Which beloved children's author was a regular at the Playboy Mansion?
Which legendary rock band got absolutely trashed at this monument to decadence?
Some of the regulars at Hugh Hefner's residence may just surprise you.
It's no exaggeration to say that Jenny McCarthy has Hugh Hefner to thank for kickstarting her
career. She came from humble beginnings, but she dreamed of the A-list from a young age.
After spending two years at college, she snagged a job in Chicago at a Polish grocery store,
hoping to jump-start her modeling career on the side.
After being informed that she was "too fat" by one agency, she left feeling dejected,
but then she spotted the Playboy building by chance. As she recalled to The New York Times,
"Something drew me there."
Upon Hefner's death in 2017, McCarthy revealed on her radio show that after
spotting the Playboy offices that day in 1993, she waltzed inside and asked what she needed to
do to land an opportunity with the magazine. Lo and behold, after taking some test shots,
she went on to become Miss October that year. She then moved into the mansion shortly after
her centerfold appearance. Unfortunately, after a few months, she realized she needed to move
out due to her hometown peers denouncing her career choice. As she explained,
"I had to move on. The highest you can do is Playmate of the
Year. There is no Playmate of the Century."
"My centerfold is me going… And they got me."
"And you got it." "Hef said-"
"I didn't know you had to audition for a centerfold."
It may seem hard to believe that a beloved children's author once lived within the walls
of the Playboy mansion, but The Giving Tree author Shel Silverstein really did spend some time there.
The iconic writer's college days were rather bleak before he served in the Korean War:
one school gave him the boot, and he decided to drop out from another. On top of that,
he once mused that he, quote, "didn't get laid much." However, that would eventually change
after he returned to America and landed a job as Playboy's "cartoon-drawing foreign correspondent."
Once Silverstein moved back to Chicago, where the Playboy Mansion was situated at the time,
he became a part of Hugh Hefner's "inner circle."' He lived in the mansion for an
extended period and entertained the revolving door of guests. This fame also meant that
women suddenly looked at Silverstein differently, which he happily welcomed. The writer eventually
moved out of this party oasis, though he never married. As he himself once mused,
"I don't find that one town or one woman,
or one job or one career makes me happy. What makes me happy is changing all the time."
LeRoy Neiman and Playboy go hand in hand. His artwork was as beloved as his contemporary
Norman Rockwell. Yet als adored as he was, he lacked the respect of mainstream critics.
But he didn't much care about that. As Hugh Hefner once mused to Cigar Aficionado,
"He quite intentionally invented himself as a flamboyant artist, not unlike Salvador Dalí."
Neiman and Hefner met while working at a department store, with the future Playboy founder
serving as a copywriter and Neiman as a freelance fashion illustrator. When Hefner left to launch
his own magazine, he asked his friend to join. By the 1960s, his sports drawings in the men's
magazine were instantly recognizable. Neiman would eventually live on and off at the Playboy mansion.
He and Hefner worked together for over 50 years, and it seems like Neiman never had
a negative thing to say about his friend. As he once declared during an interview in 1999,
"[Hef's] a good person. I couldn't cite anything he ever did that was malicious to anybody."
Perhaps one of the biggest names — or several of the biggest names — to ever
stay at the Mansion was the iconic rock band the Rolling Stones. According to the book Rock Star:
The Making of Musical Icons from Elvis to Springsteen, the band shacked up in Hefner's
crib while they were touring in Chicago, which made for the perfect storm. Hef's excessive
lifestyle blended perfectly with the London lads, though it led to disastrous consequences.
In his biography Life, guitarist Keith Richards detailed a story of the time
that he and saxophonist Bobby Keys started a fire in one of the Mansion's bathrooms.
They'd snagged their tour doctor's bag for some drugs
in exchange for time with a Playmate. As they began indulging, they noticed smoke,
but they were too high to do anything about it. The fire alarm went off, causing employees
to rush in and put out the fire. Hefner moved his mansion to Los Angeles shortly after the incident.
James Caan will forever be remembered as the hotheaded Sonny Corleone in the 1972
gangster epic The Godfather. The New York City native went on to portray
even more mobsters on camera, and his explosive life off-camera was reportedly just as compelling.
When Caan wasn't acting, he fueled his life with testosterone-fueled behavior
and a lot of cocaine. In 1999, he told The Guardian that his, quote,
"destructive kick" in the 80s developed after his sister died of cancer. As he recalled,
"I was just angry, raging at the world. Getting high and partying seemed like the best option."
His partying antics are probably what attracted him to the Playboy Mansion,
where he lived for a brief period to recover from a breakup. As he admitted to The Guardian,
"There were tons of girls over there and well, I'm sorry, but I liked 'em."
Caan stayed at Hefner's abode for quite a while in the 70s,
but he eventually moved out. He once revealed,
"Hef didn't want me to leave because I guess I brought a lot of levity to the place."
Of course, the most obvious celebrities that have ever spent any time at the Playboy Mansion were
the Playmates themselves. One notable Playmate is Holly Madison, who was Hefner's main squeeze at
the Mansion for seven years. She originally had plans to get into show business, as she
studied theater at Portland State University and later Loyola Marymount in Los Angeles.
To pay for school, Madison worked at Hooters and modeled, which is how she met Hefner.
She eventually moved into the mansion, and along with fellow Playmate Kendra Wilkinson,
she starred on the E! reality series The Girls Next Door, which documented their lives in the
famous abode. Since then, both Madison and Wilkinson have released their own memoirs,
which are littered with scandalous stories of their time at Hef's crib.
Another Playmate of note is Detroit Rock City actor Shannon Tweed, who met Hefner in the 80s
after being scouted by Playboy photographers in Toronto. When he asked her to move in,
she did so and ended up dating him for approximately two years. Interestingly enough,
she has Hefner to thank for her first and only marriage to Kiss bassist Gene Simmons,
whom she met at the Mansion. She even invited Hefner to her wedding with the rocker.
Oscar-nominated actor Tony Curtis once called the Playboy Mansion his home in the 1980s. He moved in
as a means to escape his out-of-control lifestyle. The Bronx-born thespian started his career with
a contract with Universal Pictures in the 1940s thanks to his blue eyes and overall good looks. He
went on to star in iconic flicks like Some Like It Hot and Spartacus, among countless others.
Curtis' off-camera life was thriving in the 50s and 60s as well,
as he was romantically linked to such stars as Janet Leigh, Marilyn Monroe,
and Natalie Wood. But his thriving love life couldn't stop his alcohol and drug struggles,
and by 1982, he checked himself into rehab. As he told the Los Angeles Times in 1985, it was after
he left rehab that his friend Hugh Hefner invited him and his son Benjamin to live in the Playboy
Mansion. Multiple attractive women were now suddenly his roommates, but he made sure to note,
"We stay out of everyone's way. We keep pretty much to ourselves."
"What are you doing tonight?"
"Tonight?"
While Curtis eventually moved out,
he was still privy to some of the mansion's high-profile parties.
He rubbed elbows with fellow industry legends, like legendary critic Roger Ebert, who noted that
he spent some time with Curtis at the bar during the opening party of the Holmby Hills abode.
Hugh O'Brian will probably forever be remembered for his Emmy-nominated turn as the title character
in the Western TV show The Life and Legend of Wyatt Earp. His start in showbiz is interesting,
mainly because it wasn't what he initially wanted to do. In the late 1940s, O'Brian had his
heart set on becoming a lawyer. The woman he was dating at the time happened to be a stage actor,
so one evening when he came to see her at rehearsals, he discovered that the leading
man hadn't shown up. After reading the lines in his place, O'Brian was asked to take part in the
production permanently. And after glowing reviews, his career path was suddenly set.
O'Brian went on to appear in movies that starred such legends as Bruce Lee and John Wayne. Along
the way, he also became pals with Hugh Hefner. As Playboy illustrator LeRoy Neiman once told The New
York Times, O'Brian was, quote, "always there" during the mansion's heyday. He even spent five
months living in the pad's "red room," and some of the Playmates helped him tidy his room each day.
Linda Lovelace was once one of the biggest stars in the adult industry, having starred in the
legendary Deep Throat in 1972. But the story behind Lovelace's success is heartbreaking,
as it allegedly wasn't something she was genuinely interested in.
While in her early 20s, she married businessman Chuck Traynor as a means
to escape her abusive family life, but he then allegedly forced her into adult entertainment.
Lovelace first appeared in shorter 8mm adult films before Deep Throat was released and went
on to gross millions in box office receipts. But almost nothing went to its main star.
Nevertheless, the film made Lovelace a household name, and her celebrity status
meant that she was suddenly rubbing elbows with the elite in New York.
Her success naturally caught the attention of Hugh Hefner, which led to her living in the
Playboy Mansion for a period. While it's unknown exactly what happened during her time there,
she did reveal a disturbing story in her biography Ordeal, as she alleged that Hefner,
quote, "sodomized" her and tried to make her have intercourse with a dog. Lovelace
passed away in 2002 at the age of 53 after suffering injuries from an automobile accident.
If you or someone you know is dealing with domestic abuse,
you can call the National Domestic Violence Hotline at 1−800−799−7233.
You can also find more information, resources, and support on their website.