Most Memorable Super Bowl Halftimes, 1990s – 2010s

Posted on December 22, 2021 - Last Updated on January 13, 2022

Before 1970, Super Bowl halftime shows starred marching bands, plus a little extra. In fact, the first Super Bowl halftime show featured two marching bands, a 200-person chorus, 300 pigeons, 10,000 balloons, and a pair of jet-pack flying men representing the competing leagues landing for a 50-yard line handshake.

After 1970, marching bands thinned out and popular entertainment stole the show. Some shows have been controversial and some funny — intentional or otherwise. One was laced with tragedy, and some have been great. And the exposure doesn’t hurt the performers, either. 

In this article, we highlight some of the most memorable halftime shows in Super Bowl history.

Michael Jackson, Super Bowl XXVII 1993

Jackson’s stunning set, along with some trademark crotch-grabbing, sparked a cascade of top-name halftime stars and real extravaganzas. Future headliner Katy Perry watched Jackson’s halftime set for inspiration.

Diana Ross, Super Bowl XXX, 1996

This superstar knows how to make an entrance…and also an exit. She departed her Super Bowl set in a helicopter that landed exclusively to pick her up.

“Blues Brothers Bash”, Super Bowl XXXI 1997

Louisiana hosted the Big Game when the Green Bay Packers beat the New England Patriots 35-31 in ’97.

Sadly, though, behind the scenes, tragedy shadowed the show. Stuntwoman Laura Patterson died in a bungee jumping accident during rehearsal.

Jim Belushi subbed for his deceased brother John in the act, performing with Dan Ackroyd and John Goodman.

Prince, Super Bowl VLI 2007

On hearing from the producer that real rain would fall from the sky on his “Purple Rain” finale, perfectionist showman Prince asked, “Can you make it rain harder?”

M.I.A., Super Bowl XLVI  2012

Madonna would likely have been the most standout memory from the 2012 halftime lineup. But amid some energetic dancing, rap star M.I.A. flipped the bird. The screen blanked for a second, although that could have been the sponsors fainting.

The Federal Communications Commission (FCC) didn’t levy any fines but the NFL sued the performer for $16.6 million, settling in the end for an unknown amount.

According to, M.I.A. tweeted to Madonna, “@madonna ummm …. can I borrow 16 million?” 

Katy Perry, Super Bowl XLIX 2015

A shark sighting occurred at Super Bowl XLIX in 2015, rendering it one of the most memorable.

The halftime show featured top pop musician Katy Perry. She performed amid brightly colored beach balls and surfboards in between two performers in 7-foot blue shark costumes. The shark on the right stuck to the set choreography, but Left Shark— as he became popularly known — went rogue, or as he put it, he freestyled.

Sometime after the show, Perry tried to trademark “Left Shark.” It proved unsuccessful, but her sales increased 92% the week after the Big Game. 

Janet Jackson & Justin Timberlake, Super Bowl XXXVIII 2004 

We saved the undressed for last. AKA “Nipplegate.”

Even people who never watched a Super Bowl likely heard about this one. It is pretty much the most infamous halftime show ever. It launched the phrase wardrobe malfunction into the lexicon.

Towards the end of the halftime show, Justin and Janet did a duet and a pumping pas-de-deux to “Rock Your Body.” A sudden guest appearance took everyone by surprise: Timberlake seemingly tore Jackson’s top, exposing her bejeweled breast.

The FCC slapped 20 CBS-owned TV stations with a maximum indecency penalty each for a total of $550,000 in fines, at the time the largest FCC television fine ever.

FCC then-Chairman Michael Powell called the incident “more fitting of a burlesque show.” After leaving the chairmanship, however, he alluded to not being that upset.

More than half a million complaints about the cameo appearance were logged by the FCC. According to ratings, though, that left well over 100 million viewers who didn’t complain.

Even Timberlake admitted the unfairness of Jackson taking more heat for the incident than he did. And to this day, articles and discussions about the event still show up online.

Photo by Jai Agnish / shutterstock
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Marian Rosin

Marian Rosin is a freelance writer that has written on a variety of topics including publications like Upnest and Psychology Today. Marian brings experience in the gambling sector as the senior copywriter for Isle of Capri casinos.

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