Top 20 Cringiest Halftime Show Moments

Top 20 Cringiest Halftime Show Moments

Welcome to WatchMojo, and today we’re counting down our picks for the Top 20 Cringiest Halftime Show Moments.

For this list, we’ll be looking at the Super Bowl Halftime Shows that were either offensive or just plain awkward to sit through at the time. Even if the musical moments were good, there was always something about it that made you want to shut the TV off.

What halftime show made you wince the hardest? Let us know in the comments.

#20: The Left Shark

“Super Bowl XLIX” (2015)
Katy Perry’s performance at the Super Bowl XLIX halftime show is one of the most viewed in history… but not because of Katy herself. To set the scene, she performed “Teenage Dream” on a cartoony, tropical stage -which included two dancers dressed as sharks. Despite the bizarre setting, what really caught the audience’s attention was the left shark. It couldn’t quite keep up with the show’s choreography and looked very out of place on stage. Viewers couldn’t stop talking about the “rogue” shark and it became an instant meme. It was ridiculous at the time, though the organizing choreographer later claimed it was intentional. Regardless, fans nowadays look back at the poor shark with fondness, knowing that the dancer was doing their best.

#19: M.I.A. Gives the Finger

“Super Bowl XLVI” (2012)
Among the performers at Super Bowl XLVI’s halftime show, Madonna and M.I.A. were definitely the standouts. But while Madonna stood out for her performance and tribute, M.I.A. stood out for flipping off over 100 million viewers. The NFL didn’t censor her gesture in time and demanded a public apology from her. M.I.A., however, was having none of that – she fought back, citing athletes’ problematic behavior and arguing that the show’s provocative outfits were more inappropriate than her middle finger. Whether she’s right or not, her actions weren’t exactly professional, and they probably weren't worth the lawsuit. What should’ve been a fun spectacle for football fans turned into a debacle where no one was in the right.

#18: Spotty “Baba O’Riley” Vocals

“Super Bowl XLIV” (2010)
Just imagine it – it’s 2010, and The Who, arguably one of the greatest English rock bands ever, is performing at the Super Bowl halftime show. The big day arrives and you see them out in the field surrounded by some amazing pyrotechnics as they perform five of their biggest hits, and… it just doesn’t sound right. Unfortunately, many thought The Who were unable to bring their A-Game to the show – they sounded off-key and tired, instead relying on “audience sing-along” moments. A lot of fans can see past their less-than-stellar performance, but if you’re going to perform at the Super Bowl, you need to be prepared… and it unfortunately appeared like The Who wasn’t ready for this gig.

#17: Coldplay Overshadowed

“Super Bowl 50” (2016)
It’s been universally said that Beyonce SLAYED it at Super Bowl 50 with her new song, “Formation”. …Oh yeah, Coldplay was supposed to be there too, weren’t they? They were supposed to be the headliners while Beyonce and Bruno Mars were the special guests. While they did their best, they clearly didn’t have the energy to wow the crowd and seemed content to let Queen Bey and Mars carry the show for them. Even when they all sang together, Coldplay’s voices were practically drowned out by their guests, and whatever energy Martin had was wasted on jumps. If you’d rather let your guests carry your show than be the headliner people expect, then it might cause people to ask why you showed up at all.

#16: 50 Cent’s Supposed Lip Sync Fail

“Super Bowl LVI” (2022)
2022’s halftime show boasted a love letter to the hip-hop and rap genre, complete with a surprise appearance by 50 Cent among others. 50 Cent performed his original “In Da Club”, but when he gets down from the ceiling, there’s what many suspect to be a noticeable lip-sync from the rapper. Hanging upside down from the ceiling takes a lot of energy, and 50 Cent looked pretty out of breath after getting back down. Yet he “miraculously” didn’t skip a beat while conveniently having the microphone obscuring his lips. To his credit, the lip-synching gets less noticeable along the way, and it shouldn’t ruin what was a fun, heart-pumping tribute to the genre… but some little things are harder to ignore.

#15: Anything With ‘Up With People’

“Super Bowl V-XX” (1971-86)
It turns out that Disney isn’t the only company to be a recurring performer for the Super Bowl. Between 1971 and 1986, before the era of big-name performers, five halftime shows were orchestrated by the nonprofit organization, Up with People. Their shows were rather campy and upbeat, and are actually well-rehearsed and choreographed, with themes of education and culture. The problem – it wasn’t what football fans wanted. A few critics claimed their shows had a cultish, creepy vibe. They especially didn’t like the group’s performance for Super Bowl XVI, which featured the “whitest people in the world” doing a Motown tribute. However, fans breathed a sigh of relief when Up with People’s Super Bowl Halftime tenure finally ended.

#14: Gwen Stefani's Pushups & Weird Salutes

“Super Bowl XXXVII” (2003)
Super Bowl XXXVII’s halftime show brought a huge flux of girl power with Shania Twain and No Doubt at the forefront -with some extra support by Sting. Arguably, No Doubt overshadowed Twain…. But not in the way you’d think. For starters, Gwen Stefani’s audio sounded very off, but if that wasn’t enough – she started doing push-ups before beginning the act, and out of nowhere started saluting the audience. At the very least, she had plenty of energy to spare -which is good for performing at the Super Bowl, but she used most of it on these random feats that just felt out of place. We’ll say this, it was definitely a memorable show…. For better or worse.

#13: Peanuts Characters

“Super Bowl XXIV” (1990)
Poor Charlie Brown. Not only does he constantly fail to kick the football, but he also can’t even put on a good enough halftime show. For context, Super Bowl XXIV’s halftime show served as a tribute to both New Orleans and the 40th anniversary of the “Peanuts” comic strips. Part of this included having several performers dressed as characters from the strips, including Linus, Charlie Brown, Lucy, and Snoopy. Now, the show itself had a nice concept, but the Peanuts costumes just didn’t look right. They looked downright creepy with their mouths hanging open, and it’s clear the character designs didn’t translate well as mascot suits.

#12: The Blues Brothers

“Super Bowl XXXI” (1997)
In 1997, the Blues Brothers were on a mission from God – to perform at the Super Bowl and subsequently promote their new movie, “Blues Brothers 2000.” They aimed to do it with a “Blues Brothers Bash” concert alongside James Brown and ZZ Top… yes, a ROCK band in a BLUES tribute (alright, so they’re a blues rock band, but still). It goes without saying that the show was a trainwreck – a shameless promotional gimmick made even worse by them trying to replace the late John Belushi - one half of the original Blues Brothers. To be honest, we should count our blessings John never got to see this - not even James Brown could save it.

#11: A Disney-Filled Mess

“Super Bowl XXV” (1991)
In 1991, Disney produced the Super Bowl halftime show, and it’s hard to pinpoint which moment was the cringiest. It could have been the little kids dressing up like football players and cheerleaders while singing and dancing. Or it may have been costumed Disney characters including Minnie Mouse, Goofy, and Winnie-the-Pooh simply being part of the show. To top it all off, the main act for the halftime show was The New Kids on the Block, because that’s the perfect group to entertain and hype football fans, right? C’mon, Disney.

#10: Everybody Sings “Walk This Way”

“Super Bowl XXXV” (2001)
A lot of viewers are split about the "The Kings of Rock and Pop" show from Super Bowl XXXV. They can’t decide if it’s one of the best shows or pure insanity. Just picture this – Aerosmith and NSYNC teaming up to put on one big show before bringing Britney Spears, Mary J. Blige, and Nelly into the mix for one last explosive rendition of “Walk This Way”. While not really that bad and can be fun to look back on, it feels like this show was just trying too hard to be cool. You’d have to have been pretty young at the time to recognize the performers -plus seeing Britney and Justin together feels awkward given their breakup the following year.

#9: Christina & Enrique's Lifelessness

“Super Bowl XXXIV” (2000)
By this point on the list, we know that Disney’s track record with the Super Bowl hasn’t been great, but we give them credit for giving it the college try yet again. In 2000, to celebrate the new millennium, Disney orchestrated a concert for the Super Bowl with stars such as Phil Collins, Christina Aguilera, and Enrique Iglesias. While no one was necessarily bad, the show ended up falling flat due to it feeling way too slow and uninteresting. Worst of all, it felt creepy seeing Christina and Enrique so dull and lifeless given their usual more risqué performance styles. Overall, Disney wanted to celebrate the oncoming millennium, and instead just put viewers to sleep.

#8: A Halftime Show on Ice

“Super Bowl XXVI” (1992)
As part of the theme of “Winter Magic,” the 1992 halftime show featured performers dressed in white and blue dancing to “Winter Wonderland” and “The Nutcracker.” The show also highlighted the U.S. Olympic skating team, with notable skaters Brian Boitano and Dorothy Hamill getting a chance to show their talents on a stage that was converted to a skating rink. Unfortunately, the show was anything but magical. Once again, this is yet another case of a halftime show that focuses on trying to be original rather than appealing to the average football fan. Thankfully, the following year, the NFL got it right with Michael Jackson.

#7: Indiana Jones & the Shameless Marketing Gimmick

“Super Bowl XXIX” (1995)
For this halftime show, Disney decided to use an Indiana Jones theme to promote a new ride, Temple of the Forbidden Eye, which hit Disney theme parks that year. As expected, the show was a giant spectacle full of sets and characters from the film series. This included impersonators for Indiana Jones and Marion, who acted more like Willie from “Temple of Doom,” obnoxiously shouting “Indy!” when she was in trouble. Not even singers Patti LaBelle and Tony Bennett could save this train wreck.

#6: The Red Hot Chili Peppers Faking It

“Super Bowl XLVIII” (2014)
During the Red Hot Chili Peppers’ guest performance at Super Bowl 48, it was apparent to some viewers the band didn’t have their instruments hooked up, despite the loud sounds blaring from the speakers and enthusiastic guitar picking coming from the players. This led to accusations that the Red Hot Chili Peppers had faked their performance at the halftime show. Shortly after, the band came clean, and bassist Flea wrote a statement on the band’s website explaining their actions, saying that it was the NFL’s idea that “only the vocals be live” and “the bass, drums and guitar be pre-recorded.”

#5: Maroon 5

“Super Bowl LIII” (2019)
Following the controversy surrounding the unwillingness of NFL teams to sign quarterback Colin Kaepernick, several musical artists declined invitations to perform at the Super Bowl halftime show in 2019. However, Maroon 5 stepped up to the plate, and was criticized for doing so. Many believed that all major artists should have boycotted the halftime show to support Kaepernick and punish any company that silenced the protest. To defuse the controversy, the band decided to give 500,000 dollars to Big Brothers and Big Sisters of America, but the issue still hung over the band while they played their set.

#4: Fergie Singing ‘Sweet Child o’ Mine’

“Super Bowl XLV” (2011)
The whole Black Eyed Peas performance at this Super Bowl was a disaster, from their stilted dance moves to their outlandish outfits. When former Gun N’ Roses guitarist Slash first came out playing the opening riff to “Sweet Child o’ Mine,” it looked as though the show could be saved. But then Fergie started singing, killing any hope for momentum. Instead of performing the song with her actual singing voice, she opted to try and imitate Guns N’ Roses frontman Axl Rose, as if that’s something Slash or anybody else wanted to hear.

#3: An Elvis Impersonator’s Magic Flop

“Super Bowl XXIII” (1989)
Before the 1990s, Super Bowl halftime shows didn’t focus on pop stars. Case in point: the main act for Super Bowl XXIII’s halftime show in 1989 was an Elvis impersonator who performed magic tricks under the name “Elvis Presto.” We’re not joking. During the show, Elvis Presto, accompanied by backup singers, performed a card trick where the audience was asked to pick from four cards. The card they picked was based on how loud their applause was. Fortunately, the NFL decided not to continue in this direction for future halftime shows.

#2: A Tribute to Prince

“Super Bowl LII” (2018)
Playing in Minneapolis, Justin Timberlake decided to display a video projection of Prince on a large sheet as an homage to the late artist. Although Timberlake reportedly promised to not use a hologram of Prince during his performance, Timberlake sang “I Would Die 4 U” along with the video, part of which was taken from the movie “Purple Rain.” Although we wouldn’t necessarily classify this as a hologram, fans were outraged, feeling that the act was still being disrespectful to Prince’s memory. Interestingly enough, Prince himself previously went on record to express disapproval of technology that brought back musical legends for collaborations, so Timberlake most likely wouldn’t have had his blessing.

#1: Janet Jackson’s ‘Wardrobe Malfunction’

“Super Bowl XXXVIII” (2004)
Unsurprisingly, Justin Timberlake also takes the top spot for his appearance at the 2004 halftime show where he removed a piece of clothing from Janet Jackson, showing TV viewers one of her breasts. Whether this was the intended climax of the halftime show or an honest wardrobe malfunction, this incident brought the show to a screeching halt, with Jackson covering herself with a look of shame. Then, of course, there was the outrage from angry parents, and the clip was shown repeatedly on television so we could relive the cringe over and over and over again...