Fail Occurred: 6/1991

It's common knowledge that women don't buy Playgirl magazine. In 1991, Big Daddy Kane was approached to pose for Playboy's gay cousin. What followed were pages and pages of Big Daddy Kane doing an impersonation of the "Dick in the Box" video, fifteen years before there was a "Dick in the Box" video: John Lennon glasses, flat-top hair, and beige suits. (Big Daddy's cane was hidden from the cameras by silk boxers and bite-sized chocolate candies.) His come-hither bedroom eyes? Not a good look.