2. "Sooner or Later," The 63rd Academy Awards (1991)
Perhaps a surprising entry on this list is Madonna's performance of the Oscar-winning song "Sooner or Later" on the 1991 Academy Awards. The tune is from her 1990 film "Dick Tracy," which won composer Stephen Sondheim the Oscar for best original song. Often noted by fans as one of her best vocal performances, Madonna was in full-Marilyn Monroe mode here, vamping and va-va-vooming her way through the belty number.
1. "Express Yourself," MTV Video Music Awards (1989)
Where to begin? The light-up stairs! The bustiers! The running-man! The crotch-grab! With only two backing dancer/singers (longtime cohorts Niki Haris and Donna De Lory), Madonna showed that you didn't need pyrotechnics and an armada of dancers to heat up a TV stage. (Watch for the 4:15 mark, where Madonna gives us our first taste of her vogueing -- months before she released her smash single "Vogue.")