Total Request Live is the reason we rushed home from school every day throughout middle school and high school. The iconic show, which premiered in 1998 and was hosted by Carson Daly, quickly became must-see afternoon TV for an entire generation of music lovers.
This was especially because since MTV often had the latest and hottest boy bands and pop singers — including The Backstreet Boys, NSYNC, Britney Spears, Christina Aguilera, and Destiny's Child — on as special guests and performers. The show was also the place to catch the world premieres of brand-new music videos. Yes, this was long before you could watch every new music video on YouTube whenever you want!
TRL totally set the tone for pop music at the time, and some might even say it's responsible for helping hip-hop, rap, alt-rock, and other controversial musical genres go mainstream. Beyond the music, TRL was our first glimpse at emerging fashion and beauty trends, and most of us would flock to the mall to see if we could find clothing, accessories, and makeup that would help us look more like our favorite music stars.
That said, TRL's heyday was the early 2000s, which in retrospect was a really iffy era in fashion. It was all about over-accessorizing, wearing as much glitter and sparkle as possible, and mixing and matching patterns, fabrics, and styles that painfully clashed. The celebrities we saw on TRL were the style guinea pigs, and they'd show up to the set in outfits that we find beyond cringeworthy when we look back on them.
Keep scrolling and get ready for a blast from the past when you see some of these questionable looks.
Jewel
Jewel was never really a pop star. She's a folksy singer-songwriter with a beautiful voice that people love, but when she showed up to TRL one day in 2003, wrapped in a pink bow, it was clear she was trying hard to make a crossover into the pop world. It just looked silly and inauthentic.
Destiny's Child
It's true that as an all-girl pop group, Destiny's Child mostly wore stage costumes to both appearances and shows, and to be honest, a lot of their matching outfits were absolutely wild. For a time, Beyoncé's mom designed all of their looks. But these belly-baring, western-inspired getups were out of control. The sparkly cowboy hats with blue bandanas were way too much.
Gwen Stefani
At the time of this 2004 TRL appearance, Gwen Stefani — who has always been a fashion risk-taker — was a relatively new solo artist and she was definitely experimenting with her style and trying to make a break from the punk-rock roots she had established with her band, No Doubt. We're used to seeing pretty wild outfits from her, but this one takes the cake. That whole cuffed denim, leg warmers, and stilettos situation is quite an eyesore.
Tyra Banks
Tyra Banks is a model and TV star — there is absolutely no reason for her to wear something so ridiculous. None of these styles go together — not the dress, the vest, the shoes, or the jewelry, but if she just took that vest off, she would've looked so much better. Also, why was she wearing resortwear sandals with menswear?
Raven-Symoné
We adored Raven-Symoné on the Disney Channel series That's So Raven. Her character often wore really bold outfits. It worked on a fictional show; it did NOT work on TRL. There was so much going on here. The matching earrings and necklace and that ruffled skirt look like something a hippie grandma would wear.
Mya
Mya is gorgeous, and we really love her hair and makeup here, but this outfit is all kinds of wrong. A tutu-style plaid skirt with a super-tight tank top emblazoned with words too shiny to even read?! It's a no for us. She should have worn some cute jeans and heels with that tank, and saved the skirt to pass down to a toddler.
Taryn Manning
We don't get it! What was this outfit on Taryn Manning? Where was her shirt? We can't tell if that's a bra under there or something else. Taryn looked like a drunk politician getting home after a late event from the waist up, and a punk rocker from the hips down. It's all very confusing.
Kelly Osbourne
Reality TV star Kelly Osbourne always seemed to be trying so hard to fit in with the cool music crowd over at MTV, but she never quite nailed it. We know she was going for a specific look here, but the hat and shoes were frumpy and the skirt wasn't much better. As for the blazer …
Ashanti
OMG, this makes us sad. The armband, the straps, and the pockets are not flattering at all — and they wouldn't be on anyone. Plus, these neutrals somehow clash with each other. Who thought it was a good idea to glue those pockets onto a pair of perfectly good pants? It's like they had leftover fabric from the vest and decided not to waste it. If you look closely, you can see the pants already had much more flattering slit pockets.
Emma Watson
Emma Watson was practically still a baby when she appeared on TRL in 2004. She's adorable and we love her, but we're mad at whoever told her to wear this jacket. Why did anyone think she should walk around New York City looking like a toy soldier? Not good!
Ryan Reynolds
It's pretty hard to believe that Ryan Reynolds would have picked this outfit out for himself. All that light blue was overkill, even for the Canadian surfer boy thing he had going on back then, but those jeans were downright offensive. Why did anyone think those were a good idea?
Carmen Electra
If we're being honest, Carmen Electra made more questionable fashion choices in the '90s and '00s than we can even count. It was on-brand for her. This isn't the worst of them, but it's pretty bad. The boots were totally left field, and her clothes looked like they were shrunk in the wash.
Jackie Chan
Just seeing Jackie Chan makes us so nostalgic, but what the heck was he wearing in this photo? His jeans had a frayed hem just like the cuffs on that barely visible white jean jacket tied around his hips. The crazy part? If you look closely at the shirt's logo, it seems it's from his own fashion line — one we didn't even know he ever had.
Jay-Z & Beyoncé
Even once she was boo-ed up with Jay-Z and promoting music that they were making together, Beyoncé could not give up the matching outfits. This is kind of disastrous, too. The all-denim looks were totally cheesy, and Bey's dress looked bizarre instead of cool. And no, we didn't like it when Britney and Justin did it, either.
B2K
We can't even. From the baby blue velour tracksuits to the bare chests and bellies, we don't even know what's going on here. B2K was all about the sex appeal, and lots of girls loved them, but looking back this seems incredibly silly. At least the one guy realized it was ridiculous.
Christina Aguilera
Christina Aguilera has never been one to follow fashion rules, but … oof. We don't even know where to look with this outfit. The scarf looks like it came from the clearance rack at a mall store, and the gaucho-length cargo pants were so unflattering even on her tiny frame. It's the prime example of early oughties excess.
Lil' Kim
We would never have expected Lil' Kim to show up to TRL in a boring outfit, but this is just all kinds of wrong. She's from Brooklyn so her choice of a tourist T-shirt worn as a skimpy minidress is even more confounding. And why oh why was there a bandana tucked into her boot?
Britney Spears
Britney, we love you, but this shirt was just ugly. Like, really, really ugly. We don't get why the 2000s were obsessed with shrinking down clothes to odd proportions. Oh, and that Peter Pan collar was seriously the pits. We won't even mention the sleeves, mostly because we don't understand them.
Eve
Let's just hope this 2000s trend doesn't make a comeback. Everything Eve was wearing here was so mini and torn and frayed and overstyled. The entire decade needed a good fashion edit. The worst offender here, though, was definitely that hat. It's absolutely tragic. Lots of hat choices back then were just strange.
Jennifer Lopez
J.Lo is a style icon and even she couldn't escape the trashiness of 2000s fashion. We're not gonna lie: This ensemble gives us trailer park chic vibes, and it makes no sense since Jen has probably never stepped foot in a trailer park being that she's a New York City native. It's just all wrong!
Andre 3000
Remember what we said about the hats? Andre 3000 is well-known for his eccentric fashion choices, but this one was definitely a doozy. We don't know what's going on with the furry hat and whatever those straps are, and we have no idea why he's wearing it with his grandma's shawl.
Jessica Simpson
We love Jessica Simpson, but she looked kinds of crazy here. We want to talk about that blazer, though. As we mentioned previously, the blazers of this era were problematic. Like a lot of the trendy clothing of the 2000s, blazers were worn tight and short — and it didn't look good on anyone.
