The August 1989 cover featured not only a spread of the women of Wall Street, but also the infamous interview with Mike Tyson where he noted that "the best punch [he] ever threw was at Robin Givens."
The August 1992 cover saluted the "all-American housewife" with a playmate holding a fork over a simmering stove in an evening gown.
As one of the most famous Playmates of the year, Anna Nicole Smith graced the cover of the June 1993 issue in a spread that evoked her idol, Marilyn Monroe.
Looking every bit the all-American girl, the then "Home Improvement" star Pam Anderson graced one of many covers in cowboy boots and Daisy Dukes.
In a comedic take on the mag, the September 1996 issue featured a cool bunny with images of a shirtless Uma Thurman at the beach.
Cementing her celebrity status, burlesque dancer Dita Von Teese appeared on the December 2002 celebrity issue with the headline "The Return of Fetish."
To promote the film "The House Bunny," whose concept she created, actress Anna Faris appeared on the September 2008 cover of Playboy.
In a creative cover, the November 1988 issue of Playboy focused on sex in cinema, with a sexy Jessica Rabbit on the cover.
In an exlusive to Playboy, a 42-year-old Daryl Hannah appeared in a nude pictoral spread to promote "Kill Bill"
Taking Playboy into the television realm, Hugh Hefner's girlfriends and the stars of "The Girls Next Door," Hugh Hefner's girlfriends Bridget Marquart, Holly Madison and Kendra Wilkinson appeared in a Novemeber 2005 cover.
Kim Kardashian graced the December 2007 cover of Playboy and was dubbed "Hollyood's New Sex Star."