Kendall Jenner awkwardly watches ex Bad Bunny carry out from her luxurious field at Super Bowl 2026

Justin Timberlake exposing Janet Jackson’s breast (2004)

The biggest fracas in Super Bowl halftime history was Janet Jackson’s infamous ‘wardrobe malfunction’ during her performance alongside Justin Timberlake.

Jackson was initially hired for the gig two years beforehand, only to be replaced with U2, who were thought to be a more suitable choice for the emotional post-9/11 performance.

However once Jackson finally managed to get on the halftime stage, her career imploded.

While whirling through their choreography, Timberlake notoriously tore off a piece of Jackson’s top, causing one of her breasts to be momentarily exposed to millions of viewers.

Over half a million complaints flooded into the Federal Communications Commission, with 65,000 of them coming from the Parents Television Council alone.

Jackson was blackballed from the industry, with radio and TV banning her songs and music videos. A planned biopic of Lena Horne, which she was to star in, also fell through as a result of the scandal.

Timberlake refrained from publicly defending Jackson and did not even apologize for causing her wardrobe malfunction until 2021, when a documentary about his ex Britney Spears led to his getting deluged with public opprobrium over his treatment of women.

Kendrick Lamar’s ‘say Drake’ (2025)

Kendrick Lamar divided Super Bowl fans last year after bringing his 13-year feud with Drake to a global stage, performing his viral diss track in a set dubbed the ‘worst halftime show ever’.

The massive platform offered him a chance to take a swipe at his rap rival – teasing Not Like Us throughout his set before performing a redacted version of the controversial track. 

In addition to performing the song – which he was sued for because it includes lyrics labelling Drake a ‘certified pedophile’ – Kendrick brought out Serena Williams, who is also in a feud with the Canadian rapper. 

Kendrick opted not to say pedophile so as not to trigger another lawsuit, telling the crowd, ‘I want to perform their favorite song, but you know they love to sue.’ 

He did, however, go on to deliver two other controversial lines, including ‘Say Drake, I hear you like them young’ and ‘trying to strike a chord and it’s probably a minor,’ as the crowd sang along. 

The moment became a massive meme which circulates around internet to this day.       

He also wore a big silver chain pendant with a small letter ‘a’, in another reference to ‘A minor’ in the lyrics. 

Rihanna’s pregnancy reveal (2023)

Multiple time Grammy Award winner Rihanna confirmed she was pregnant with her second child after surprising fans with a baby bump during her highly anticipated comeback at the Super Bowl in 2023.

The A-lister, who gave birth to her first child just nine months previously, sent social media into a frenzy as she took to the stage and rubbed her tummy in front of a global audience of millions at State Farm Stadium in Glendale, Arizona, where the Philadelphia Eagles are taking on the Kansas City Chiefs.

A representative for star confirmed the baby news shortly after the performance finished.

It marks the first time she has performed on live television since 2018, where she joined DJ Khaled on stage to sing Wild Thoughts at the Grammy Awards. 

Rihanna started off the show suspended on a platform high above the field as she belted out her single B**** Better Have My Money. She was dressed in a baggy scarlet jumpsuit that covered up her curves and was strapped loosely on her. 

However, she wore a skin-tight bodysuit underneath that highlighted her burgeoning baby bump. 

She shares her first child, who was born on May 13, 2022, with the rapper A$AP Rocky, who kept a low profile at the event.

Daughter Riot Rose was born on August 1, 2023. They have since welcomed a third child: daughter Rocki Irish born in September 2025.

Katy Perry and left shark (2015)

The infamous Left Shark first appeared when Katy Perry performed at the Super Bowl XLIX Half Time Show in 2015.  

The shark – played by Katy’s tour dancer Bryan Gaw – rose to fame after appearing to dance out of sink with the music and with his fellow costumed dancer to the right of Katy as she sang her hit California Gurls.

The oddly timed free-style dancing immediately went viral, quickly becoming the highlight of Katy’s musical performance.

Speaking to NPR, Bryan said that the off-kilter dance moves were rehearsed as he wanted to play a ‘character’ in the large shark costume.

Chatting to the station, he said: ‘There’s what’s called free-style choreography, or, like, you get to move around or play your character as a dancer.

‘I’m in a 7-foot blue shark costume. There’s no cool in that. So what’s the other option? Well, I’m gonna play a different character.’ 

Eminem takes a knee (2022)

Eminem famously took a knee during a 2022 performance despite official NFL rules effectively banning players from performing the gesture made famous by Colin Kaepernick during the anthem.

The rules state ‘all league and team personnel shall stand and show respect for the flag and the anthem’ with players that refuse to stand asked to ‘stay in the locker room until after the anthem has been performed.’ 

Eminem made the gesture, which has become a symbol of protest against racism, after he finished his performance of his hit song Lose Yourself.

In what would appear to be his moment to bow, Eminem – real name Marshall Mathers – dropped to the ground on one knee, with his head hanging solemnly.

He maintained the position for approximately 50 seconds as the performers transitioned into Snoop Dogg’s set.

Eminem did so even though no players from the Rams or Bengals knelt during the National Anthem at the start of the game – and there was no sign of any other kneeling from the audience either.

Michael Jackson stands in silence for two minutes (1993) 

 The Super Bowl halftime show has become just as anticipated as the game itself and many credit Michael Jackson‘s 1993 performance as the one that completely changed the game.

The King Of Pop was in the prime of his career at 34 years old when he took the stage at the Rose Bowl in Pasadena California at Super Bowl XXVII on January 31, 1993, which would become one of the most-watched events in American television history with a near unbelievable 133.4million viewers.

The 12-and-a-half minute show was groundbreaking as it featured many elements including body doubles, a catapult entrance, and nearly two minutes of silence.

Michael’s performance is considered as one of the most iconic in the event’s history and he is credited as elevating the gig to a completely new level. 

Michael’s performance began with a James Earl Jones voiceover as he called it an ‘unprecedented Super Bowl spectacular starring Michael Jackson’.

The Bad hitmaker then seemed to appear at the top of the stadium’s two jumbotrons only to find out they were actually body doubles.

Then Michael was finally revealed as he was catapulted from center stage and then stood completely frozen and silent for nearly two minutes as the crowd raucously cheered on in arguably the most iconic moment of the performance. 

Prince performs Purple Rain in the pouring rain (2007) 

Dressed in his signature color purple, Prince performed on a stage shaped like his ‘love symbol’ – the same one he had temporarily changed his name to in the 1990s.

Although the halftime show traditionally takes place in the open air at the center of the stadium, Prince’s gig marked the first time it rained.

Prince shrugged off the dangers of using equipment like electric guitars under a downpour, and in fact adored the challenge, to the point he reportedly wished it would ‘rain harder’.

He treated the crowd to a medley of not just his own numbers but those of other musical icons, including Creedence Clearwater Revival’s Proud Mary and Bob Dylan’s All Along The Watchtower.

His closer was, aptly enough, Purple Rain, culminating in a fireworks display.

M.I.A. flips the bird (2012) 

British singer and rapper M.I.A. was a special guest during Madonna’s performance in 2012.  

However, censors did not expect the musician – born Maya Arulpragasam – to stick her middle finger up during the performance as they were unable to blur it in time from the live broadcast.

M.I.A. and Nicki Minaj had joined Madonna on stage for a performance of the single Give Me All Your Lovin’.

Both the NFL and NBC – who was broadcasting the massive event at the time – issued apologies and there was no action taken by the FCC. 

NBC spokesman Christopher McCloskey said in a statement: ‘We apologize for the inappropriate gesture that aired during halftime. 

‘It was a spontaneous gesture that our delay system caught late.’

NFL spokesman Brian McCarthy added: ‘The obscene gesture in the performance was completely inappropriate, very disappointing, and we apologize to our fans.’ 

50 Cent comically hangs upside down (2022) 

Rapper 50 Cent made a surprise appearance and his drop-in went viral at the time.

The musical artist emerged on stage swinging upside down from the rafters – hanging like a bat – and rapped for the crowd of 70,000 people at SoFi Stadium in Inglewood, California.

The rap artist, whose real name is Curtis James Jackson III, was a part of the ensemble performance with Dr. Dre, Snoop Dogg, Mary J Blige, Eminem and Kendrick Lamar, performing his 2003 hit In Da Club.

The upside down opening was a takeoff on the video the rapper released for the track, as he was seen pictured in a medical lab upside down.

A number of social media users poked fun at the unexpected presentation of the singer, with some likening his emergence to superheroes such as Spider-Man and Batman, or Star Wars protagonist Luke Skywalker in The Empire Strikes Back.