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.

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).

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.

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.

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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."

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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.