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The Most Awkward Super Bowl Halftime Shows

There are three reasons people watch the Super Bowl: sports rivalry, ridiculous commercials, and the possibility that something completely unexpected will happen during the halftime show. Here are 10 halftime performances that were memorable for all the wrong reasons! From uninspiring, lackluster performances to the wardrobe malfunction seen 'round the world, these Super Bowl halftime performances were just not up to snuff. 

Super Bowl LVII (2023)

Super Bowl LVII (2023)

Many people were impressed with Rihanna’s extravagant and artful display at the 2023 Super Bowl halftime show, but not everyone. Numerous viewers noticed that Rihanna was lip-synching throughout her performance, making the whole thing less impressive. And it wasn’t necessarily just that she was lip-synching.

It’s that she was doing it very poorly. Sure, undoubtedly, there have been numerous lip-syncing performances at the Super Bowl over the years, but not all of them have in-your-face lip-syncing front and center. Maybe we could cut her some slack, given that she’s pregnant, but its still doesn’t take away from the awkwardness of it all.

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Super Bowl XXIX (1995)

Super Bowl XXIX (1995)

In a shameless promotion of the new Disneyland Indiana Jones-themed ride, Disney came up with a Indiana Jones-inspired show full of stunts and spectacle. The show featured full sets and even characters from the franchise. The obvious marketing was mega-cringe and hard to watch.

Guest singers at the halftime show were Patti LaBelle and Tony Bennett, but the ridiculous show easily overshadowed them. For being part of a show between a football game, you would think these shows would try harder to cater to actual footballs fans, but no – it’s all about marketing.

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Super Bowl LIII (2019)

Super Bowl LIII (2019)

Another band nobody really cares about anymore – Maroon 5. After Colin Kaepernick controversially took a knee back in 2016 as the national anthem played, no NFL team would sign him. In response to his cancellation by the NFL, many music artists elected not to participate in the 2019 halftime show – except Maroon 5.

Having no other important gigs, Maroon 5 answered the call and nobody would have cared, literally, if it were not for the controversy surrounding the event. Maroon 5 was subjected to much backlash for participating in the event. And in an attempt to rescue their PR, they donated 500,000 dollars to Big the Brothers and Big Sisters of America program.

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Super Bowl LII (2018)

Super Bowl LII (2018)

In 2018, Justin Timberlake performed in Minneapolis. Everyone was expecting a tribute to legendary music artist Prince, but was hoping that the performance would not disrespect Prince’s memory by  utilizing a hologram, technology that Prince was adamantly against.

However, that ended up being exactly what Justin Timberlake did. Justin Timberlake sang alongside a digital projection of Prince from the film Purple Rain. After singing “I Would Die 4 U” at the halftime show, he received much backlash from Prince fans, in particular, the diehard fans. Definitely awkward.

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Super Bowl XXX (1996)

Super Bowl XXX (1996)

Diana Ross was a bit extra in 1996 when she exited her halftime show in a helicopter. The helicopter landed in the field mid-performance and at the end was whisked away. It was totally awkward but also kind of cool. But when we look back at it know, it was mostly just dumb.

Could she have just walked off the field like a normal person? Absolutely, but Diana Ross is a larger than life music legend so she had to go all out. Was the helicopter really the way to do it though? There really wasn’t a lot of thought put into it. It amazed people cause it was a helicopter and how many people have those at home?

Al Bello/Staff/Getty Images Sport/Getty Images

Super Bowl XLVI (2012)

Super Bowl XLVI (2012)

Madonna just seems to constantly embarrass herself in a variety of ways, and the 2012 Super Bowl halftime show was no exception. She tried her very hardest on stage and that’s exactly what it looked like too. It was completely evident she was not aware she is well out of her prime.

As she danced and lip-synched her little heart out, all the audience could see what a subpar performance from a middle-aged popstar, still trying to retain their relevance. It wasn’t a terrible half-time show overall, but with Madonna’s part, it was incredibly awkward.

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Super Bowl XXXII (1998)

Super Bowl XXXII (1998)

To celebrate their Motown inspirations, Boyz II Men were joined by Smokey Robinson, Martha Reeves, and The Temptations. Following the aging performers, Boyz II Men had absolutely no stage presence and just put everyone to sleep. And considering the fact that the halftime show is always such a flashy spectacle, there's just no excuse for a lackluster performance.

Were they nervous? Was it better during dress rehearsal? The world may never know. What we do know is that this was a performance we'd rather forget. Credit where credit is due, though—the best part of the set was the Grambling State University marching band.

 

(Image via YouTube)

Super Bowl XLIII (2009)

Super Bowl XLIII (2009)

For the most part, Bruce Springsteen’s performance was amazing. He played hits spanning his long career and he wasn’t forced to collaborate with anyone outside of his musical range. However, he did manage to slide crotch-first into a camera. Like a professional, that didn’t stop him from finishing the set.

Seeing the Boss's bulge, didn't quite ruin the show for everyone but it was an awkward moment for just about every, especially if you were watching with the whole family.  It was also an incredibly awkward moment by the fact that Springsteen is much too old to be acting like that.

(Image via YouTube)

Super Bowl XXV (1991)

Super Bowl XXV (1991)

In an attempt to get adolescent viewers to tune in, ABC decided to get boy band New Kids On the Block to perform with enormous versions of beloved Disney characters. Years later, Donnie Wahlberg posted a video of the show, saying, “I’d rather eat rusted nails than watch this but, in the spirit of the game, maybe you’ll enjoy.”

The Disney characters were undoubtedly a gimmicky marketing attempt that was more awkward, and no pun intended, goofy. For the future, hopefully, Disney has learned there's a time and place to pitch its products and the Super Bowl halftime show is not that time nor place. 

(Image via YouTube)

Super Bowl XXVII (1993)

Super Bowl XXVII (1993)

Always the showman, Michael Jackson had two body doubles pop up on either side of the stadium before the actual King of Pop burst onto the stage from underneath. Afterward, he stood still for a full minute and 30 seconds without moving. Maybe this was cool by 1993 standards, but it felt very forced and left Jackson with almost no time to perform his hits. 

 

Oh, and he decided to sing “We Are the World.” Really, Mike? Super Bowl isn't a time to be corny; it's a time to be cool. Michael Jackson's extraness was not really a place for the Super Bowl, and that should be apparent. Enough time has passed since his death that its okay to say this now.

(Image via YouTube)

Super Bowl XLIX (2015)

Super Bowl XLIX (2015)

During Katy Perry’s halftime performance, she was joined onstage by Missy Elliott, Lenny Kravitz, and two dancers in shark costumes. The shark on the left of Perry apparently missed his mark and was completely out of step with the rest of the performers. The Left Shark became the most talked about aspect of the game due to its hilarious awkwardness.

 

Honestly, though, the halftime show probably wouldn't have been nearly as memorable without it. Katy Perry is slowly but surely fading in terms of relevance but this halftime show we'll never forget, even if it's just because of the shark.

(Image via YouTube)

Super Bowl XXXV (2001)

Super Bowl XXXV (2001)

The inclusion of Aerosmith, 'NSync, Britney Spears, Mary J. Blige, and Nelly was most likely an attempt to reach as many types of fans as possible, but it just came off as an awkward jumble of performers. Hearing each artist butcher another's song is enough to make you never want to listen to any of them ever again.

 

When Super Bowl halftime shows try this hard to appeal to the masses, the results are never good. Just pick one thing and if people aren't pleased, well, try again next year. You can't please everyone and in attempting it, you end up with an inferior product. 

(Image via Youtube)

Super Bowl XXXI (1997)

Super Bowl XXXI (1997)

As if it wasn’t bad enough for Dan Aykroyd and John Goodman to ruin The Blues Brothers with a terrible sequel, they took the stage at Super Bowl XXXI to promote the film. James Belushi stood in for his late brother John, which was just another reason why this never should have happened.

You can't replace a legend with your less famous brother - but they tried. James Brown joined them for a couple of songs, but he was upstaged by three awkward actors. We've forgotten amlost everything about the second Blues Brothers movie and we wish we could forget about this halftime show too.

 

(image via Youtube)

Super Bowl XXIII (1989)

Super Bowl XXIII (1989)

Back in 1989, the Super Bowl halftime show wasn’t always the big spectacle it is today. The star of the performance was Elvis Presto, an Elvis impersonator and magician. When he took the stage, he had the audience participate in a singing card trick as dancers showed off the height of 1980s fashion against an interstellar backdrop.

 

But this was undoubtedly one of the strangest halftime shows that ever was. The Elis impersonator didn't not perform even one song from The King. And we haven't even mentioned the goofiest part of the whole thing - that being the 3D sequences in the show that audiences enjoyed with 3D glasses, courtesy of Coca-Cola. 

(Image via Youtube)

Super Bowl XLV (2011)

Super Bowl XLV (2011)

It’s hard to remember that the Black Eyed Peas were once one of the biggest musical acts in the world. Their Super Bowl performance didn’t make a great case for them. The worst moment was when Slash came out and began playing “Sweet Child o‘ Mine" as Fergie tried to do an Axl Rose impression.

 

It was an awkward moment for a lot of reasons, but looking back on it, its even worse than we imagined. Now that the veil has been taken off and the Black Eyed Peas are essentially a punchline, we can look back on this halftime show with nothing other than regret. 

(Image via YouTube)

Super Bowl XLV (2011)

Super Bowl XLV (2011)

The time of the Black-Eyed Peas has come and gone. Everyone has had just about enough of the Black-Eyed Peas, so I think we are safe in addressing the fact that their 2011 Super Bowl performance was one of the most awkward events in Super Bowl history. It was just plain bad.

Partnering up with Slash from Guns & Roses, the Black-Eyed Peas ended up completely butchering “Sweet Child O’ Mine.” Fergie provided the vocals in what must be the worst rendition of the song to-date. She didn’t even try to do her own thing, she tried to make her voice sound like Axl Rose and it was super cringy.

Tom Hauck/Getty Images Sport/Getty Images

Super Bowl XLVIII (2014)

Super Bowl XLVIII (2014)

In 2014, the legendary alternative rock band, The Red Hot Chili Peppers was decidedly uncool when they faked their performance at half-time. But it wasn’t the vocals that were faked this time around. Rather than lip-synching, they instrument…synched…fake playing their instruments without any sound.

Many diligent viewers noticed that the Red Hot Chili Peppers were performing without their instruments connected to the amplifiers and yet the music went over the stadium speakers. All of the instrumentals had been pre-recorded, so the band basically air-guitared their way through it.

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Super Bowl LI (2017)

Super Bowl LI (2017)

Lady Gaga definitely has a taste for the dramatic, famously wearing a dress made up of meat to make a statement, so it should come as no surprise she’d do something bizarre like appear as though she’s jumping off the football stadium and onto center stage. Of course, that didn’t really happen

And you could tell it didn’t really happen because, who jumps like that? The whole thing was prerecorded and made to look like she was doing that for the benefit of television audiences but the whole display was exceedingly awkward and genuinely uncomfortable to watch.

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Super Bowl XXXVIII (2004)

Super Bowl XXXVIII (2004)

In the most talked about halftime show of all time, millions of viewers saw Janet Jackson’s exposed breast. Whether the wardobe malfunction was intentional is still widely debated, but it overshadowed every other aspect of the game. You probably don’t even remember that P. Diddy and Kid Rock were there, too!

This is honestly one of the most iconic Super Bowl halftime moments of all time, as well as one of the most awkward. For months, people were still talking about it and it feels like just yesterday. We doubt there's a nipple more famous than hers to be quite frank.

Super Bowl XXXVIII (2004)

Super Bowl XXXVIII (2004)

The whole fiasco was dubbed "Nipplegate," with many wondering if the entire moment has been staged for the sake of ratings. The show, had, after all, pulled in 140 million viewers. And Jackson, herself, had refused to talk about it, with her publicist refusing to comment altogether. 

There was a lot of commotion over that little brown protrusion, and it ended up changing television forever as there was an immediate crackdown by the FCC on perceived indecency in broadcast television. Ultimately, it was a great moment for the NFL as it generated an audience of people waiting to see the next nipple if you will.

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