'00s Pop Star Moments That Make Us Cringe

It was the best of times, it was the cringiest of times ... Between frightful fashions and ferocious feuds, the 2000s gave us a variety of meme-worthy moments from its hottest stars. From Britney and Mariah to Eminem and Lil Mama, celebrities from across the industry were not safe from the public-facing disease known as the cringe. Sometimes, it stuck to one star, cycling them through a number of tough public moments over the years. Other times, it would spread itself around a party, latching onto any member it could reach within a star-studded pod. Occasionally, the cringe would strike so hard on one single celebrity within a moment so big and so shudder-inducing that its impact was feared to last forever. As this feature shows, people were right to be afraid, since we're still chatting about these moments today.

While the cringe has since moved on to the greener pastures of social media apps, where infamy can be intense but fleeting, the memories that these embarrassing '00s pop star moments left behind have remained ingrained in the pop culture zeitgeist ever since. 

Mariah Carey's Sweet TRL Surprise

Mariah Carey was already a legendary diva before she made her now infamous appearance on MTV's "Total Request Live." But it was her unexpected sweet treat on a 2001 episode of the iconic show that catapulted her to a new level of stardom — tabloid fodder. At the time, Carey was promoting her single "Loverboy," taken from her soon-to-be film flop, "Glitter." During the episode, she surprised the audience and host, Carson Daly, by revealing a skimpy outfit change before wheeling out an ice cream cart and divvying out treats to the screaming fans. A week later, Carey was hospitalized and put on psychiatric care, per Billboard. It was later revealed that she had been diagnosed with bipolar disorder.

In a 2020 episode of "Watch What Happens Live," the singer told Andy Cohen that the incident had been blown out of proportion. "By today's standards, it's like nothing," she said. "... I look at it now and I'm like, 'Oh please!' They acted as if I had stripped butt naked on TV." She added that at the time she was struggling to maintain control over her career. Less than a year later, she was dropped by her record label, EMI. In her memoir, "The Meaning of Mariah Carey," the star recalled the full impact of the incident, writing, "All performers bomb, but my bombing set off a chain reaction that placed a target on my back."

If you or someone you know needs help with mental health, please contact the Crisis Text Line by texting HOME to 741741, call the National Alliance on Mental Illness helpline at 1-800-950-NAMI (6264), or visit the National Institute of Mental Health website.

Britney and Justin's Denim Dream

The pop star it-couple of 2001 was undoubtedly Britney Spears and Justin Timberlake. The twosome was featured in tabloids galore, but it was one appearance in particular that made their short-lived coupledom last a lifetime. Spears and Timberlake made waves at the 2001 American Music Awards in a double denim ensemble that has continued to turn heads and drop jaws for decades. Speaking about the inspiration behind the ensemble, costume designer, Steven Gerstein told Jezebel, "It was just two kids, wanting to do something cool, and being super cute, matching. It was kind of like their prom."

According to Gerstein, the couple came up with the idea to wear matching double denim outfits at the event. From there, he enlisted his team in finding 50 or so pairs of vintage Levi's jeans, hired a 24-hour seamstress to put the ensembles together, and whipped up a legendary red carpet moment in no time at all. "It went from being an idea to it being made within days," Gerstein said. "The rest is history."

The look became synonymous with '00s fashion, for both good and not-so-good reasons. Regardless of the public's ire, the ensemble has remained at the forefront of award show moments. It even inspired Katy Perry and Riff Raff to take their own spin on it at the 2014 MTV Video Music Awards.

Janet and Justin's wardrobe malfunction

Justin Timberlake has had more than his fair share of awkward millennial moments, but his taboo performance with Janet Jackson at the 2004 Super Bowl XXXVIII may take the cringey cake. The so-called Nipplegate moment was so shocking that it even coined a new term — wardrobe malfunction. Millions of people watched as Jackson led the Super Bowl XXXVIII Halftime Show at the then Reliant Stadium in Houston, Texas. Timberlake appeared mid-set for a surprise duet of his hit single, "Rock Your Body." He then pulled a tear-away section of Jackson's corset, revealing her right breast on live television while crooning the line, "Gonna have you naked by the end of this song."

Much has been said and reported about the origin of the incident. Was it planned? Did it go too far? By the time the performance ended, the Federal Communications Commission (FCC) was already nipping at the heels of all involved in the show. Former FCC commissioner Michael Powell recalled to USA Today,  "People were falling all over themselves to announce their outrage and their discontent." The FCC eventually fined CBS, who broadcasted the Super Bowl that year. As noted by The New York Times and many other outlets since, while Jackson's career notably took the hit for the incident, Timberlake's did not. In 2021, on Instagram, he apologized to her for reaping the benefits of a system that had seemingly condemned her for the same act.

Kelly and Nelly's texting dilemma

Eagle-eyed viewers caught on to a texting snafu in Nelly and Kelly Rowland's 2002 smash, "Dilemma." What resulted is a meme-worthy moment that even the artists themselves couldn't explain. In the music video for the song, Rowland is lounging at her window, and texting her on-screen beau. The camera cuts to an incoming text message, except it's not a standard messaging screen that it shows — it's an Excel spreadsheet. Cue the confusion ... and the jokes. 

The brow-furrowing chaos has continued for more than two decades, which is the amount of time it took for Rowland to respond to the now iconic video moment. "I don't know what that is," the former Destiny's Child member shared on a 2019 episode of "The Real." "I don't know what Microsoft Excel is ... I don't have a clue." Microsoft Excel themselves even took the time to respond to Rowland's unknowing diss on Twitter, by referencing a "Dilemma" lyric, writing, "No matter what you do, we're crazy over you."

Meanwhile, Nelly had a different take on the use of Excel in texting matters during an appearance on "The Project." "That was the new technology at the time!" he joked. "It looks a little dated now." Years later, some tech-savvy internet users have even kind of solved the mystery of Excel's communication capabilities – a dilemma that may not have been debated if not for ... well, "Dilemma."

Jessica Simpson's tuna confusion

It was the faux pas heard around the world. In a 2003 episode of MTV reality show "Newlyweds: Nick and Jessica," pop star Jessica Simpson took a bite of her mystery meat meal and asked her then-husband, Nick Lachey to clarify what animal was in her meal. "Is this chicken what I'm having or is this fish?" she asked him during the episode. "I know it's tuna, but it says Chicken by the Sea?" Lachey, in turn, stared blankly at his then-wife, before confirming that the meat was indeed tuna and that the brand is Chicken of the Sea.

The result of this iconic reality TV moment? Simpson became branded as the new millennium's dumbest dumb blonde by the media, a stereotype that arguably haunted her career throughout the 2000s. Justin Timberlake even mocked the star's rumored lack of intelligence during a brutal impersonation of her on "Saturday Night Live." The singer-turned-designer has since poked fun at the moment several times on social media. In 2017, for instance, she shared her sympathies with Whole Foods after a report suggested that the store had sold a chicken salad that actually contained tuna. "It happens to the best of us," she quipped on Twitter.

Ashlee Simpson's lip-syncing stint on SNL

While her big sister was hemming and hawing about tuna versus chicken, songstress Ashlee Simpson was busy shimmying her way off stage after a lip sync mishap on "Saturday Night Live." Simpson was supposed to perform the title track from her debut album, "Autobiography." But right after host Jude Law introduced the performance, the vocal track for "Pieces of Me," the song she'd performed earlier in the show, started playing instead. After some shame-induced dancing, she retreated side stage and to viral infamy evermore. 

A week later, Simpson made an appearance on MTV's "TRL," and claimed that she required a vocal track due to a severe case of acid reflux having damaged her voice. She added that her father and manager, Joe Simpson, requested that she use the backing track on the advice of doctors. "It [was] so embarrassing because it sucks," she said. "The total situation was a bummer. I made a complete fool of myself." She had previously denounced lip-syncing during an interview with Lucky Magazine (via MTV), stating, "I'd never lip-synch. It's just not me."

The moment went on to be widely parodied, and the singer went on to change her tune on the situation years later. "I should have said 'No, I will not go on, I will not do this,'" she reflected to Andy Cohen on "Watch What Happens Live" in 2018. "...[But] it made me stronger. S*** happens."

That time Fergie black-eyed-peed her pants

In 2005, the Black Eyed Peas were everywhere. The group's "Monkey Business" album was topping charts left and right, and their singer, Fergie, was on her way to icon status. But during a performance in San Diego that year, the star got the show started by urinating herself on stage. One concertgoer snapped a picture of the wee incident and the rest was history. It became an all-out meme, with the picture being displayed on news outlets, computer screens, and even homemade mugs years after the event took place.

"I'm running on and we jump and do 'Let's Get It Started', and I get crazy and I jump and I run across the stage and my adrenaline was going and gosh," she revealed in an interview on Hot97 (via Daily Mail). "I wish it didn't happen ... It was so embarrassing!"

But not everyone was making fun of Fergie. In fact, the incident even garnered respect in some circles. In a 2015 op-ed for Vice, writer Dan Ozzi jokingly reflected that there was some credibility owed to a singer so hyped for a tune that she pees herself during its performance. "Fergie suffered for her art," he lamented. "The next time you're thinking of making a joke at Fergie's expense to the tune of her peeing in her pants, just remember: She did it for you."

Fergie's free-styling stage antics

Fergie has got quite the reputation when it comes to stage presence. Even if she's not peeing her pants mid-performance, she knows how to command a stage, and capture attention, in any way she can. In 2008, the singer performed a cover of Heart's "Barracuda" on "The Today Show." As the song reached its crescendo, Fergie channeled her inner cheerleader and began doing front flips, microphone in hand, while singing. The footage instantly went viral and sent the songstress tumbling into the Twittersphere and people's subconsciousness. Years later, she commented on an Instagram post reliving the moment, by responding, "My signature dance move."

However, her most infamous moment was her questionably jazzy rendition of the National Anthem at the 2018 NBA All-Star Game. Her unusual take on the tune was not well received, and even the NBA players on the sidelines couldn't help but laugh during the performance. In fact, the backlash got so bad that even Fergie's ex-husband, Josh Duhamel, publicly spoke in defense of her and suggested that Golden State Warriors forward, Draymond Green, owed her an apology. After the team enjoyed a locker-room dance-off to a remixed version of her performance, the issue appeared to be resolved, and in good humor, per NBC Sports.

Ultimately, it was Fergie herself who had the last word. "I'm a risk taker artistically, but clearly this rendition didn't strike the intended tone," she told TMZ. "I love this country and honestly tried my best."

Britney's lackluster comeback performance

Britney Spears faced her own share of troubles in the mid-aughts before making her big "comeback" at the 2007 MTV Video Music Awards. Donned in a black bra and panty set with calf-high boots, Spears performed her latest single at the time, "Gimme More" with less than her usual zeal. Her straight-faced on-stage performance matched the audience's unmoving expressions, while millions watching at home were equally stunned. 

Spears has never openly discussed the performance, but that hasn't stopped speculation as to why the lackluster and frankly troubling moment happened. "She was just plain nervous because of all the hype and she's embarrassed," one source told People. Another added, "It's been a while since she's done this, and she was performing in front of all her peers, on live TV. She just got out there and froze."

If that wasn't enough, the media were quick to comment on the shocking performance. But leave it to the fans who make up her Britney Army and even her backup dancers to come to Spears' defense — especially after footage of the decidedly more enthusiastic rehearsal footage was shared online. "[We] put a lot into that performance because it was [Spears'] first time back in a while," dancer, Aminah Abdul Jillil told Vice. "I would have to say out of all of [the VMA performances] that was my favorite one."

When Eminem received a fallen angel fanny facial

In 2009, Eminem got quite the unique facial at the MTV Movie Awards courtesy of an angelic, Sacha Baron Cohen. The provocative British comedian was in character as Bruno from his film of the same name. He entered the show on a harness, flying through the crowd when he suddenly fell upon a seemingly unknowing Eminem and his entourage. What made the situation worse is that Bruno was wearing a jockstrap and nothing more, meaning his bare behind landed in the rapper's face. Visibly unamused, he and his crew stormed from the audience while the fallen angel was forcibly removed. 

Per the New York Post, the risqué stunt was confirmed to be pre-planned and presumably played upon accusations that Eminem had been homophobic in his lyrics — allegations he's continuously denied. Speaking to RapRadar, the "8 Mile" star confirmed he was in on the gag. "Sacha called me when we were in Europe and he had an idea to do something outrageous at the Movie Awards," he explained. "I'm a big fan of his work so I agreed to get involved with the gag." Baron Cohen, for his part, has not commented on the stunt.

So what happened in the shady aftermath of it all? "After the ceremony, I went back to my hotel and laughed uncontrollably for about 3 hours, especially after I saw it on air," he revealed. Sounds like Eminem put his Oscar to good use.

Lil Mama Crashed Jay Z and Alicia Keys' Stage

The MTV Video Music Awards are known for their outrageous antics and unforgettable moments, but the 2009 show had some of the most memorable so far. When Jay-Z and Alicia Keys were performing their smash single "Empire State of Mind," the duo had a surprise celebrity stage-crasher in the form of rapper, Lil Mama. Keys herself was pretty surprised from the get-go — in fact, she wasn't even aware it had happened."The whole show, I was so focused on making it amazing," Keys shared on the "Drink Champs" podcast in 2021. "I went backstage and Jay was like 'You ain't see that?!'"

During a Twitter Spaces interview (via Complex), Jay later spoke about the incident himself and shared that he was now cool with Lil Mama having crashed the performance party. "She's a New Yorker... She got excited. Things happen," he said. "Of course we love her ... Yes, she's forgiven." Once she heard of her idols' comments years after the fact, Lil Mama gave her own statement thanking them for their grace. "Love for both my big brother, big sister, and my city," the rapper shared (via Complex). "It brings clarity to all of us as a community to actually hear these words from our legendary leaders."

Kanye interrupts Taylor Swift's VMA speech

One of the most iconic pop culture moments for all the wrong reasons of the '00s involves a pop star, a rapper, and a stolen microphone. At the 2009 MTV Video Music Awards, Kanye West stormed the stage and stole Taylor Swift's microphone mid-speech. The rapper voiced his opinion that Beyonce, who was nominated in the same category that Swift won in, should have taken the award home instead. From there, "Imma let you finish" became a household phrase, beleaguered meme, and permanent fixture in 2000s pop culture history. 

Much has been said about this incident, and the on-again-off again-very off-again frenemies have traded words, songs, and Instagram posts ever since. But leave it to Beyoncé to turn the cringe of all cringes into something better. Later that night, the "Renaissance" star took to the stage to accept an award and turned the mic back over to Taylor, so she could finish her acceptance speech. "I remember being 17 years old, up for my first MTV Award with Destiny's Child, and it was one of the most exciting moments in my life," she shared with the audience. "So, I'd like for Taylor to come out and have her moment."

It's a reprieve that few seem to remember but it still made an impact. Beyoncé went on to be ... well, Beyoncé. And the ensuing feud between West and Swift continued to rattle on for well over a decade.