9. Madonna (1989)
The VMAs have always been a place for Madonna to flex her visual savvy, often meaning a performance both iconic and distinct from the aesthetic of her hit videos. In 1989, however, she opened the broadcast by bringing a scaled down version of David Fincher's Fritz Lang fever dream in "Express Yourself." Wearing a lace bustier temporarily concealed by a baggy suit jacket, Madge descends a staircase, the steps lighting up as she touches them, "Billie Jean"-style. Years before Michael Jackson created controversy with the "Black or White" video, she grabbed her crotch while the microphone was held in place by her cleavage.