Any fans of KUWTK will remember the early episode when Kris Jenner scored a Playboy cover shoot for her daughter, Kim Kardashian. Kardashian was unsure about posing for the magazine due to her sex tape scandal earlier that year. She went for it, and more than a decade later it's clear that it wasn't a mistake!

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Kylie Jenner - Kylie Jenner and Travis Scott were in a high-profile relationship between 2017 and 2020. Jenner followed in her sister's footsteps and posed for Playboy in 2019, but with an interesting twist: Scott was the creative director of her photo shoot. Jenner said she agreed because she trusted him and trusted his vision.

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Drew Barrymore -

Drew Barrymore posed for Playboy in 1995 when she was just 19 years old. She had a father-daughter style relationship with Steven Spielberg after starring in 'E.T.' (1982) at the age of six. Spielberg made it clear he didn't approve, so Barrymore sent him an "apology" gift including three photos of her dressed as a nun with the messages "I'm sorry" and "I've seen the light."

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Madonna -

Madonna has always embraced her body and her sexuality. She appeared on the cover of Playboy in 1985 at the very beginning of her career. She was fully clothed on the cover photo, but wasn't afraid to show a lot more inside the magazine!

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Mariah Carey -

Mariah Carey posed for Playboy in 2006. She was promoting her tour The Emancipation of Mimi at the time. She didn't bare all, but rather rocked a gorgeous cut-out swimsuit for the cover.

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Marilyn Monroe -

Marilyn Monroe was the first ever Playboy cover star back in 1953. Hugh Hefner launched the magazine with US$8,000 and a few pictures of Monroe.

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Jessica Alba -

Jessica Alba was one of many women whose photos Hefner used in Playboy without their consent. Playboy reportedly used unethical means to procure a photo of Alba in a bikini from Columbia Pictures after she refused to pose for them.

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Paris Hilton -

Paris Hilton was often seen cozying up to Hugh Hefner at parties in the early 2000s, but surprisingly Playboy went ahead and used her photos for a 2005 issue without her permission. They used some older photos of her in a transparent t-shirt, which they already owned the rights to.

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Pamela Anderson -

Pamela Anderson was a Playboy regular for decades. She first posed for the magazine in 1989, shortly after being "discovered" at a football game. Over the years, she was featured on the cover more than 14 times. She was the final model to appear nude in the magazine, before they announced their decision not to feature nude models anymore in 2016.

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Naomi Campbell -

Supermodel extraordinaire Naomi Campbell posed for Playboy in 1999. Not only did she get the cover, she also had a 14-page spread inside the magazine! It was both stylish and sexy.

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Charlize Theron -

Charlize Theron is another actress who had her photos used in Playboy without her permission. Theron had done an intimate photo shoot when she was still an aspiring actress and model. Playboy managed to procure the photos and used them without her consent. She tried to sue and have the magazines taken out of circulation, but failed.

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Dolly Parton -

The incomparable Dolly Parton graced the cover of Playboy wearing bunny ears in 1978. She was promoting her album 'Heartbreaker' and, no, she did not take it all off!

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Lindsay Lohan -

Lindsay Lohan appeared on the cover of Playboy in 2012. She wore nothing, but sat on a red chair shaped like a Playboy bunny that strategically covered her body.

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Dita Von Teese -

World-famous burlesque performer Dita Von Teese is more alternative than most of the Playboy cover girls, but a perfect choice nonetheless! She was extremely proud when she appeared on the cover in 2002, and years later told Elle, "I think it's sad that that kind of photography might go away."

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Kate Moss -

Kate Moss went full bunny for a Playboy cover in 2013. She was chosen as the feature model for the 60th anniversary edition of the magazine.

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Barbra Streisand -

This ones is a surprise, but Barbra Streisand was a Playboy cover girl in 1977. The photos were tasteful, fun, and oh-so '70s.

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Cindy Crawford -

Cindy Crawford appeared on the cover of Playboy in 1988, and then again in 1998. Years later, she told Net-a-Porter that she had no regrets about posing nude.

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Anna Faris -

Anna Faris starred in the 2008 comedy 'The House Bunny.' She played a Playboy Bunny who joins a sorority of awkward girls to teach them about men. Faris appeared on the cover of Playboy to promote the movie, but she kept it pretty PG.

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Azealia Banks -

Azealia Banks' 2013 Playboy cover was fun and vibrant. She got a little raunchier for the rest of the photos, where she posed completely nude in a paddling pool pouring milk all over herself.

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Geri Halliwell -

Geri Halliwell had taken some risqué photos prior to her career as a Spice Girl. They surfaced in Playboy without her consent when she became famous.

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Kim Basinger -

The gorgeous Kim Basinger shot her Playboy cover in 1981, but it wasn't released until 1983. That was the year she appeared in the James Bond film 'Never Say Never.' Playboy cover girl and Bond girl in one year–wow!

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Chelsea Handler -

Comedian and TV personality Chelsea Handler surprised fans with her Playboy appearance in 2010. The cover photo was revealed on an episode of 'The Tonight Show with Jay Leno.'

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Sharon Stone -

Sharon Stone was already a major sex symbol of the '80s and '90s. She appeared on the cover of Playboy in 1990 to promote the movie 'Total Recall.'

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Raquel Welch -

Actress Raquel Welch landed the Playboy cover in 1979. She wore an incredible red swimsuit that would rival the 'Baywatch' ensemble.

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Elle Macpherson -

Elle Macpherson was nicknamed "The Body" during the height of her career, and it's easy to see why. She reportedly told the Playboy photographer that she would go nude, but only on her own terms.

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Carmen Electra -

Carmen Electra was a Playboy regular and deemed by many the sexiest bunny of all time. She appeared on the cover three times, and it helped launch her career as a mainstream model.

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Goldie Hawn -

The wonderful Goldie Hawn appeared on the holiday edition of Playboy in 1985. She posed sitting in a giant Champagne glass wearing a white shirt and red heels.

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Anna Nicole Smith -

Anna Nicole Smith lived a short but exciting life, appearing on the cover of Playboy five times. She was named Playmate of the Year in 1993.

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Joan Collins -

Joan Collins did the cover of Playboy in 1983, and she went full 'Dynasty' glam. She was already 50 years old at the time, and she looked amazing!

Sources: (Glamour) (Marie Claire) (Screen Rant) (People)

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Kim Kardashian -

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Drew Barrymore -

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Madonna -

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Mariah Carey -

Mariah Carey posed for Playboy in 2006. She was promoting her tour The Emancipation of Mimi at the time. She didn't bare all, but rather rocked a gorgeous cut-out swimsuit for the cover.

Getty Images

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Marilyn Monroe -

Marilyn Monroe was the first ever Playboy cover star back in 1953. Hugh Hefner launched the magazine with US$8,000 and a few pictures of Monroe.

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Jessica Alba -

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Paris Hilton -

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Pamela Anderson -

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Naomi Campbell -

Supermodel extraordinaire Naomi Campbell posed for Playboy in 1999. Not only did she get the cover, she also had a 14-page spread inside the magazine! It was both stylish and sexy.

Getty Images

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Charlize Theron -

Getty Images

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Dolly Parton -

The incomparable Dolly Parton graced the cover of Playboy wearing bunny ears in 1978. She was promoting her album 'Heartbreaker' and, no, she did not take it all off!

Getty Images

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Lindsay Lohan -

Lindsay Lohan appeared on the cover of Playboy in 2012. She wore nothing, but sat on a red chair shaped like a Playboy bunny that strategically covered her body.

Getty Images

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Dita Von Teese -

Getty Images

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Kate Moss -

Kate Moss went full bunny for a Playboy cover in 2013. She was chosen as the feature model for the 60th anniversary edition of the magazine.

Getty Images

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Barbra Streisand -

This ones is a surprise, but Barbra Streisand was a Playboy cover girl in 1977. The photos were tasteful, fun, and oh-so '70s.

Getty Images

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Cindy Crawford -

Cindy Crawford appeared on the cover of Playboy in 1988, and then again in 1998. Years later, she told Net-a-Porter that she had no regrets about posing nude.

Getty Images

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Anna Faris -

Getty Images

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Azealia Banks -

Azealia Banks' 2013 Playboy cover was fun and vibrant. She got a little raunchier for the rest of the photos, where she posed completely nude in a paddling pool pouring milk all over herself.

Getty Images

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Geri Halliwell -

Geri Halliwell had taken some risqué photos prior to her career as a Spice Girl. They surfaced in Playboy without her consent when she became famous.

Getty Images

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Kim Basinger -

Getty Images

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Chelsea Handler -

Comedian and TV personality Chelsea Handler surprised fans with her Playboy appearance in 2010. The cover photo was revealed on an episode of 'The Tonight Show with Jay Leno.'

Getty Images

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Sharon Stone -

Sharon Stone was already a major sex symbol of the '80s and '90s. She appeared on the cover of Playboy in 1990 to promote the movie 'Total Recall.'

Getty Images

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Raquel Welch -

Actress Raquel Welch landed the Playboy cover in 1979. She wore an incredible red swimsuit that would rival the 'Baywatch' ensemble.

Getty Images

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Elle Macpherson -

Elle Macpherson was nicknamed "The Body" during the height of her career, and it's easy to see why. She reportedly told the Playboy photographer that she would go nude, but only on her own terms.

Getty Images

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Carmen Electra -

Carmen Electra was a Playboy regular and deemed by many the sexiest bunny of all time. She appeared on the cover three times, and it helped launch her career as a mainstream model.

Getty Images

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Goldie Hawn -

The wonderful Goldie Hawn appeared on the holiday edition of Playboy in 1985. She posed sitting in a giant Champagne glass wearing a white shirt and red heels.

Getty Images

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Anna Nicole Smith -

Anna Nicole Smith lived a short but exciting life, appearing on the cover of Playboy five times. She was named Playmate of the Year in 1993.

Getty Images

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Joan Collins -

Joan Collins did the cover of Playboy in 1983, and she went full 'Dynasty' glam. She was already 50 years old at the time, and she looked amazing!

Sources: (Glamour) (Marie Claire) (Screen Rant) (People)

Getty Images

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Famous women who posed for Playboy

Some of these cover stars will surprise you!

12/05/21 | StarsInsider

CELEBRITY Photo shoots

Depending on your perspective, you might see Playboy magazine as a sleazy rag or a part of history that has gained prestige over the years. It has played a major role in pop culture for decades, and while it's not the most feminist publication, many woman have aspired to appear on its cover. Regardless of its perception, many powerful female icons have graced its pages, from Barbra Streisand to Madonna. Some revealed a lot more than others, others didn't even voluntarily appear in the magazine, but all made an impression.

Click through this gallery to see which famous and successful women have posed for Playboy over the years.