Awkward Grammys Moments Caught On Camera

The Grammy Awards stage is no stranger to unexpected and incredibly awkward moments that just have a way of unfolding during live televised events. At the Grammy Awards, where musical excellence collides with the unpredictability of live television, some of the most enduring memories are not necessarily the triumphs of the stars but the cringey moments and faux pas that punctuate the performances, announcements, and winning speeches. Over the years, the Grammys has become a platform for unscripted brilliance and unexpected turns that have etched themselves into the annals of pop culture history.

The embarrassing moments — from a surprise storming of the stage during a performance to an artist mishearing the winner's name to a star even tripping on stage – have become almost more iconic than the music that graces the Grammy stage and the winners who take home their awards. Here is a look back at some of the most awkward Grammy moments ever.

In 1998, Michael Portnoy, also known as the "Soy Bomb guy," created a viral moment before viral moments existed. The New York-based performance artist made a splash during Bob Dylan's performance of "Love Sick." Cast as a background dancer for the performance, Portnoy seized the opportunity to make a statement. Tearing off his shirt, he revealed the words "Soy Bomb" scrawled across his chest and started to awkwardly dance. Reflecting on the incident 25 years later, Portnoy stated in an interview with Mojo 4 Music, "I knew I had to do some kind of intervention."

Dylan's guitarist, Larry Campbell, recounted the singer turning to him and asking, "Who the hell is this guy?" Lasting some 35 seconds before security intervened, Portnoy's act became the defining moment of the night.

The intentional choice of the words "Soy Bomb" represented Portnoy's concept of "dense, transformational, explosive life," The Hollywood Reporter revealed. Despite its brevity, the incident was witnessed by an estimated 20 million viewers, leaving an enduring mark on Grammy viewership. Portnoy told the outlet that he aimed to "inject some confusion into the mainframe." Additionally, because there had only been one rehearsal, the crew wasn't sure whether the moment was planned, leading Portnoy to secretly hope, "'F***, someone please take me off stage.'" Despite being escorted offstage and onto 50th Street in the dead of winter, the "Soy Bomb guy" left an indelible legacy on the Grammy Awards and definitely lives in the Awkward Moment Hall of Fame.

In 2004, the Super Bowl XXXVIII halftime show became infamous for the "Nipplegate" incident when Justin Timberlake caused Janet Jackson to have a "wardrobe malfunction" that exposed her breast, leading to widespread public outcry. At the Grammy Awards the following week, Justin Timberlake found himself issuing a formal apology in the middle of his acceptance speech. However, it wasn't merely a gesture of politeness. CBS revealed in a statement that it had "serious reservations" about inviting the "Cry Me a River" singer to the event. The apology turned out to be a condition imposed by the Recording Academy for both singers' appearances on the show. According to the statement, "Ms. Jackson declined the invitation. Mr. Timberlake accepted."

The aftermath of "Nipplegate" had repercussions for both artists, though Jackson appeared to bear the brunt of the fallout. She faced professional setbacks, and Timberlake, who was criticized for not supporting Jackson, was subject to the public's anger.

In his Grammy acceptance speech for Best Male Pop Vocal Performance for "Cry Me a River," Timberlake awkwardly addressed the audience. "Listen, I know it's been a rough week on everybody," he said (via CNN). "What occurred was unintentional and completely regrettable, and I apologize if you guys were offended." He added that winning a Grammy had been his dream, saying, "This is officially the greatest moment of my life." Yikes.

Even global sensations like Taylor Swift can experience awkward moments. In 2014, Swift's album "Red" was nominated for the Album of the Year at the Grammys, competing against Daft Punk's groundbreaking "Random Access Memories." When "Random Access Memories" was announced as the winner (with a very prolonged Rr-random), Taylor thought — just for a moment — that she had clinched the award. And at the end of the day, you can't really blame her. The supporters sitting beside Swift also clearly thought that she had won. Unfortunately for the singer, the awkward moment, first showing her triumph and then her swift recovery, was caught on camera.

It seems that Swift took the disappointment of losing rather hard. In an interview with Grammy Pro, the singer-songwriter said, "I went home, and I cried a little bit, and I got In-N-Out Burger and ate a lot" (via Entertainment Tonight). Swift also took the moment as an opportunity to fuel her creative fire rather than allow it to dishearten her. "You have a few options when you don't win an award," she told Grammy Pro. "For one, you can decide like, 'Ugh, they're wrong. they all voted wrong.'" Or, Swift said, "'You can say, 'Maybe they're right.'" Swift went on to release 1989 later that same year, which won multiple Grammys, including Album Of The Year. 

On the red carpet for the 2015 Grammy Awards, Taylor Swift found herself in an awkward exchange with an Entertainment Tonight reporter who asked an ill-judged question about the singer's love life. By today's standards, especially, the interview was shocking as the main focus was on objectifying Swift and talking about men at a time when the singer was being especially judged for matters in her personal life. The interviewer asked the camera to pan down on Swift's dress, saying, "I just wanted to show the legs" – something that clearly made the "Anti-Hero" singer uncomfortable. 

The interviewer followed up this awkward moment by adding insult to injury, suggesting that Swift would "walk home with more than maybe just a trophy tonight, I think, lots of men." In a firm and direct response, Swift refuted the reporter's assumptions, saying, "I'm not going to walk home with any men tonight. I'm going to go hang out with my friends, and then I go home to the cats. ... Men get me into trouble!" This candid and humorous reply not only deflected the awkwardness but also reinforced Swift's ability to handle such situations with grace and wit.

Taylor Swift's exuberant award-show dance moves are as iconic as her chart-topping hits. However, at the 2015 Grammy Awards, her lively groove session made for a very awkward viral moment when Pharrell Williams shot her a bemused and seemingly unimpressed look. Caught in a moment of disbelief, his side-eye sparked a flurry of comments and memes across social media platforms. This was right at the time that the whole world seemed to be turning against swift, so the tweets responding to the moment were particularly vitriolic.

One X (formerly Twitter) user wrote, "The only thing that [Pharrell] has going for him is his side eye to [Taylor Swift] dancing #ThankYou" (via Daily Mail). Another wrote, "Im gonna need Taylor Swift to calm down in the front row. Act like you've sat there before, doll." Perhaps it's no coincidence that Swift later released the song "You Need to Calm Down."

Fortunately for Swifties and Swift's iconic dance moves, the singer's resilience and carefree attitude prevailed. She continued to dance away at subsequent award shows. As evidenced by her lively moves at the 2023 VMAs, Taylor Swift remains unapologetically herself, turning each award show into her own dance floor.

At the 58th Annual Grammy Awards, Tori Kelly looked unimpressed during Taylor Swift's headline-making Album of the Year acceptance speech on February 15, 2016. The "Should've Been Us" singer found herself in the spotlight, caught on camera with the expression as Swift claimed her second Album of the Year award. As this was a time when the internet was turning against Swift, Kelly's reaction became a massively viral moment.

Twitter users were quick to comment, with one user saying, "Tori Kelly real for making this face during Taylor Swift's speech. Shout out to her" (via Us Weekly). Another tweet suggested, "When you're not feeling #1989 and wanted #ToPimpAButterfly to win #AlbumOfTheYear." Despite the apparent skepticism captured on camera, Tori Kelly took to Twitter to assure fans that she had a great time at the event and harbored no ill will. "I loved every moment of last night," she wrote. "I can't express how thankful I am. Here's to the next chapter." The moment just goes to show that the awkward moments the audiences perceive may not always mean what they think they do.

On February 12, 2017, the Grammy Awards witnessed an extremely uncomfortable moment when the band Twenty One Pilots, comprising Tyler Joseph and Josh Dun, clinched the Grammy for Best Pop Duo/Group Performance for their hit "Stressed Out." As the duo rose to accept the prestigious award, they astounded viewers by shedding their pants and striding towards the stage in nothing but their underwear.

In a 2021 interview with Zane Lowe for Apple Music, Tyler Joseph revisited the infamous decision, saying, "I cannot believe we did that. I don't know what we were doing" (via Bustle). However, the Joseph revealed the basis for the decision in the acceptance speech. "As we were watching [the Grammys] we noticed that every single one of us was in our underwear. ... Josh turned to me — and we were no one at that time ... he said, 'If we ever go to the Grammys, if we ever win a Grammy, we should receive it just like this.'"

Joseph explained to Lowe that he sees the moment as a symbol of the strength of his friendship with Dun. "I do think that the most amazing part of that story is the confidence and the security in my friendship with Josh that I would take my pants off first, I'd start walking, and I knew he was standing behind me with his pants off," he said.

The Jonas Brothers gave an amazing performance at the 2020 Grammy Awards. Unfortunately, that wasn't what the internet remembered — because it just so happened that Nick Jonas had a little something stuck in his teeth.

In a candid revelation on "The Tonight Show Starring Jimmy Fallon," Nick humorously revealed what happened. "So, here's the thing that's really frustrating about this, okay? Is that, first of all, there was spinach in my teeth from my breakfast, which I ate hours before," he confessed. In an interview for Capital FM, the singer recounted exactly what was stuck in his teeth, saying, "I had what I have every day for breakfast — egg white omelet, spinach, mushrooms, a little bit of feta cheese." To add a layer of irony, his bandmates, Joe and Kevin, made sure to check each other's teeth before heading out on stage, but Nick was apparently left out.

Nick shared with Jimmy Fallon that his manager tried to keep away from his phone after the performance, telling him, "You had a little something in your teeth." Sure enough, he had a text message from Adam Levine waiting for him. "He's like, 'Nice performance. You had a little schmutz in your teeth,'" Nick recounted. Not even pop stars are immune to embarrassing moments.

this is sending me #Grammys pic.twitter.com/EQJJatj5Eg

— Wendell (@RhodeToLove) February 5, 2023

The internet was once again set ablaze in 2023 when Myles Frost, an American actor and dancer known for playing Michael Jackson in Broadway's "MJ the Musical," announced Harry Styles' Grammy win with significantly less gusto than that with which he announced other winners' names. Frost presented several awards at the Grammys premiere ceremony, which was streamed online. Unfortunately for Frost, his contrasting reactions while announcing winners quickly caught the internet's attention.

A compilation video circulating online showcases Frost's markedly subdued declaration of Harry Styles' victory compared to his more animated and enthusiastic announcements for Beyoncé and Lizzo's wins. At the ceremony, Lizzo earned a Grammy for Best Remixed Recording, Beyoncé won Best Dance/Electronic Recording and Best Traditional R&B Performance, and Harry Style took home the Grammy for Best Engineered Album, Non-Classical. Frost's awkward moment left some viewers confused and others amused.

‘Harry does fall a lot on stage!’ 😂 pic.twitter.com/92niSH8p7K

— Erin 🫧 (@4everfolklore) February 6, 2023

Myles Frost's unenthusiastic announcement of Harry Styles' win for Best Engineered Album, Non-Classical, was not the only awkward Grammys moment for Styles. Styles, known for his charismatic stage presence, nearly fell during his Grammys performance in 2023. The pop superstar was confidently striding across a raised rotating platform while singing "As It Was" from his acclaimed album "Harry's House," which had earned multiple nominations at the 65th Grammys. As Styles navigated the rotating stage with characteristic energy, he lost his balance, prompting a quick arm gesture to steady himself. Fortunately, the musician swiftly regained his composure and continued the performance, reaching the microphone to finish the song without missing a beat.

Despite the incident being a fleeting blip in his overall performance, the moment didn't escape the watchful eyes of fans and the ever-vigilant social media community. The incident sparked a flurry of reactions online, with fans expressing a mix of concern, relief, and humor. One fan wrote on X (formerly Twitter), "When Harry jumped back on the spinny thing I did in fact scream DONT FALL" (via StyleCaster).