5 worst Super Bowl halftime shows ever

By Vincent Frank

·Updated: February 12, 2023

What are the five worst Super Bowl halftime shows ever? Are the legendary Rolling Stones included? Heading into Rihanna’s performance at halftime of Super Bowl LVII, we’ve already checked in on the five-best Super Bowl halftime shows. That list includes last year’s iteration with Dr. Dre and several other hip-hop icons. Other genres including U2 and the late-great Prince are also included.

In looking at the five-worst Super Bowl halftime shows ever, you’re going to see some legends outside of the aforementioned Rolling Stones. Without further ado, let’s check them out.

5. Winter Magic: Super Bowl XXVI

As Washington and Buffalo took to the field for the big game back in January of 1992 inside the old Metrodome in Minneapolis, the NFL thought it made sense to pay homage to Christmas. The problem was that this game took place a month after Christmas itself. It also included a show that could have been seen for $5.00 at some random off-strip casino in Las Vegas.

We’re not even sure where to start with this one. From the d-list celebrities to the disastrous dancing, horrible music and graphics that seemed like they came from the 1950s, this was terribad. Just over-the-top generic stuff that made choreographers everywhere vomit in their mouths.

4. Blues Brothers: Super Bowl XXXI

Oscar Mayer never promoted a Super Bowl halftime show after this disasterclass back in January of 1997. From the inclusion of Fox News (that was a thing) during the show to the tragic death of a bungee-jumper in practicing for the event, this thing was doomed to fail from the start.

Dan Aykroyd, John Goodman and Jim Belushi were pegged to perform with ZZ Top and James Brown (weird fitting) to promote their upcoming movie Blues Brothers 2000. Much like one of the worst Super Bowl halftime shows ever, that bombed.

3. Rolling Stones: Super Bowl XL

We’re not agists over here at Sportsnaut. But something did not feel right about a 62-year-old Mick Jagger trotting around and shaking his hips on stage inside Ford Field as the Pittsburgh Steelers and Seattle Seahawks did battle.

The most cringe-worthy moment of this performance was when teenagers who weren’t even born when the Stones were in their heyday crushing on Jagger and Co. We will give the Stones credit for performing only three songs. They also rocked with Satisfaction. Even then, this one seemed forced.

2. New Kids on the Block: Super Bowl XXV

Hours before this boy band took to the stage to perform under the theme of it’s a small world, Whitney Houston dazzled the crowd inside Tampa Stadium with her rendition of The Star-Spangled Banner. The backdrop was America’s recent invasion of Iraq and the start of the Desert Storm War. Patriotism was at an all-time high.

Well, Donnie Wahlberg and Co. failed the read the room. The performance itself was all over the place and was seemingly put together on a whim. In fact, a special report on the war in the Middle East forced this to be aired after the game. For good reason. It was an absolute disaster. For good measure, Wahlberg was seen wearing a “War Sucks” t-shirt at the American Music Awards a couple weeks later. Barf-worthy stuff here. Yes, this was one of the worst Super Bowl halftime shows ever.

1. Janet Jackson and Justin Timberlake: Super Bowl XXXVIII

These two legends actually performed well on the stage. But it was all about Janet’s nipple coming into view for the hundreds of millions tuning in for the Tampa Bay Buccaneers and then-Oakland Raiders game in San Diego. The world seemed to stop. How could Janet let that happen? A nipple. Oh, the humanity.

Sarcasm aside, Timberlake’s response to the incident was cringe-worthy with the former boy band star trying to take the moral high-ground. Janet was pretty much canceled before cancel culture became a thing. More than anything, the changing of pop culture that came with this innocent mishap makes this one of the worst Super Bowl halftime shows ever. It’s a crying shame because the two actually put on a heck of a show.