Celebrities Who Once Lived At The Playboy Mansion

The Playboy empire that Hugh Hefner built was once nothing short of remarkable. Launching the magazine in 1953 with Marilyn Monroe in the centerfold, the publication rapidly began to be known as "a welcome antidote" in the stuffy '50s, with its inquisitive articles, and of course, nude pictures (via Biography). Immediately recognizable with its logo of a rabbit's head with a bow tie, Hef expanded his brand to include clubs, hotels, and of course, the Playboy mansion, which was initially located in Chicago, before moving to the Holmby Hills area of Los Angeles.

According to the Los Angeles Times, the '70s and '80s were the estate's heyday — as the article notes, "attending one of Hefner's parties at the Playboy mansion was a sign of status," with its notorious party scene attracting countless celebrities and A-listers. "It was such a lifestyle," Pamela Anderson once mused to the outlet. "Playboy Mansion was like my university. It was full of intellectuals, sex, rock 'n' roll, art, all the important stuff."

Sure enough, the mansion was filled with an eclectic revolving mix of characters, and considering the Gothic Tudor Revival–style estate had 29 rooms (via Architectural Digest), Hefner often welcomed various stars to live within his hedonistic palace for an extended period of time. Here are the celebrities who once lived at the Playboy mansion.

James Caan

James Caan will forever be remembered as the impulsive and incredibly violent Sonny Corleone in Francis Ford Coppola's 1972 gangster epic, "The Godfather." The New Yorker went on to portray even more mobsters on camera, and as The Guardian reveals, his explosive life off-camera was just as compelling to watch, too.

While Caan wasn't acting, he fueled his life with "testosterone-heavy extracurricular activities" and a lot of cocaine — he told the outlet that his "destructive kick" in the 1980s came to be after his sister died of cancer. "I was just angry, raging at the world," he mused, adding, "Getting high and partying seemed like the best option." His partying antics are probably what attracted him to the Playboy mansion, as well, where he lived for a brief period to recover from a breakup. "There were tons of girls over there and well, I'm sorry, but I liked 'em," the "Rollerball" actor told The Guardian.

While Caan stayed at Hugh Hefner's abode for quite a while in the 1970s, he eventually moved out. "Hef didn't want me to leave because I guess I brought a lot of levity to the place," the actor once mused (via The Telegraph). Dubbing the Playboy mansion the "greatest nightclub in the world," Caan revealed that he even contemplated suicide because he figured his life wasn't "getting any better than this."

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Shel Silverstein

It may seem hard to believe that a beloved children's author once lived within the bacchanalian walls of the Playboy mansion. That esteemed wordsmith was none other than "The Giving Tree" author Shel Silverstein. According to Ozy, Silverstein's college days seemed rather bleak before he served time in the Korean War; the outlet notes one school gave him the boot, while he decided to drop out from another. On top of that, the poet once mused that he "didn't get laid much" — although that would eventually change after he returned to America and landed a job as Playboy magazine's "cartoon-drawing foreign correspondent."

Once he moved back to Chicago (where the Playboy mansion was situated at the time), he became a part of Hugh Hefner's "inner circle," living in the home for an extended time (sometimes even months), entertaining the revolving door of various guests. As "A Boy Named Shel" notes, this fame also meant that women suddenly looked at Silverstein differently, too — an affection which he "welcomed." Perhaps it's where he sought inspiration for some of his most famous poems, as well; according to Ozy, even a brief skim of "Hug O' War" from "Where the Sidewalk Ends" suddenly takes an entirely different meaning.

Silverstein eventually moved out of Hefner's party oasis, yet he never married. As the poet 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" (via Playboy).

Tony Curtis

Academy Award nominee Tony Curtis once called the Playboy mansion his home in the 1980s — and he moved in there as a means to escape his out-of-control lifestyle. According to Biography, the Bronx-born actor started his career with a contract with Universal Pictures at the end of the 1940s thanks to his blue eyes and overall good looks, going on to star in now-iconic flicks such as "Some Like It Hot" and "Spartacus," among countless others.

Curtis' life off-camera was thriving in the '50s and '60s as well, and the star was linked to Hollywood beauties such as Janet Leigh (his first wife), Marilyn Monroe, and Natalie Wood. Yet even his thriving love life couldn't stop his alcohol and drug struggles, and by 1982, he checked himself into rehab (via Biography). As the actor told the Los Angeles Times in 1985, it's after he left rehab that his "generous and wonderful friend" Hugh Hefner invited him and his son, Benjamin, to live in the Playboy mansion while the actor tried "to sort out [his] life." Noting the attractive women that were suddenly his roommates, Curtis was quick to add, "we stay out of everyone's way. We keep pretty much to ourselves."

While the "Operation Petticoat" actor eventually moved out, he was still privy to some of the mansion's high-profile parties, rubbing elbows with fellow industry legends, such as Roger Ebert, who noted that he spent some time with Curtis "at the bar" during the opening party of the Holmby Hills abode. 

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

Jenny McCarthy

Former MTV host and "Dirty Love" actor Jenny McCarthy has Hugh Hefner to thank for her career. According to The New York Times, McCarthy came from humble beginnings, dreaming of the A-list since she was a young girl. After spending two years at university, McCarthy snagged a job in Chicago at a Polish grocery store, hoping to jump-start her modeling career on the side. After being "told she was too fat" by one agency, she left feeling dejected and spotted Hefner's Playboy building by chance. "Something drew me there," she told the outlet.

While speaking on her radio program "The Jenny McCarthy Show" after the magazine mogul's death in 2017, the Illinois-born star revealed [TIMESTAMP: 1:40] that after spotting the Playboy offices that day in 1993, she merely waltzed inside and asked what the steps would be to land an opportunity with the mag. Lo and behold, after taking some test shots, she went on to become Playboy's Miss October that very same year. [5:40] "Here I am today, and it's all because of this opportunity that Hef gave me," she fondly remembered.

Per The New York Times, McCarthy moved into the mansion shortly after her centerfold — although allegedly, Hef's heyday of partying was well behind him at that point. Unfortunately, after a few months, McCarthy saw herself moving out due to her hometown peers denouncing her career choice. "I had to move on. The highest you can do is Playmate of the Year. There is no Playmate of the Century," she explained.

Hugh O'Brian

Hugh O'Brian will perhaps forever be remembered for his Emmy-nominated role as the titular character in "The Life and Legend of Wyatt Earp," a six-season series that the Los Angeles Times notes is "TV's first adult western" of the '50s and '60s. O'Brian's start in the filmmaking business is interesting, mainly because it isn't even something he initially wanted to do.

According to the Los Angeles Times, in the late '40s, O'Brian had his heart set on becoming a lawyer, saving up cash to make his trek to Yale University from Los Angeles. The woman he was dating at the time just so happened to be a stage actor, so one evening, when he came to see her at rehearsals, the future star discovered that the leading man "didn't show up." After reading the lines in place of the actor, O'Brian was asked to take part in the production permanently. After glowing reviews, the actor's career path was suddenly decided.

Eventually, O'Brian became an A-list star, working with legends such as Bruce Lee and John Wayne. Along the way, he became pals with Hugh Hefner, and as Playboy illustrator LeRoy Neiman told The New York Times, in the Playboy mansion's heyday, O'Brian was "always there." He was there so often, in fact, that he even spent five months living in the "red room" of the pad, noting that some of the Playmates would "help [him] straighten [his] room every day" (via True West).

The Rolling Stones

Life at the Playboy mansion saw big-name celebrities come and go since its inception at the original Chicago location in 1959. But perhaps one of the biggest names to stay there was the Rolling Stones. According to "Rock Star: The Making of Musical Icons from Elvis to Springsteen," the legendary band shacked up in Hugh Hefner's crib while they were touring in Chicago, making for the perfect storm. As the book notes, "the excesses" of Hef's life blended perfectly with the London lads — to the point that it led to disastrous consequences.

In a hilarious retelling in his biography, "Life," guitarist Keith Richards detailed a story of the time he and saxophonist Bobby Keys "set fire to [a] bathroom" in the mansion. As the tale goes, the pair had snagged their tour doctor's bag for "free dibs" (aka drugs) in exchange for some time with a Playmate. As they began "smorgasboarding," they noticed smoke in the room – yet were too high to do anything about it. "It really was a delayed reaction," Richards mused. Of course, the fire alarm went off, causing employees to rush in and put the fire out. According to the Stone, Hefner moved his mansion to Los Angeles shortly after the incident.

While it's unclear if the band spent more time at the mansion on other occasions, Playboy illustrator LeRoy Neiman told The New York Times that frontman Mick Jagger "stayed there" at one point or another.

If you or anyone you know is struggling with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA's National Helpline at 1-800-662-HELP (4357).

LeRoy Neiman

LeRoy Neiman and Playboy magazine go hand in hand. According to The New York Times, at the height of his popularity, Neiman was one of America's "most popular artists," his work as beloved as other U.S. contemporaries such as Norman Rockwell. Interestingly enough, as adored as he was, he lacked the mainstream respect of critics who simply brushed his work aside. Nevertheless, Neiman didn't care. "He quite intentionally invented himself as a flamboyant artist, not unlike Salvador Dalí," mused his longtime friend, Hugh Hefner, to Cigar Aficionado in the '90s.

As revealed by the Los Angeles Times, Neiman and Hefner met while working at a department store, with the future Playboy founder snagging a job as a copywriter while Neiman worked as a freelance fashion illustrator. When Hef left to launch his own magazine, he asked his friend to join. By the '60s, his sports drawings in the men's magazine were instantly recognizable (via The New Yorker).

By the time Hef created his Playboy mansion in Chicago, Neiman would live there on and off. According to The New York Times, he was present to watch various A-listers move in and out, noting that "it was nothing" to run into a famous face during breakfast at the pad. Neiman and Hefner worked together for over 50 years, and it seems like Neiman never had a negative thing to say. As he once revealed in an interview in 1999, "[Hef's] a good person. I couldn't cite anything he ever did that was malicious to anybody."

Linda Lovelace

Linda Lovelace was once one of the biggest stars of the adult industry, having starred in "the first full-length pornographic film, 'Deep Throat'" (via Biography). The story behind Lovelace's success, however, is heartbreaking, as it allegedly wasn't something she was interested in. As it turns out, the star married Chuck Traynor in her early 20s as a means to escape her abusive family life, and it was her husband who "forced" her into pornography.

According to The Wall Street Journal, Lovelace first started in shorter 8mm adult films, until "Deep Throat" came out in 1972. While the production cost of the flick was low ($25,000, according to Biography), it grossed a whopping $600 million, yet sadly, almost nothing went to its main star. Nevertheless, "Deep Throat" made Lovelace a household name (regardless of the fact that it was "banned in most countries," per the Evening Standard), and her celebrity status meant she was suddenly rubbing elbows with the elite in New York.

Lovelace's success, of course, caught the attention of Playboy founder Hugh Hefner, as well. In fact, as revealed by the Evening Standard, this resulted in Lovelace living in the Playboy mansion for a period, as well. While it's unknown exactly what happened during her time at the mansion, the actor did reveal a disturbing story in her biography "Ordeal" (via Vice), where she alleged that Hefner "sodomized her and attempted to make her have sex with a dog."

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.

Elvis Presley

While it's unclear if Elvis Presley actually lived at the Playboy mansion, the King of Rock 'n' Roll was probably a visitor. As revealed by "Storms Never Last: Memoirs of a Playboy Bunny," sometime in the 1970s, the crooner allegedly took off his blue suede shoes for a night of debauchery with eight Playmates. This happened in a room that's since been dubbed the "Elvis Suite" — and it was never open to the public. In fact, as the book alleges, there have been plenty of A-listers who have requested to stay in the infamous room, yet it remained "off-limits to everyone except Hef."

It's easy to imagine Elvis spending time at the Playboy mansion as a recurring visitor; after all, the Holmby Hills location was one of Los Angeles' "most famous house[s]" for star-studded hedonist fun, as noted by the Los Angeles Times.

That being said, Holly Madison, one of Hef's former Playmates, denies there ever being a room for Presley. As she revealed in a 2021 TikTok, "there was no Elvis room," noting that she's heard Hefner himself tell people that the King was never even at the Playboy mansion. As of this writing, the jury's still out.

The Playmates

Of course, the most obvious celebrities that spent time at the Playboy mansion were the Playmates themselves — and some of them even found their own fame outside of Hugh Hefner's Gothic Tudor estate walls.

The first Playmate of note is Holly Madison, Hef's main squeeze at the mansion for seven years (via People). Madison originally had plans to get into the acting business, studying theater at Portland State University and later Loyola Marymount University in Los Angeles. To pay for her schooling, 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, starred in the E! Series, "The Girls Next Door," which documented their lives in the mansion. Since then, both Madison and Wilkinson have released their own memoirs after moving out, littered with scandalous stories of their time at Hef's crib (via People).

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 (via 650 CKOM). When the publishing legend asked her to move in, Tweed complied and dated him for approximately two years. In fact, the model has Hefner to thank for her first and only marriage to KISS bassist Gene Simmons, whom she met at the Playboy mansion. As Tweed has revealed in the past, "Simmons and Hefner had much in common" and even invited her former flame to her wedding with the rocker.