Issue: June 1994, July 1996, December 1996, September 1997, January 2005, July 2012

There are the women who appear in Playboy based on their achievements, and then there are the women who emerge from America to become girl-next-door sex symbols. Those are the Playmates. And every so often, a Playmate breaks through to the next level and becomes a celebrity.

Jenny McCarthy did it as well as anyone, going from a phenomenally popular Playmate pictorial to Playmate of the Year and then on to MTV's Singled Out. More than eye candy, she proved to be damn funny as well, going on to apear in BASEketball (1998) and Scary Movie 3 (2002). But she never turned her back on Playboy, returning to do her latest pictorial (and sixth cover) just last year at the age of 39.