24 of the most iconic videos from MTV’s 'TRL'

“...Baby One More Time” was initially written and pitched to a couple of well-known pop groups who turned it down. It then found a home on the debut album of an up-and-comer that’d soon find herself as the ultimate pop princess of the time, Britney Spears. As for the video, it struck the right chord with MTV’s audiences from the jump as it featured Spears bored out of her mind in class: relatable. From that point, everything from dance moves to fashion became a permanent fixture in pop culture.

It wasn’t like Outkast came out of nowhere with “Hey Ya!” They’d built themselves up as one of the most influential rap duos by then, but there was something a little extra special about the vibrancy of green and white ensembles adorning the throwback to American Bandstand. Plus, the song remains one of the catchiest earworms ever.

Green Day walked so Blink-182 could run naked through the streets in “What’s My Age Again?” It wasn’t their debut video, but it was the first to make them a permanent fixture on MTV and TRL.

NSYNC only released four albums but managed to become one of the most successful boy bands in history, and while a lot of their videos are considered some of the most memorable of TRL, “Thinking of You (I Drive Myself Crazy)” felt like the first time they weren’t just “that other boy band.” They were there to do their own thing, and they did it quite well in this video which featured the guys in silk pajamas in an asylum.

TRL wasn’t just for the pop artists of the time; a lot of rock bands graced the countdown with their presence, and one of the first was The Offspring. They had a few videos make the countdown, but none were ever as beloved as the silliness of “Pretty Fly (For a White Guy).”

Destiny’s Child picked up where the likes of En Vogue and SWV left off at the end of the 20th century with a level of poise that only worked in their favor because it took little to no time for them to become household names. They had a handful of videos make their way through the countdown, but there was something extra powerful about the camouflage outfits, the 2000s special effects, and the inspired song that made “Survivor” one of their most classic clips.

There was an abundance of blonde pop singers in 1999, but it’s safe to say Christina Aguilera was packing something vocally that was a bit unmatched in comparison. Her debut was inescapable, but 2002’s Stripped showcased a whole new side of her, and no one was upset about it. Especially after seeing the video for the lead single, “Dirrty.” It was far from where she started but a great place to be at that moment in her career because everything from the chaps she wore to how she pronounced “Dirrty” is still referenced today.

If there is one song from 2002 that everyone knew, it was “Dilemma” by Nelly featuring Kelly Rowland of Destiny’s Child. The song was undeniable, but the video may live on forever, thanks to the internet being obsessed with Rowland texting on an Excel sheet.

There was a heavy dose of pop towards the end of the ‘90s with Backstreet Boys and Britney Spears ruling every facet of life, but like with every generation, there was a heavy dose of teen angst in the air, and Nu metal music was there to aid anyone who was feeling it. In no time, Korn became the antithesis of the bubblegum pop and was quite the favorite on TRL, usually landing at No. 3. That spot was known as the “Korn spot” for quite some time, and it’s very much due to “Freak On a Leash.” Arguably their most visually stunning video, it was everything one loved about Hot Topic at the time and then some.

Eminem came out the gate with “My Name Is,” and so many of the videos that followed made a mark on TRL, but “Stan” was not only an enthralling video, it also birthed a term that is still commonly used today.

The video for “Crazy in Love” by Beyonce featuring Jay-Z was one of the simpler ones on the countdown, but it proved artists don’t have to break the bank to become iconic when they have that signature Beyonce catwalk strut.

Total Request Live is often looked at as a time capsule of the late ‘90s and the very start of the 2000s, but it lasted until 2008, which means it was able to dip its toes in the emo scene. With that, nothing made more of a splash than the cabaret meets mall punk ways of Panic! At The Disco. There are still so many who can’t be at a wedding, see a top hat, or close a door without thinking of “I Write Sins Not Tragedies.”

98 Degrees never had the same level of success as NSYNC or Backstreet Boys, but they did well enough for themselves in the late ‘90s and a bit into the 2000s with their romantic ways. This is why, out of all of their videos, the rom-com in music video form, “I Do (Cherish You),” stands above the rest.

Limp Bizkit first appeared on TRL with their cover of George Michael’s “Faith,” and it did well enough that when they started to release other videos — the votes remained. They had a healthy amount of their videos make the top 10, but after all these years, “Nookie” feels like their signature. It had Fred Durst’s signature red hat, the “Nookie” girls dancing, and gave way to an addition to millennial slang.

Cyndi Lauper feels like the ‘80s, Nirvana feels like the ‘90s, and Usher’s “Yeah!” featuring Lil Jon and Ludacris feels like quintessential music from the early 2000s with its boisterous declarations that made clubs during that time the only place to be. Well, that and living rooms because most people watching the video were in high school watching Total Request Live while doing their homework, but still. It gave the club fantasy from the comfort of home.

Long before there were conspiracy theories surrounding the actual identity of Avril Lavigne, she was simply everyone’s favorite necktie-wearing Canadian who took over TRL with every video she dropped. It was the story of a ballet dancer and a punk that captivated viewers like no other.

In many ways, Linkin Park bridged the gap between Nu metal and emo as their fusion of rap and rock balanced utter rage with emotional turmoil. It was the perfect combination at the time, and because of that, Linkin Park quickly rose to TRL icon status with videos like “One Step Closer” and “Crawling,” but if one were to ask former TRL watchers what video stood out the most for them, many would agree it was the surrealist video for “In the End” that was their best showing on the countdown.

An abundance of Afrofuturism excellence right amid the Y2K scare was nothing less than genius on TLC’s part when it came to “No Scrubs.” Everyone can recall their sexy silver space suits as they swung and danced around, delivering a sentiment no one has forgotten: “A scrub is a guy that thinks he's fly.”

Green Day had been around on MTV throughout the ‘90s, but they didn’t make any noise on TRL until their American Idiot era. The title track helped get them on the countdown, but it was the more somber tone of “Boulevard of Broken Dreams” that made them a TRL staple.

TRL wasn’t just for Britney and Christina; it lasted long enough for new pop stars to make their way to the top. Stars like Taylor Swift, who gave way to one of the most endearing hits of its time, “You Belong With Me.” Seriously though, how has that song not inspired its own teen movie? Could there be a Taylorverse one day? One can only hope.

Missy Elliott’s influence on the art of the music video goes far beyond the confines of Total Request Live, as her style was and is forever one of the most innovative. Especially when it came to the dance numbers and the tongue-twister lyricism. All of that said, that is why “Work It” made such a dent in the minds of TRL fans.

Mariah Carey had already set herself up as an icon years before Total Request Live was even a thought over at MTV with a cascade of No. 1 singles, and she added another to her lengthy list with 1999’s “Heartbreaker” featuring Jay-Z. The song was a phenomenal lead single off Rainbow, but it was the video that propelled it even further into the hearts of MTV diehards with two Mariahs battling it out over Jerry O'Connell.

Several artists who found themselves at the start of MTV in the ‘80s managed to find a whole new fanbase decades later on TRL, like Madonna, Michael Jackson, and even the Beastie Boys with their interstellar “Intergalactic.”

Backstreet Boys will forever be a fixture when conversations about TRL are had because they were on the show before it went live. Yup, not too long before the show was an afternoon delight, it was pre-recorded nightly with Carson Daly counting down only five videos (voted by no one). Backstreet Boys were on there quite often, so it’s not shocking that they'd be at the forefront when the show did turn into a phenomenon for the channel. And while they had plenty of videos come and go, it’s the airport-centric “I Want It That Way” that became their signature on the show and in their career.