September 1996: Uma Thurman
Playboy has always prided itself on being on the level that they are now. These girls know what the magazine is about, willingly pose for it, and are paid. That sets Playboy apart from other publications, except on occasions when they forget.
In a huge lapse in judgment, Playboy bought snaps taken of a topless Uma Thurman at the beach and ran them as a cover pictorial, even going so far as to revive the fuzzy Playboy mascot of the '60s and '70s to add a whiff of peeping-tom creepiness.
Thurman was never against nudity. Judging from her first movies, she's the kind of art lover who might have posed for the magazine sooner or later. But thanks to this issue, that "sooner or later" became more like never.