9 Musicians You Probably Forgot Were Playboy Cover Girls

5. Nancy Sinatra

Daughter of Ol' Blue Eyes, Nancy Sinatra probably didn't make her poppa too proud when she bared it all for Hefner's company in 1995. Most famous for her sexy singing on "These Boots Are Made For Walkin'," Sinatra waited another three decades to strip down for Playboy. Is 54-years-old too old to pose nude? Hell no. Especially when the middle-aged woman in question has clearly done a fair amount of walking in the interim and kept her bod in prime shape.