might seem strange to think of Playboy as a family business, but several of Hefner's children have had a hand in running the company. We've already talked about Christine's stint as chairwoman and CEO of the company, so what about the others? Here, Hefner's son, Cooper, poses with Dani Mathers, who was chosen as the 2015 Playmate of the Year.
Cooper Hefner worked as both the chief creative officer and chief of global partnership at Playboy. He's credited for reintroducing nude images to the magazine after its ban in 2015, stating that "the problem had been the presentation... rather than the nudity itself," as reported by The Hollywood Reporter. He also included the first transgender Playmate in the centerfold back in 2017.
Playboy is all about spectacle, so it's no surprise that Hefner wanted to dazzle guests from the moment they walked into the mansion. This photo shows what guests see when they walk into the lobby of the mansion. If you ditched the oil painting of the famous pornographer in the back, this could look like anyone's entryway.
According to Culture Trip, the decorations of both the Chicago and Hollywood mansions are 50% of why they're so iconic. And we agree! They write, "The mansion was opulently decorated in some of the most outrageous decor for the times, further solidifying [Hefner]’s overarching aesthetic of sex chic. Even the sign on the door read, Si Non Oscillas, Noli Tintinnare, which translates from Latin to “If you don’t swing, don’t ring.”
Only at the Playboy Mansion can you brush elbows with one of the most famous musicians of all time AND maybe a wild animal or two! In this photo, Diana Ross poses with a chimpanzee while she attends the mansion's annual Safari Brunch in 2004. Who here has ever attended a safari brunch?!
If you don't know, Diana Ross is an iconic singer and actress best known for being the lead singer of The Supremes, one of Motown's most successful groups in the '60s. In fact, they are one of the most successful female vocalist groups to this day. With twelve #1 hit singles, they are the best-charting girl group in history.
The Mansion might have been Hugh Hefner's home, but I don't think anyone is gonna argue that Snoop Dogg looks out of place in this venue known for beautiful women and debauchery. In fact, we'd be more surprised if he wasn't at every Playboy event since the beginning.
In this photo, the rapper poses with some of the Bunnies at a Mansion party sponsored by Snoop Dogg and Colt 45 because why not? You know when both Hefner and Snoop Dog are at a party, it will be a rager. Not that we know either of them personally, but it's a safe guess.
Hugh Hefner died on September 27th, 2017, due to a sepsis infection. While some people just wrote him off as a pervert selling nudie mags, he made an impact in both the world of publishing and politics. And don't forget about the millions of dollars he donated and raised for multiple charities throughout the years.
This photo shows a makeshift memorial that fans created at the gates of the Playboy mansion a day after his death. While there's a lot you can assume about the guy, nobody can say he wasn't influential or wasn't generous with his home, time, and money. Rest in peace, Hugh. May you frolic with bunnies in heaven forever.
