12. Prince's Butt Getts Cheeky (1991)
Prince's orgiastic demonstration of Diamonds and Pearls-era hit "Gett Off" lasted nearly seven minutes. Pity the VMAs viewer checking their watch for even a second as the funky pop icon illustrated 23 positions in a one-night-stand wearing a ventilated yellow suit that left nothing to the imagination. Even on a flame-filled, multi-tiered stage filled with musicians and writhing dancers, Prince's lithe movements and muscular guitar work remained the focus — especially once a few spins made it abundantly clear that his suit had holes in the seat to showcase his butt. "Let me show you, baby, I'm a talented boy," he sang.