1993: Michael Jackson
According to For the Win, this was the King of Pop’s last amazing performance. He stood still for 90 seconds as 100,000 fans waved and screamed their hearts out. He opened the show with “Jam”, then “Billie Jean”, followed by “Black or White”, and closed with “Heal the World”. For the Win said, “It was the birth of the modern-day Super Bowl spectacle.” Michael Jackson passed away in 2009.

1993: Michael Jackson
1998: Boyz II Men
Although a Boyz II Men halftime show sounded promising, it ended up being underwhelming. For starters, they did not perform “End of the Road”, which the audience did not like. They were still in the peak of their career back then, so they made a tribute to Motown. There were many iconic guests such as The Four Tops, The Temptations, Martha Reeves, and Smokey Robinson as well. It was not a complete flop, but it is not exactly the best performance ever either.

1998: Boyz II Men