Best: Stevie Wonder, 1999
Whoa, talk about a trip down memory lane. Stevie Wonder appeared at the 1999 Super Bowl halftime show with elegance and style in spades. He performed a number of hits and allowed Gloria Estefan to try her hand at redeeming herself at the event. He sang “Sir Duke” as a way to celebrate the hundredth birthday of Duke Ellington. She helped spice things up for the viewers in Miami with an up-tempo salsa percussion. Big Bad Voodoo Daddy also made an appearance. There were a lot of great moments from this performance, but we thought it was funny when Stevie Wonder cruised around the field in a car.