From bladder control issues to infamous private parts to bizarre texting habits,
these are the pop star moments that had us cringing in the 2000s.
The It Couple of the early 2000s were undoubtedly Britney Spears and Justin
Timberlake. They really made waves at the 2001 American Music Awards in a double
denim ensemble that has continued to turn heads in the years since.
Costume designer Steven Gerstein enlisted his team to find 50 or so pairs of vintage Levi's jeans,
hired a 24-hour seamstress to put the outfits together, and then whipped up
a legendary red carpet moment in no time at all. As he noted to Jezebel in 2020,
"It went from being an idea to it being made within days. The rest is history."
The look has since become synonymous with early '00s fashion, for both good and ill. It even
inspired Katy Perry and Riff Raff to offer their own spin on it at the 2014 MTV Video Music Awards.
Justin Timberlake has had more than his fair share of awkward moments, perhaps none more so
than his 2004 taboo performance with Janet Jackson at the Super Bowl XXXVIII Halftime Show. So-called
Nipplegate was so shocking that it even led to the coining of the term "wardrobe malfunction."
Timberlake appeared in the middle of Jackson's set for a surprise duet of his hit single,
"Rock Your Body." He then pulled off a tear-away section of Jackson's corset,
revealing her right breast on live TV for millions of viewers at home to see.
By the time the performance ended, the Federal Communications Commission
was already nipping at the heels of all involved in the show. In 2018,
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, which aired the game that year. Jackson's
career notably took a hit in the aftermath, while Timberlake emerged mostly unscathed. In 2021,
he apologized to her on Instagram for reaping the benefits of a system that had condemned her.
Eagle-eyed viewers caught on to a texting snafu in Nelly and Kelly Rowland's 2002
smash hit song "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 seen lounging
at her window and texting her on-screen beau. The camera cuts to an incoming text message,
except that what's shown isn't a standard messaging screen, but rather an Excel spreadsheet.
The scene resulted in some brow-furrowing chaos that has lasted for more than two decades,
which is the amount of time it took for Rowland to respond to this now-iconic
moment. She eventually addressed the uproar on a 2019 episode of The Real.
"I don't know what that is. I don't know what
Microsoft Excel is. I don't know. I don't have a clue."
The Microsoft Excel social media team then responded to the talk
show clip by referencing a "Dilemma" lyric by tweeting,
"No matter what you do, we're crazy over you."
Meanwhile, Nelly offered a different take on the
matter when he appeared on the Australian show The Project.
"That was a new technology at the time! I mean,
it, it looks a little dated now. Yeah, I can see it."
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."
In a 2003 episode of the MTV reality show Newlyweds: Nick and Jessica, pop star Jessica
Simpson asked her then-husband Nick Lachey to clarify what animal she was eating. As she put it,
"Is this chicken what I'm having or is this fish?"
"I know it's tuna, but it, it says Chicken… by the Sea. Is that stupid?"
Lachey stared blankly at his wife, before confirming that the meat was indeed tuna
and that Chicken of the Sea was just the brand name. Simpson subsequently
endured a reputation as the era's dumbest dumb blonde, a stereotype that's arguably haunted
her career ever since. Fellow pop star Justin Timberlake even mocked her supposed lack of
intelligence with a brutal impression on an episode of Saturday Night Live.
"You may call me stupid. You may even call me dumb. But think about this."
Simpson has since poked fun at the moment several times. 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. As she quipped on Twitter,
"It happens to the best of us."
While her big sister was pondering about fish and poultry, Ashlee Simpson was busy shimmying her way
off stage after a very public mishap on Saturday Night Live. She was supposed to perform the title
track from her debut album, Autobiography. But right after host Jude Law introduced her,
the vocal track for "Pieces of Me," the song she'd performed earlier in the episode, started playing
instead. After some awkward impromptu dancing, she retreated off the stage and into viral infamy.
A week later, Simpson stopped by MTV's Total Request Live and claimed that she required a vocal
track due to a severe case of acid reflux damaging her voice. She added that her father and manager,
Joe Simpson, requested that she use the backing track on the advice of doctors.
The moment went on to be widely parodied,
and Simpson herself would offer up a somewhat different explanation years later,
as she addressed the incident during a 2018 episode of Watch What Happens Live.
"And I should have said 'No, I will not go on, I will not do this.'"
"For me it made me stronger, and you know, s— happens."
In 2005, the Black Eyed Peas were everywhere. Their Monkey Business album was topping the
charts left and right, and Fergie was on her way to becoming an icon. But
then something rather embarrassing happened. During a performance in San Diego that year,
the singer got the show started by peeing in her shorts while on stage. The moment became
the stuff of memes, with a photo of the incident appearing on news reports, computer screens,
and even homemade mugs. During a 2014 interview on Hot 97, Fergie admitted,
"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. I wish it didn't happen. It was so embarrassing!"
"Can we stop? This is horrible. This is the worst."
And that wasn't the only time that Fergie caught our attention for more than just
her singing. In 2008, she performed a cover of Heart's "Barracuda" on The Today Show.
Fergie channeled her inner cheerleader and began doing front flips with her microphone in hand,
and the footage instantly went viral.
But Fergie's most infamous moment was surely her questionably jazzy rendition of the National
Anthem at the 2018 NBA All-Star Game. Even the players on the sidelines couldn't help but laugh
during the performance. The backlash was so bad that Fergie's then-husband, Josh Duhamel,
publicly spoke in defense of her and suggested that Golden State Warriors forward Draymond Green
owed her an apology. Ultimately, it was Fergie herself who had the last word, as she told TMZ,
"I'm a risk taker artistically, but clearly this rendition didn't
strike the intended tone. I love this country and honestly tried my best."
Britney Spears faced her fair share of troubles in the mid-2000s before attempting to make a
big comeback at the 2007 MTV Video Music Awards. Donned in a black bra and panty set
with calf-high boots, she performed her latest single, "Gimme More" with less than her usual
zeal. Spears has never publicly discussed the performance, but that hasn't stopped
speculation about what exactly happened. As one source claimed to People Magazine,
"She was just plain nervous because of all the hype and she's embarrassed."
Meanwhile, another source explained,
"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."
In response to the blowback, Spears' backup dancers and fans came to her defense,
especially after footage of some decidedly more enthusiastic rehearsal footage was
shared online. As dancer Aminah Abdul Jillil told Vice in 2016,
"[We] put a lot into that performance because it was her first time back in a
while. I would have to say out of all of [the VMA performances] that was my favorite one."
One of the most unforgettable pop culture moments for all the wrong reasons is surely
the time at the 2009 MTV Video Music Awards when Kanye West stormed the stage and stole
Taylor Swift's microphone mid-acceptance speech. Swift had just won Best Female Video for "You
Belong with Me," and West proclaimed his opinion that Beyoncé should've won instead. His utterance
of "Imma let you finish" has since become a permanent fixture in 2000s pop culture history.
"I have met Kanye, and I am incapable of being surprised by him."
West and Swift have traded words, songs, and Instagram posts ever since. But what's
often lost in the historical retelling is that later that night when Beyoncé took to
the stage to accept an award, she turned the mic back over to Taylor so that she
could finish her acceptance speech. As the "Single Ladies" singer put it,
"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. So I'd like for Taylor to come out and have her moment."
Eminem got quite the too-close-for-comfort greeting at the 2009 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 unsuspecting Eminem and his entourage.
What made the situation worse is that Cohen was wearing a jockstrap and nothing more,
meaning his bare behind landed in the rapper's face. Visibly unamused,
Eminem and his crew stormed from the audience while the fallen angel was forcibly removed.
Eventually, the stunt was confirmed to have been planned ahead of time,
presumably playing upon accusations that Eminem had been homophobic in his lyrics,
something he's continuously denied. As the rapper revealed to RapRadar,
"Sacha called me when we were in Europe and he had an idea to do something outrageous at
the Movie Awards. I'm a big fan of his work so I agreed to get involved with the gag."
Baron Cohen hasn't publicly commented on the stunt, though Eminem also added,
"After the ceremony, I went back to my hotel and laughed uncontrollably for about 3 hours,
especially after I saw it on air."
Mariah Carey was already a legendary diva when she made her infamous 2001 appearance on Total
Request Live. At the time, she was promoting her new single "Loverboy," off the soundtrack to her
movie Glitter. She surprised host Carson Daly by wheeling out an ice cream cart and divvying
out frozen treats to the screaming fans. A week later, Carey was hospitalized and
put on psychiatric care. It was later revealed that she'd been diagnosed with bipolar disorder.
During a 2020 episode of Watch What Happens Live,
Carey insisted that the incident had been blown out of proportion.
"By today's standards, it's like nothing."
"I look at it now and I'm like, 'Oh please!' They acted, like,
as if I had, liked, stripped butt naked."
Carey 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,
she recalled the full impact of the incident, as she wrote,
"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.