Top 20 UNBEARABLY Awkward Live Musical Performances
#20: Madonna
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Love’s gonna lift her up…or not. The Queen of Pop has had plenty of iconic live performances, but this one is remembered for all the wrong reasons. At the 2015 Brit Awards, Madonna closed out the show with a rendition of her song “Living for Love”. Beginning the performance at the top of a flight of stairs, she suddenly ate the ground as her giant black cape billowed behind her. But despite the awkwardness of the fall, we have to hand it to the Queen. She got right back up and recovered remarkably well, living out the song’s empowering lyrics of moving on from your mistakes in style.
#19: Selena Gomez
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Not even Alex Russo could have worked her magic to fix this one. While she’s grown in her abilities in the years since, Selena Gomez’s performance at the 2013 KIIS-FM Jingle Ball wasn’t her finest moment. During her time taking the stage, the former Disney star ran into quite a few roadblocks. Her vocals weren’t at their best, partially due to some behind-the-scenes sound issues, and at the same time she appeared to be lip-syncing without putting much effort into masking it. As Gomez became increasingly frustrated over the technical difficulties, she even dropped the F-bomb in front of her then-young fans. Gotta keep an eye out for that Selener!
#18: Iggy Azalea
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I-G-G-Y? More like, I-G-G-Why? Shortly after Iggy Azalea’s rise to fame, a resurfaced video of her live freestyling at the 2013 Splash Festival did some damage to her credibility. In the viral clip, Azalea spat rapid-fire rhymes in her signature blaccent, even making reference to being a “runaway slave-master.” Besides the overall cringey delivery, the optics of this lyric aren’t great given her much-debated position as a white woman in hip-hop. Somehow the crowd seemed to be just as into it as Azalea, with the performance only blowing up online for negative reasons after the fact. She’s got 99 problems, and they pretty much all showed up here.
#17: The Pussycat Dolls
Top 10 UNBEARABLY Awkward Live Musical Performances
This performance was bursting at the seams with intergroup tension. When the Pussycat Dolls sang “Buttons” at the 2006 American Music Awards, they didn’t even try to hide that behind-the-scenes trouble was afoot. Not only did member Jessica Sutta knock over her chair during the dance routine, but fellow Doll Melody Thornton only came out in the end, giving off the impression of crashing the performance. And while her ad-libs also appeared on “Buttons”’s studio version, they were so over-the-top here that it seemed as though Thornton was intentionally trying to upstage lead singer Nicole Scherzinger — who didn’t look too pleased.
#16: Dua Lipa
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Go girl, give us nothing! It’s hard to imagine in a post-“Future Nostalgia” world, but Dua Lipa wasn’t always known for her onstage electricity. In fact, far from it. Her early lack of live confidence was especially evident at the 2018 Brit Awards, when she performed her breakout hit, “New Rules”. Whether it was the song’s choreography or Lipa’s own energy to blame, the stiff results didn’t necessarily highlight her best attributes. In her defense, she had come from a modeling background and the runway requires a different skill set. Thankfully, the “Don’t Start Now” singer has improved leaps and bounds since, becoming one of pop’s most improved players.
#15: Justin Bieber
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Yeah, he got that yucky, yucky, yucky. During the Glendale, Arizona stop on his 2012 Believe tour, Justin Bieber gave a sick performance of his song “Out of Town Girl”...literally. After getting nauseous, he ran off stage while his backup dancers did their best to keep the crowd hyped amid the chaos. Regardless of your feelings about the Biebz, he shouldn’t be blamed for this moment’s awkwardness. We’ve all been there, even if it didn't happen with tens of thousands in attendance. The then-18-year-old thankfully had a sense of humor about the incident, tweeting the “Anchorman” quote, “Milk was a bad choice.”
#14: Lorde
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Love it or hate it, this performance certainly had no shortage of melodrama. While Lorde isn’t the kind of pop star known for their dancing, that didn’t stop her from doing exactly that at the 2017 VMAs. The singer-songwriter twirled around with reckless abandon throughout her song “Homemade Dynamite,” and most people just didn’t get it. However, there was a method to Lorde’s apparent madness after all — she had the flu which impeded her singing, so she busted out the moves instead. Even if the performance felt out of character, it oddly makes total sense at the same time and has gone down as one of Lorde’s signature moments.
#13: Destiny’s Child
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Okay, ladies, now let’s get in formation. Over a decade before Beyoncé’s acclaimed solo hit, one third of Destiny’s Child struggled to find their footing during a 2004 appearance on “106 & Park.” Just as the trio began their song “Soldier,” Michelle Williams took a major tumble. This wasn’t just your average fall, either: it was loud, looked painful, and her bandmates barely acknowledged the nosedive beyond a simple side-eye. Thankfully, Williams was able to get back on her feet and the show went on without a hitch. The gospel singer has acknowledged the performance over the years, revealing people still bring it up to her weekly, but seems to be a good sport about the embarrassing moment.
#12: Nick Jonas & Kelsea Ballerini
He might have aced Camp Rock but depending on who you ask, he could have spent another summer at Camp Country. At the 2016 ACM Awards, Nick Jonas flubbed a guitar solo during Kelsea Ballerini’s song “Peter Pan.” While he played it off cool, with most viewers likely unable to detect the mistake, Jonas beat himself up about the bum note for years to come. In 2023, he went on the podcast “Armchair Expert,” where he called it a “traumatic moment” for his perfectionist nature. Honestly, this performance seems to be more unbearably awkward for Jonas himself than anyone else.
#11: Lana Del Rey
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This 2012 performance marked one of the few times an artist had performed on SNL before the release of a full album, and the reaction was less than overwhelming. Upon the release of singles ‘Blue Jeans’ and ‘Video Games,’ Lana’s music was said to have cinematic qualities- it was acclaimed by critics and fans alike for her emotive and nostalgic rhythm. However, when she took the SNL stage, our favourite new glamorous indie artist no longer allured audiences with her smoky voice, and was suddenly being slated for her show.
#10: 50 Cent
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When 50 descended on to the stage in Los Angeles to perform his track “Amusement Park”, he severely embarrassed himself. The host spoke for audiences both there and at home when he asked . The founder of G-Unit tries to recover by pretending he just doesn’t care enough to rap the first verse. 50’’s die-hard fans will argue that this was on purpose, or… that maybe he forgot the lyrics, and tried to disguise it by pretending he was going to greet Snoop Dogg with a hi-five. The rapper later admitted the latter, revealing that he couldn’t concentrate after he was unintentionally bumped by a dancer - meaning that the man who was shot 9 times had to once again snap into survivor mode.
#9: Katy Perry & Backpack Kid
This hyperactive popstar has attracted a lot of attention since her hit single “I Kissed A Girl” was released in 2008. One of the more notable moments was this 2017 performance on SNL, which left people laughing uncomfortably. Katy Perry loves to push the latest trends, whether it’s dabbing or attempting the floss dance, a dance move inspired by the Instagram famous “Backpack Kid”. The Backpack Kid was then invited by the singer to perform with her on the show - and he ended up stealing it!
#8: Red Hot Chili Peppers
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It’s not always been plain-sailing for this iconic band. When struggling to deal with their new-found fame, former guitarist John Frusciante developed a drug problem and began to show a lack of passion for the music. Friction between him and lead-man Anthony rocketed at this 1992 SNL gig, with John reportedly almost getting into a fight with one of the crew. Apparently, Madonna was also on set that night and had upset John by blanking him. Anthony has since accused John of deliberately playing badly, and many believe his off-key performance to be a way of trolling his own bandmates.
#7: Fergie
Much like the ones bursting in air, this performance was most definitely a bomb. At the 2018 NBA All-Star Game, the players couldn’t keep a straight face during Fergie’s breathy national anthem rendition. Questionable vocals and undertones aside, the arrangement itself is really what drives this performance over the top. Fergie is most closely associated with pop and hip-hop, so enlisting her to bring a jazzy interpretation to the proceedings doesn’t exactly make sense. She later released a statement to People after it went viral, saying “[It] didn’t strike the intended tone. I love this country and honestly tried my best.”
#6: Mariah Carey
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As we said goodbye to 2016, pop superstar Mariah Carey headlined ABC’s New Year’s Rockin Eve, but her performance certainly wasn’t rockin’ at all. In fact, the New York Post labelled it “disastrous”, with the singer failing to deliver any of the notes to her songs at all. And yet she remained on stage, determined to give some kind of performance. The result... an awkward moment that lasted longer than anyone had hoped it to, leaving fans to shudder their way into the new year. Fortunately, The Songbird Supreme got another chance a year later, and gave it her best shot at redeeming herself.
#5: Kesha
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While Kesha hit fame with breakthrough single “Tik Tok” in 2010, she left SNL audiences shocked and appalled that same year. Her two-song set featured body paint, laser beams and dancing astronauts, which apparently was just too much for some people. Some critics even went as far as calling it “the worst ever.” We guess Kesha’s not for everyone. Not to be deterred, the American singer would release her sophomore record in 2012, and launch a supporting tour the next year.
#4: Miley Cyrus & Robin Thicke
Despite being several years’ old, this one still seems fresh in people’s memory. It would be an understatement to say it raised a few eyebrows. A show that went viral for all the wrong reasons, Miley came out onto the stage twerking and rubbing her foam finger in places we didn’t want to see, and afterwards said that she felt such a sexualised performance had become expected of her. While Cyrus has since changed up her image to a more conservative one, there’s no deny that seeing a former Disney star grind on Robin Thicke’s crotch was very uncomfortable... for everyone.
#3: Ashlee Simpson
It’s debatable whether you can even call this entry a performance, as Simpson’s 2004 “live” set is over almost as soon as it begins. Before she’s about perform her second song, a vocal track for the wrong tune starts to play, so the singer tries to make up for it with a strange dance, before walking off of the stage entirely. After the show, she tried her best to explain herself alongside host Jude Law. But the error was met with huge backlash, and unsurprisginly didn’t do her career any favors. Credit where it’s due though: after Simpson walked off the stage, her band simply carried on.
#2: Corey Feldman
As if he wasn’t already attracting attention for discussing pedophilia in Hollywood, Feldman’s publicity certainly didn’t slow down after this bizarre performance. A long time after he’d starred in films such as “The Goonies” and “Stand By Me”, the child star donned the Today stage in 2006 hoping to promote his new record, and was relentlessly mocked for it. If it isn’t the cringeworthy dance moves or bad vocals that’re unsettling enough, well then it’s the puzzling background of his backing band. Dubbed “the Angels,” they certainly “Go 4 It” with Corey, but we’re not quite sure what “it” is supposed to be.
#1: Britney Spears
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2007 was not the best year for Britney. After checking out of rehab and infamously shaving all her hair off, her performance of then-new single “Gimme More” was difficult to endure. Looking uneasy and self-conscious, it’s clear she didn’t have the right professional help around her at this time, as she came out onto the stage scantily clad and unsure of the lyrics. For a decade, Britney was the princess of pop and was very much in the public eye, with every detail of her personal life making front-page news. Just around the time that her public image was shifting, a lackluster show like this just unfortunately summed up how things were going for her - luckily, she’d bounce back the next year.
