Most Memorable Super Bowl Halftimes, 1990s-2000s

Written By Marian Rosin on December 28, 2021 - Last Updated on March 4, 2022
Highlighting the most remembered Super Bowl halftime shows

Before 1970, Super Bowl halftime shows consisted mostly of marching bands. Although, the Three Stooges performed in the first Super Bowl halftime show in 1967.

After 1970, marching bands thinned out and popular entertainment stole the show. Some shows have been controversial and some funny, intentional or otherwise. Some ranked as just plain great. And the exposure doesn’t hurt the performers, either. 

This article highlights some of the most memorable halftime shows in Super Bowl history.

#1 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 when her turn came.

#2 Rockin’ Country Sunday, Super Bowl XXVIII 1994

Georgia, represent! The Georgia Dome hosted country stars Clint Black, Tanya Tucker, and Wynonna and Naomi Judd. For the first time, the main stadium lights were turned off for the half-time show.

#3 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.

#4 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?”

#5 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?” 

#6 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 dancing beach balls and surfboards and 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. 

#7 Janet Jackson and 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 were doing 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 railway fx / shutterstock
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