Superstars playing the Super Bowl is a relatively recent phenomenon. During the game’s first quarter century, the NFL was loathe to offend the public at large, so instead of pop phenomena, they’d anchor the halftime show with dance troupes and marching bands—or, in the case of a truly bizarre program from 1989, a magical Elvis Presley impersonator called Elvis Presto. Things started to change in 1993, when Michael Jackson headlined the Super Bowl Halftime Show at the Rose Bowl. Sure, New Kids on the Block appeared at halftime during in 1991, but Michael Jackson treated the game as an afterthought: he put a concert into the confines of the Super Bowl.
It took a while for the NFL to loosen up enough to let other artists follow Jackson’s lead. For the next 10 years, they made halting progress until there was a sea change in the early 2000s, a change that started with Aerosmith and NYSNC sharing the stage in 2001 and solidified with U2 commanding the stadium in 2002. From that point forward, it’s been nothing but superstars headlining the Halftime Show, a tradition that continued with Rihanna’s gravity-defying performance during Super Bowl LVII—but did those floating stages help her rise to the top of this list? Since it’s the 30th anniversary of Michael Jackson reinventing the rules for the Super Bowl Halftime Show, this is the perfect opportunity to take a look back at the highlights—as well as a few debacles—from the last three decades.