6. Madonna - "Vogue" (1990)
Madonna made her name at the original VMAs in 1984, and six years later she came back determined to top herself. This time, she swapped in a Marie Antoinette ensemble for a wedding dress and she transformed the stage into an 18th century French castle. It was the culmination of a big night for Madonna since she was nominated for nine awards, though she lost most of the big ones to M.C. Hammer and Sinead O'Connor. Needless to say, she won the long game.