19. Madonna feat. Lenny Kravitz (1998)
In the late Nineties Madonna began expanding her on-record religious interests beyond Catholicism, and 1998 album Ray of Light honored them explicitly — particularly "Shanti/Ashtangi," a Hindu prayer paired with a William Orbit beat. Clad in a black dress and her hair ironed flat, Madonna performed part of that track to open the 1998 VMAs on a more subdued-than-usual note. But things soon got frantic: The dress was quickly dispensed with (in favor of a tank top) and she broke into Ray's brightly curious title track accompanied by Lenny Kravitz and an array of flipping and breaking dancers.