Marilyn Monroe graced an early Playboy cover in December, 1963.
Appealing to a broader audience, Playboy featured folk singer, Joan Baez, on its July, 1970 cover.
Model, Jean Bell, was October, 1971's controversial cover star—the first African American woman to appear on a Playboy cover.
In October 1977, Playboy got deep with Barbra Streisand.
Heartthrob Farah Fawcett featured on Playboy's December, 1978 cover.
Model Christie Brinkley graces the November, '84 cover.
Suzanne Sommers revealed all in December, 1984.
Goldie Hawn's quintessentially 80's cover (January, 1985).
Unlike a virgin...Madonna, September 1985.
A fresh-faced Brooke Shields was the December 1986 cover star.
Playboy's fashion affair continues with model Cindy Crawford in July, 1988.
Supermodels were no strangers to Playboy Covers. Stephanie Seymour (February, 1993).
Elle Macpherson was the cover girl for May '94's bare cover.
Claudia Schiffer, another supermodel, on the May '97 cover.
Sensing a trend? A fashionable Naomi Campbell finds her way onto the Playboy cover in December, 1999.
Kim Kardashian smolders on the December 2007 cover.
Breakout British sensation Daisy Loewe models the cover of Playboy in September, 2011.
Playboy called upon Kate Moss for it's 60th anniversary issue in January, 2014.
Sarah McDaniels took Playboy into the digital age with Playboy's relaunch cover in March, 2016.
Camille Rowe teases on the April 2016 cover.
Watch: Photographers “Always Ask” Kate Moss to Take Her Clothes Off