Lifestyle Style 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 By Julie Mazziotta Julie Mazziotta Twitter Julie Mazziotta is the Sports Editor at PEOPLE, covering everything from the NFL to tennis to Simone Biles and Tom Brady. She was previously an Associate Editor for the Health vertical for six years, and prior to joining PEOPLE worked at Health Magazine. When not covering professional athletes, Julie spends her time as a (very) amateur athlete, training for marathons, long bike trips and hikes. People Editorial Guidelines Updated on November 30, 2021 03:13 PM Share Tweet Pin Email Trending Videos 01 of 26 Heather Rae Young Heather Rae Young Arrives the Playboy and True Blood 2012 Event. 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." 02 of 26 Kylie Jenner (& Travis Scott) Travis Scott and Kylie Jenner (right). 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. 03 of 26 Kim Kardashian Kim Kardashian on Playboy Magazine. Two months after the debut of Keeping Up with the Kardashians, Kardashian 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!" 04 of 26 Drew Barrymore Drew Barrymore on Playboy Magazine. At age 19 — during her wild child years — the actress donned the Playboy bunny. 05 of 26 Charlize Theron Charlize Theron on the cover of Playboy Magazine 1999. A pre-Oscar Theron appeared on the cover in May 1999. 06 of 26 Lindsay Lohan Lindsay Lohan on the cover of Playboy Magazine 2012. In 2012, Lohan recreated one of the original Playboy covers when she posed in the iconic bunny chair. 07 of 26 Olivia Munn Olivia Munn on the cover of Playboy Magazine. 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. 08 of 26 Naomi Campbell Naomi Campbell on cover of Playboy Magazine 1999. Playboy The model was at the height of her career when she posed in December 1999. 09 of 26 Sally Field Sally Field on the cover of Playboy Magazine 1986. Field wore the bunny costume for a 1986 cover. 10 of 26 Madonna Madonna on the cover of Playboy Magazine. Playboy published nude photos the Material Girl had shot with photographer Martin H.M. Schreiber. 11 of 26 Jane Fonda Jane Fonda on the cover of Playboy Magazine 1966. The iconic actress posed for a 1966 issue — notably all covered up. 12 of 26 Heidi Montag Heidi Montag on the cover of Playboy Magazine. As The Hills took over MTV, Montag stripped down for Playboy. 13 of 26 Jaime Pressly Jaime Presley on the cover of Playboy Magazine 2004. Pressly posed for her second Playboy cover in 2004, just before she starred on My Name is Earl. 14 of 26 Garcelle Beauvais Garcelle Beauvais on the cover of Playboy Magazine. Playboy At age 40, the model and star of The Jamie Foxx Show went nude for the magazine. 15 of 26 Tara Reid Tara Reid on the cover of Playboy Magazine 2010. Reid landed the cover of Playboy's special anniversary issue in 2010. 16 of 26 Farrah Fawcett Farrah Fawcett on the cover of Playboy Magazine. 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. 17 of 26 Elle MacPherson Elle MacPherson on the cover of Playboy Magazine 1994. The Australian model channeled Brigitte Bardot for her 1994 cover. 18 of 26 Carmen Electra Carmen Electra on the cover of Playboy Magazine 2009. The Baywatch star snagged the cover of Playboy's 55th anniversary issue in 2009. 19 of 26 Mariah Carey Mariah Carey on the cover of Playboy Magazine 2007. Playboy The superstar singer posed for a 2007 cover. 20 of 26 Cindy Crawford Cindy Crawford on the cover of Playboy Magazine 1998. The model stripped down for three Playboy covers in the '90s, with this one, in October 1998, being her last. 21 of 26 Kate Moss Kate Moss on the cover of Playboy Magazine 2014. Playboy Moss put on the iconic bunny tail for the magazine's 60th anniversary issue. 22 of 26 Daryl Hannah Darryl Hannah on the cover of Playboy Magazine 2003. Hannah channeled her Splash days with this mermaid-like cover in 2003. 23 of 26 Dita Von Teese Dita Von Teese on the cover of Playboy Magazine 2002. The burlesque dancer posed for her first cover in 2002. 24 of 26 Pamela Anderson Pamela Anderson on the cover of Playboy Magazine 2016. 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. 25 of 26 Charisma Carpenter Charisma Carpenter on the cover of Playboy Magazine 2004. 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. 26 of 26 Marilyn Monroe Marilyn Monroe on the cover of Playboy Magazine 1953. Playboy Monroe graced the first-ever cover of Playboy in 1953 when her star was on the rise.