Best: In Living Color, Super Bowl XXVI
Technically it wasn't a Super Bowl halftime show. FOX didn't even have the rights to broadcast football - yet they took 25 million viewers away from the real deal with a brilliant In Living Color episode. Those who stayed with the Super Bowl were treated to Gloria Estefan and figure skaters. FOX didn't bother to pull a similar stunt the next year against Michael Jackson and they signed an NFL broadcasting deal a year later.