Most Iconic Super Bowl Halftime Shows

Iconic Super Bowl halftime shows

Football sure has changed a lot in the last 50 years. Watching one of the early Super Bowls is like stepping into a time machine, and travelling back to when the NFL was played by smaller men in larger shoulder pads. The offensive linemen of the late 1960s were the size of today’s quarterbacks, and the entertainment wasn’t seen as important as it is today. With this in mind, it’s worth noting that a lot of the most iconic Super Bowl halftime shows will be from recent history.


The Super Bowl Halftime Show has evolved, too. It isn’t about marching bands anymore; when Rihanna takes the stage at State Farm Arena in Glendale this February 12, it will be one of the biggest moments of Super Bowl LVII – and the halftime show betting will be as intense as the Super Bowl betting itself.

To get you in the spirit, here’s our five most iconic Super Bowl halftime shows, listed in chronological order and spanning the entire era of pro football’s biggest spectacle. These aren’t necessarily the best or the most popular Super Bowl halftime shows – our apologies to fans of Beyonce and Lady Gaga – but they are the ones that gave us the most memorable moments and set the culture for years to come.

1. Super Bowl V: Up With People

We have to start with the college-style Marching Band Era, and the first appearance of Up With People, the song-and-dance troupe that promotes socially positive themes like peace and harmony. This halftime show at Miami’s Orange Bowl featured the Southeast Missouri State Marching Band with a special appearance by Anita Bryant singing “Battle Hymn of the Republic,” but it was Up With People who stole the show; they would be the headline act for their next four halftime appearances.

Technically, Up With People reached their zenith with their Salute to the 1960s and Motown show at Super Bowl XVI, which was held at the Pontiac Silverdome in Detroit. That show was a critical disaster – in part because they did away with the marching bands – and looks even worse today given that most of the cast were European-American. But we went with Super Bowl V because it represents everything the Super Bowl halftime Show used to be, even if Carol Channing wasn’t involved that year.

2. Super Bowl XXVII: Michael Jackson

Football historians say the Marching Band Era ended when New Kids on the Block crashed the party in 1991, but it was Michael Jackson who put the final nail in the coffin two years later at the Rose Bowl in Pasadena, California. This was the first halftime show that saw viewership increase instead of go down, with Jackson singing “Billie Jean” and “Black or White” and doing his signature moonwalk in what music critics call his last great live performance.


Jackson’s career (and his off-stage life) went off the rails from here, but this is the halftime show that set the precedent for what was to come – for better and for worse, as we shall see momentarily.

3. Super Bowl XXXVIII: Janet & Justin

This turned out to be the most iconic halftime show of them all, but not necessarily on purpose. Most people have forgotten that Jessica Simpson, P. Diddy, Nelly and Kid Rock were part of the show at Reliant Stadium; however, anyone who was old enough remembers Michael Jackson’s sister Janet and the infamous wardrobe malfunction at the end of her duet with Justin Timberlake.

If you didn’t happen to catch it, Jackson and Timberlake capped off this MTV-produced show by performing “Rock Your Body” from Timberlake’s first solo album. Timberlake sang the last line: “Gonna have you naked by the end of this song.” Then he reached across and tore away part of Jackson’s costume, revealing her right breast covered by a nipple shield and nothing else. Talk about one of the biggest Super Bowl shocks!

Everyone associated with the show said this was unintentional, and that Jackson was supposed to have a red lace brassiere over top of what we saw – thus the “malfunction.” Whatever the case, this moment did great damage to Jackson’s career, and the next batch of halftime shows would mostly feature classic rock and roll acts like Paul McCartney and the Rolling Stones. For better or worse, this had to be included in our most iconic Super Bowl halftime shows.

4. Super Bowl XLI: Prince

It’s impossible to categorize Prince. His halftime performance at Dolphin Stadium stands out among the shows from this era; Prince put his smash ‘80s dance hit “1999” in his set list, but it was mostly rock, including covers of “Proud Mary” and “All Along the Watchtower.”

Most importantly, Prince wrapped up his show with the ballad “Purple Rain,” and it just happened to be raining in Miami Gardens at the time. The sight of Prince playing his guitar – the one shaped like the symbol he used as his name when he was The Artist Formerly Known as Prince – and absolutely shredding that extended solo while the rain was coming down will not soon be forgotten.

5. Super Bowl XLIX: Katy Perry

Left Shark. Those two words perfectly encapsulate the current era of pop-oriented Super Bowl Halftime Shows, which began in 2011 with The Black Eyed Peas and will continue next month when Rihanna takes the stage in Glendale.

The same venue (then known as the University of Phoenix Stadium) played host for Perry’s show at Super Bowl XLIX, and again, not too many people remember that Lenny Kravitz and Missy Elliott were there. Perry and her hyper-colourful dance team were the centre of attention, especially when she sang “Teenage Dream” while flanked by two dancers in shark costumes.

The shark to Perry’s right – or stage left – was back-up dancer Bryan Gaw, and his dance moves were, shall we say, eclectic. This was done on purpose, and was meant to be a fun take on Perry’s own dance styles. It didn’t translate quite the way they expected; Left Shark became an instant meme, as did Right Shark, Drunk Shark and Basking Shark. Can Rihanna top that? We’ll soon find out.

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