8. Madonna (1993)
Before there was Jo Calderone, there was Madonna's gender-bending performance of "Bye Bye Baby," the singer donning a tailcoat and top hat in a burlesque/bordello setting that previewed Madonna's 1993 Girlie Show World Tour, which would kick off in a few weeks. In retrospect, the song selection is strange — "Bye Bye Baby" wasn't even released as a single in the States. But Madonna's VMAs portfolio is stacked with captivating presentations, and the risqué "Bye Bye Baby" performance (full of stroked inner-thighs, spanks, frottage, etc.) was another visual stunner.