Most Memorable Super Bowl Halftime Shows: 1990s – 2010s

Written By Marian Rosin on January 12, 2022 - Last Updated on February 2, 2022
Super Bowl halftime shows have featured some memorable performances over the years

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 mid-field surprise.

After 1970, marching bands thinned out, and more elaborate popular entertainment productions became the norm, sometimes literally stealing the show.

Some Super Bowl halftime shows have been controversial, and others were funny, intentionally or otherwise. Regardless, the exposure doesn’t hurt the performers, either—most of the time.

Let’s look back and highlight some of the most memorable shows in recent Super Bowl history.

Michael Jack grabs ratings – Super Bowl XXVIII, 1993

Michael Jackson’s stunning set brought trademark crotch-grabbing and sparked a cascade of halftime star extravaganzas. His blockbuster performance remains one of the most-watched events in American television history. Katy Perry used Jackson’s set for inspiration when turning in her record-breaking performance 12 years later.

Diana Ross introduces diva energy – Super Bowl XXX, 1996

Miss Ross showed future halftime stars how to make an entrance and nail an exit. After demanding and receiving an extra ninety seconds beyond the standard set length, Miss Ross was lowered onto the field by crane. She departed her performance waving from the open door of a helicopter that landed exclusively to pick her up.

Prince reigns – Super Bowl VLI, 2007

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

After the performance, his assistant commented that he’d made history. His Royal Badness immodestly replied in Prince-ly fashion, “I always make history.”

M.I.A. flips – Super Bowl XLVI, 2012

Usually, Madonna would have been the most standout memory from the 2012 halftime lineup. But during some particularly energetic dancing, rap star M.I.A. decided it was a good time to flip the bird.

While the Federal Communications Commission (FCC) didn’t levy any fines, the NFL sued the performer for $16.6 million. In the end, the parties settled for an unknown amount.

But first, according to, she tweeted to Madonna, “@madonna ummm …can I borrow 16 million?” 

Katy Perry’s show-stealing shark – Super Bowl XLIX, 2015

A shark sighting helped put the Super Bowl XLIX halftime show in the record books.

Pop musician Katy Perry sang and danced amid brightly colored dancing beach balls and surfboards, in between two performers in 7-foot shark costumes. The shark on the right stuck to the choreography, but Left Shark— as he became popularly known — went rogue, or as he put it, “freestyled.”

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

Kansas City Represents! Super Bowls 1967, 1970 and 2020

Admittedly, it’s true: Missouri has never hosted the Super Bowl. 

But the Kansas City Chiefs do have a Super Bowl history of two wins, one loss, including one Super Bowl with a disastrous halftime show.

The First Super Bowl

The Chiefs played in the first Super Bowl ever. Originally called the AFL-NFL World Championship in 1967, the game was later rechristened “Super Bowl 1.” In addition to the marching bands, chorus, balloons, and pigeons, a pair of jet-pack flying men representing the competing leagues capped off the show by landing for a 50-yard line handshake.

The halftime show fiasco of 1970

The Chiefs’ appearance in Super Bowl IV pitted them against the Minnesota Vikings in New Orleans. The entire event began as a textbook illustration of Murphy’s Law in action.

An hour before the game came a tornado warning. Next, a hot air balloon crashed into the stands, fortunately injuring no one. A microphone malfunction disrupted a dramatic reading of the pre-game national anthem. 

Murphy’s Law continued into the halftime show. A hot air balloon race fizzled when the second balloon couldn’t lift off. A model steamboat couldn’t sail. A horse was startled by a cannon during a reenactment of the Battle of 1812 and botled. In the midst of this mayhem, the first halftime show celebrity singer, Broadway’s Carol Channing, attempted to belt out her number.

And yet, despite the many bad omens, the Chiefs won.

And, of course, they won again in 2020. Happily, halftime LIV, starring Jennifer Lopez and Shakira, lacked the misfortunes of halftime IV.

Could the Chiefs see another show this year?

As of January 5, Las Vegas oddsmakers think recent history might repeat itself. They favor the Chiefs to make the Super Bowl from the AFC, despite the team’s number 2 seeded position on that date.

If they pull off the win, the Super Bowl LVI halftime show could be the Chief’s fourth.

While sports betting legislation is on the agenda for Missouri lawmakers this session, expect no decision before this year’s big game. Meanwhile, Show-Me State gamblers can find sports betting action across state lines in three directions like they did last year.

Janet Jackson and Justin Timberlake – Super Bowl XXXVIII, 2004 

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

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.

The halftime show was building to the finale. Justin and Janet did a duet and a pumping pas-de-deux to “Rock Your Body.” A sudden guest appearance surprised everyone: Timberlake seemingly tore Jackson’s top, exposing her bejeweled breast.

The FCC logged over 500,000 complaints about the “malfunction.” Although, by the ratings, over 100 million viewers didn’t complain.

Twenty CBS-owned TV stations faced a total of $550,000 in fines each. It was the largest FCC television fine levied to date.

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

Timberlake admits the unfairness of Jackson taking more heat for the incident than he did. And to this day, articles and discussions about the event show up online, making it the most memorable Super Bowl halftime show…so far.

Photo by Tyler Kaufman/Associated Press
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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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