Kylie Jenner (& Travis Scott)
Kylie Jenner, you’re also doing amazing, sweetie!
The 22-year-old posed for Playboy‘s “Pleasure” issue in September 2019 with her 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.
Kim Kardashian West
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!”
At age 19 — during her wild child years — the actress donned the Playboy bunny.
A pre-Oscar Theron appeared on the cover in May 1999.
In 2012, Lohan recreated one of the original Playboy covers when she posed in the iconic bunny chair.
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.
The model was at the height of her career when she posed in December 1999.
Field wore the bunny costume for a 1986 cover.
Playboy published nude photos the Material Girl had shot with photographer Martin H.M. Schreiber.
The iconic actress posed for a 1966 issue — notably all covered up.
As The Hills took over MTV, Montag stripped down for Playboy.
Pressly posed for her second Playboy cover in 2004, just before she starred on My Name is Earl.
At age 40, the model and star of The Jamie Foxx Show went nude for the magazine.
Reid landed the cover of Playboy’s special anniversary issue in 2010.
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.
The Australian model channeled Brigitte Bardot for her 1994 cover.
The Baywatch star snagged the cover of Playboy’s 55th anniversary issue in 2009.
The superstar singer posed for a 2007 cover.
The model stripped down for three Playboy covers in the ’90s, with this one, in October 1998, being her last.
Moss put on the iconic bunny tail for the magazine’s 60th anniversary issue.
Hannah channeled her Splash days with this mermaid-like cover in 2003.
Dita Von Teese
The burlesque dancer posed for her first cover in 2002.
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.
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.
Monroe graced the first-ever cover of Playboy in 1953 when her star was on the rise.