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  3. Heather Rae Young, Kim Kardashian, Drew Barrymore and 23 More Celebrities Who Posed for Playboy

Heather Rae Young, Kim Kardashian, Drew Barrymore and 23 More Celebrities Who Posed for Playboy

Find out which celebrities have posed for Playboy since its 1953 launch

J.Mazziotta2334
By Julie Mazziotta Updated November 30, 2021 03:13 PM
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Heather Rae Young

SAN DIEGO, CA - JULY 14: Heather Rae Young attends the Playboy and True Blood 2012 Event on July 14, 2012 in San Diego, California. (Photo by Frazer Harrison/Getty Images For Playboy)
Credit: Frazer Harrison/Getty

The Selling Sunset star credits posing naked for a Playboy centerfold in 2010 as the launchpad for her career. 

Reflecting on the experience to The Sun in November 2021, she said: "It catapulted my career, it changed my life, it was the most defining moment in my life."

She added, "I don't regret anything I've ever done. I'm proud of my life. Everything I've done has got me to where I am today."

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Kylie Jenner (& Travis Scott) 

Kylie Jenner Travis Scott
Credit: Kylie Jenner/Instagram

Kylie Jenner, you're also doing amazing, sweetie!

The then-22-year-old posed for Playboy's "Pleasure" issue in September 2019 with her on-and-off boyfriend, Travis Scott, in tow.

Jenner posted the first photo from her sexy shoot on Instagram. In the snap, Jenner, wearing nothing but a cowboy hat, her butt partially exposed, embraces Scott. For his part, the rapper is shirtless, wearing only a pair of jeans with his diamond necklace and watch.

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Kim Kardashian West

Hugh Hefner 1926-2017 Playboy Magazine Founder

Two months after the debut of Keeping Up with the Kardashians, Kardashian West posed for the cover. The shoot was documented on the E! show, where mom Kris Jenner, on set with her daughter, uttered the now-iconic phrase, "You're doing amazing sweetie!"

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Drew Barrymore

Playboy magazine drops nudity

At age 19 — during her wild child years — the actress donned the Playboy bunny.

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Charlize Theron

charlize-theron

A pre-Oscar Theron appeared on the cover in May 1999.

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Lindsay Lohan

1B795CFD

In 2012, Lohan recreated one of the original Playboy covers when she posed in the iconic bunny chair.

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Olivia Munn

olivia-munn

Munn was on the brink of her big breakout roles in Date Night and Iron Man 2 when she donned a bikini for the magazine.

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Naomi Campbell

Playboy
Credit: Playboy

The model was at the height of her career when she posed in December 1999.

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Sally Field

sally-field

Field wore the bunny costume for a 1986 cover.

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Madonna

madonna

Playboy published nude photos the Material Girl had shot with photographer Martin H.M. Schreiber.

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Jane Fonda

jane-fonda

The iconic actress posed for a 1966 issue — notably all covered up.

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Heidi Montag

heidi-montag

As The Hills took over MTV, Montag stripped down for Playboy.

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Jaime Pressly

jaime-presley

Pressly posed for her second Playboy cover in 2004, just before she starred on My Name is Earl.

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Garcelle Beauvais

Playboy
Credit: Playboy

At age 40, the model and star of The Jamie Foxx Show went nude for the magazine.

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Tara Reid

tara-reid

Reid landed the cover of Playboy's special anniversary issue in 2010.

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Farrah Fawcett

farrah-fawcet

Two years after her iconic poster debuted, Fawcett posed for Playboy but declined to go fully nude. That happened 17 years later for her second cover.

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Elle MacPherson

elle-macpherson

The Australian model channeled Brigitte Bardot for her 1994 cover.

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Carmen Electra

carmen-electra

The Baywatch star snagged the cover of Playboy's 55th anniversary issue in 2009.

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Mariah Carey

Playboy
Credit: Playboy

The superstar singer posed for a 2007 cover.

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Cindy Crawford

cindy-crawford

The model stripped down for three Playboy covers in the '90s, with this one, in October 1998, being her last.

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Kate Moss

2014 Jan_Feb Cover_60th Anniv. Kate MossPlayboy
Credit: Playboy

Moss put on the iconic bunny tail for the magazine's 60th anniversary issue.

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Daryl Hannah

darryl-hannah

Hannah channeled her Splash days with this mermaid-like cover in 2003.

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Dita Von Teese

dita-von-teese

The burlesque dancer posed for her first cover in 2002.

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Pamela Anderson

2016 Jan_Feb Cover Pamela AndersonPlayboy
Credit: Playboy

Anderson is the record holder for the most Playboy covers ever with 14 total. This one, in 2016, originally marked the last nude issue of the magazine, until they reverted back in 2017.

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Charisma Carpenter

Playboy
Credit: Playboy

The actress was at the top of her game when she posed for Playboy in 2004, just after starring in Buffy the Vampire Slayer and Angel.

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Marilyn Monroe

1953 Dec Cover_Marilyn MonroePlayboy
Credit: Playboy

Monroe graced the first-ever cover of Playboy in 1953 when her star was on the rise.

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  • By Julie Mazziotta @julie_mazziotta

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    Everything in This Slideshow

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    1 of 26 Heather Rae Young
    2 of 26 Kylie Jenner (& Travis Scott) 
    3 of 26 Kim Kardashian West
    4 of 26 Drew Barrymore
    5 of 26 Charlize Theron
    6 of 26 Lindsay Lohan
    7 of 26 Olivia Munn
    8 of 26 Naomi Campbell
    9 of 26 Sally Field
    10 of 26 Madonna
    11 of 26 Jane Fonda
    12 of 26 Heidi Montag
    13 of 26 Jaime Pressly
    14 of 26 Garcelle Beauvais
    15 of 26 Tara Reid
    16 of 26 Farrah Fawcett
    17 of 26 Elle MacPherson
    18 of 26 Carmen Electra
    19 of 26 Mariah Carey
    20 of 26 Cindy Crawford
    21 of 26 Kate Moss
    22 of 26 Daryl Hannah
    23 of 26 Dita Von Teese
    24 of 26 Pamela Anderson
    25 of 26 Charisma Carpenter
    26 of 26 Marilyn Monroe

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    Heather Rae Young, Kim Kardashian, Drew Barrymore and 23 More Celebrities Who Posed for Playboy
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