01of 26Heather Rae YoungHeather Rae Young Arrives the Playboy and True Blood 2012 Event.Frazer Harrison/GettyTheSelling Sunsetstar credits posing naked for a Playboy centerfold in 2010 as the launchpad for her career.Reflecting on the experience toThe Sunin 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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Heather Rae Young
Heather Rae Young Arrives the Playboy and True Blood 2012 Event.Frazer Harrison/Getty

TheSelling Sunsetstar credits posing naked for a Playboy centerfold in 2010 as the launchpad for her career.
Reflecting on the experience toThe Sunin 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.”
02of 26Kylie Jenner (& Travis Scott)Travis Scott and Kylie Jenner (right).Kylie Jenner/InstagramKylie Jenner, you’realsodoing amazing, sweetie!The then-22-year-oldposed forPlayboy’s “Pleasure” issuein September 2019 with her on-and-off boyfriend, Travis Scott, in tow.Jenner posted the first photo from her sexy shoot onInstagram. 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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Kylie Jenner (& Travis Scott)
Travis Scott and Kylie Jenner (right).Kylie Jenner/Instagram

Kylie Jenner, you’realsodoing amazing, sweetie!
The then-22-year-oldposed forPlayboy’s “Pleasure” issuein September 2019 with her on-and-off boyfriend, Travis Scott, in tow.
Jenner posted the first photo from her sexy shoot onInstagram. 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.
03of 26Kim KardashianKim Kardashian on Playboy Magazine.Two months after the debut ofKeeping Up with the Kardashians, Kardashian posed for the cover. The shoot was documented on the E! show, where momKris Jenner, on set with her daughter, uttered the now-iconic phrase, “You’re doing amazing sweetie!”
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Kim Kardashian
Kim Kardashian on Playboy Magazine.

Two months after the debut ofKeeping Up with the Kardashians, Kardashian posed for the cover. The shoot was documented on the E! show, where momKris Jenner, on set with her daughter, uttered the now-iconic phrase, “You’re doing amazing sweetie!”
04of 26Drew BarrymoreDrew Barrymore on Playboy Magazine.At age 19 — during her wild child years — the actress donned thePlayboybunny.
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Drew Barrymore
Drew Barrymore on Playboy Magazine.

At age 19 — during her wild child years — the actress donned thePlayboybunny.
05of 26Charlize TheronCharlize Theron on the cover of Playboy Magazine 1999.A pre-Oscar Theron appeared on the cover in May 1999.
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Charlize Theron
Charlize Theron on the cover of Playboy Magazine 1999.

A pre-Oscar Theron appeared on the cover in May 1999.
06of 26Lindsay LohanLindsay Lohan on the cover of Playboy Magazine 2012.In 2012, Lohan recreated one of the originalPlayboycovers when she posed in the iconic bunny chair.
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Lindsay Lohan
Lindsay Lohan on the cover of Playboy Magazine 2012.

In 2012, Lohan recreated one of the originalPlayboycovers when she posed in the iconic bunny chair.
07of 26Olivia MunnOlivia Munn on the cover of Playboy Magazine.Munn was on the brink of her big breakout roles inDate NightandIron Man 2when she donned a bikini for the magazine.
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Olivia Munn
Olivia Munn on the cover of Playboy Magazine.

Munn was on the brink of her big breakout roles inDate NightandIron Man 2when she donned a bikini for the magazine.
08of 26Naomi CampbellNaomi Campbell on cover of Playboy Magazine 1999.PlayboyThe model was at the height of her career when she posed in December 1999.
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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.
09of 26Sally FieldSally Field on the cover of Playboy Magazine 1986.Field wore the bunny costume for a 1986 cover.
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Sally Field
Sally Field on the cover of Playboy Magazine 1986.

Field wore the bunny costume for a 1986 cover.
10of 26MadonnaMadonna on the cover of Playboy Magazine.Playboypublished nude photos the Material Girl hadshot with photographer Martin H.M. Schreiber.
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Madonna
Madonna on the cover of Playboy Magazine.

Playboypublished nude photos the Material Girl hadshot with photographer Martin H.M. Schreiber.
11of 26Jane FondaJane Fonda on the cover of Playboy Magazine 1966.The iconic actress posed for a 1966 issue — notably all covered up.
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Jane Fonda
Jane Fonda on the cover of Playboy Magazine 1966.

The iconic actress posed for a 1966 issue — notably all covered up.
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Heidi Montag
Heidi Montag on the cover of Playboy Magazine.

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Jaime Pressly
Jaime Presley on the cover of Playboy Magazine 2004.

14of 26Garcelle BeauvaisGarcelle Beauvais on the cover of Playboy Magazine.PlayboyAt age 40, the model and star ofThe Jamie Foxx Showwent nude for the magazine.
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Garcelle Beauvais
Garcelle Beauvais on the cover of Playboy Magazine.Playboy

At age 40, the model and star ofThe Jamie Foxx Showwent nude for the magazine.
15of 26Tara ReidTara Reid on the cover of Playboy Magazine 2010.Reid landed the cover ofPlayboy’s special anniversary issue in 2010.
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Tara Reid
Tara Reid on the cover of Playboy Magazine 2010.

Reid landed the cover ofPlayboy’s special anniversary issue in 2010.
16of 26Farrah FawcettFarrah Fawcett on the cover of Playboy Magazine.Two years after her iconic poster debuted, Fawcett posed forPlayboybut declined to go fully nude. That happened 17 years later for her second cover.
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Farrah Fawcett
Farrah Fawcett on the cover of Playboy Magazine.

Two years after her iconic poster debuted, Fawcett posed forPlayboybut declined to go fully nude. That happened 17 years later for her second cover.
17of 26Elle MacPhersonElle MacPherson on the cover of Playboy Magazine 1994.The Australian model channeled Brigitte Bardot for her 1994 cover.
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Elle MacPherson
Elle MacPherson on the cover of Playboy Magazine 1994.

The Australian model channeled Brigitte Bardot for her 1994 cover.
18of 26Carmen ElectraCarmen Electra on the cover of Playboy Magazine 2009.TheBaywatchstar snagged the cover ofPlayboy’s 55th anniversary issue in 2009.
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Carmen Electra
Carmen Electra on the cover of Playboy Magazine 2009.

TheBaywatchstar snagged the cover ofPlayboy’s 55th anniversary issue in 2009.
19of 26Mariah CareyMariah Carey on the cover of Playboy Magazine 2007.PlayboyThe superstar singer posed for a 2007 cover.
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Mariah Carey
Mariah Carey on the cover of Playboy Magazine 2007.Playboy

The superstar singer posed for a 2007 cover.
20of 26Cindy CrawfordCindy Crawford on the cover of Playboy Magazine 1998.The model stripped down for threePlayboycovers in the ’90s, with this one, in October 1998, being her last.
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Cindy Crawford
Cindy Crawford on the cover of Playboy Magazine 1998.

The model stripped down for threePlayboycovers in the ’90s, with this one, in October 1998, being her last.
21of 26Kate MossKate Moss on the cover of Playboy Magazine 2014.PlayboyMoss put on the iconic bunny tail for the magazine’s 60th anniversary issue.
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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.
22of 26Daryl HannahDarryl Hannah on the cover of Playboy Magazine 2003.Hannah channeled herSplashdays with this mermaid-like cover in 2003.
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Daryl Hannah
Darryl Hannah on the cover of Playboy Magazine 2003.

Hannah channeled herSplashdays with this mermaid-like cover in 2003.
23of 26Dita Von TeeseDita Von Teese on the cover of Playboy Magazine 2002.The burlesque dancer posed for her first cover in 2002.
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Dita Von Teese
Dita Von Teese on the cover of Playboy Magazine 2002.

The burlesque dancer posed for her first cover in 2002.
24of 26Pamela AndersonPamela Anderson on the cover of Playboy Magazine 2016.PlayboyAnderson is the record holder for the mostPlayboycovers 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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Pamela Anderson
Pamela Anderson on the cover of Playboy Magazine 2016.Playboy

Anderson is the record holder for the mostPlayboycovers ever with 14 total. This one, in 2016, originally marked the last nude issue of the magazine, until they reverted back in 2017.
25of 26Charisma CarpenterCharisma Carpenter on the cover of Playboy Magazine 2004.PlayboyThe actress was at the top of her game when she posed forPlayboyin 2004, just after starring inBuffy the Vampire SlayerandAngel.
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Charisma Carpenter
Charisma Carpenter on the cover of Playboy Magazine 2004.Playboy

The actress was at the top of her game when she posed forPlayboyin 2004, just after starring inBuffy the Vampire SlayerandAngel.
26of 26Marilyn MonroeMarilyn Monroe on the cover of Playboy Magazine 1953.PlayboyMonroe graced the first-ever cover ofPlayboyin 1953 when her star was on the rise.
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Marilyn Monroe
Marilyn Monroe on the cover of Playboy Magazine 1953.Playboy

Monroe graced the first-ever cover ofPlayboyin 1953 when her star was on the rise.
source: people.com