For many icons, from Madonna to Naomi Campbell, a Playboy cover is a rite of passage. The photos are visceral, tantalizing, and for many celebrities, incredibly empowering. Marilyn Monroe kicked off the trend in 1953 as the first-ever Playboy cover star, and dozens of icons since have adorned the cover of the magazine, now a byword for unapologetic sexiness. If you forgot about the icon covers from Kim Kardashian, Anna Faris, Brooke Shields, and more, well—we’re here to remind you. Let’s take a trip down memory lane, shall we?
Marilyn Monroe, December 1953
Jayne Mansfield, June 1963
Raquel Welch, December 1979
Steve Martin, January 1980
Bo Derek, March 1980
Kim Basinger, February 1983
Joan Collins, December 1983
Goldie Hawn, January 1985
Madonna, September 1985
Brooke Shields, December 1986
Cindy Crawford, July 1988
La Toya Jackson, March 1989
Sharon Stone, July 1990
Elle Macpherson, May 1994
Pamela Anderson, November 1994
Drew Barrymore, January 1995
Farrah Fawcett, December 1995
Geri Halliwell, May 1998
Charlize Theron, May 1999
Naomi Campbell, December 1999
Dita Von Teese, December 2002
Jaime Pressly, February 2004
Denise Richards, December 2004
Paris Hilton, March 2005
Mariah Carey, March 2007
Kim Kardashian, December 2007
Anna Faris, September 2008
Carmen Electra, January 2009
Olivia Munn, July August 2009
Lindsay Lohan, January February 2012
Kate Moss, February 2014
Azealia Banks, April 2015
Kylie Jenner, September 2019
From Marie Claire US
