Getty Images

33 VMA Photos That’ll Make You Miss ‘TRL’ More Than Ever

Justin and Britney? Lil' Kim and Christina? Gang's all here!

The VMAs that coincided with the heyday of “Total Request Live” were arguably one of the greatest eras in Video Music Awards history.

Why? Because for most of us who were old enough to understand the basics of the Y2K scare as it was happening (something about computers resetting to 1900?) but still young enough to secretly fear that it was all scientific gibberish for “ROBOT ATTAAAAAAACK,” “TRL” played a pretty fundamental role in our collective coming of age.

Related: 53 Moments The VMAs Burned Into Your Brain Forever

Just think: Justin Timberlake was still a part of *NSYNC! Britney Spears was not a girl but not yet a woman! Nu Metal had not yet lost its grip on the pop-music mainstream! “TRL” was, in a word, everything.

And if watching MTV’s music countdown every day was like poring over your yearbook and adding weirdly obsessive, entirely speculative notes about everyone in the margins, then the “TRL”-era Video Music Awards were like prom — or at least the highly choreographed version of prom that “She’s All That” had taught me was totally normal.

I’m not saying that the 2014 MTV Video Music Awards will be better or worse than these “TRL”-era VMAs past, but there’s a certain kind of magic — a low-rise, frosted-tipped magic — that can never be captured again. With today being Throwback Thursday and all, why not wallow in nostalgia?

1.) As this photo of Lil’ Kim from the 1999 VMAs proves, it was the best of times.

lil kim Getty Images

2.) Hold the “worst of times.” How could it be, with Brandy and Monica in full “The Boy Is Mine” swing in 1998?

brandy, monica Getty Images

3.) I mean, here’s working actor Andy Dick in character as Christina Aguilera’s fictional cousin, Daphne, embracing award-winning Limp Bizkit frontman Fred Durst. Give in to the 2001-ness of this photo.

limp bizkit, Getty Images

4.) Ricky Martin was livin’ la vida loca at the 1999 VMAs.

ricky martin Getty Images

5.) While Ja Rule and Ashanti were “Down 4 U” whenever you needed ‘em in 2002.

ashanti, ja rule Getty Images

6.) And judging by this 2001 pic, I think Eve just told Gwen Stefani and Will Smith a really polarizing joke?

will smith, gwen stefani, eve Getty Images

7.) But most of all, Sisqó wanted one thing from the New Millennium, and one thing only: to see that thong, dammit.

sisqo Getty Images

8.) Speaking of which, enter Britney’s iconic “Oops!” performance from 2000.

britney spears Getty Images

9.) She and fellow pop princess Christina grew up right in front of us. Here they are at that same VMAs.

christina aguilera, britney spears Getty Images

10.) Dear entire fashion industry: RECYCLE XTINA’S “DIRRTY” 2001 LOOK PLZ.

Christina Aguilera Getty Images

11.) Britney was still dating Justin in 2000. #poproyalty

britney spears, justin timberlake, *nsync Getty Images

12.) And Christina was still a card-carrying member of the 2001 “Lady Marmalade” matriarchy alongside Pink, Mýa, and Lil’ Kim.

pink, mya, lil kim, christina aguilera, Getty Images

13.) Outkast brought the fashion insanity to the 2001 VMAs.

outkast Getty Images

14.) While Macy Gray brought the promo. #BuyTheIdOniTunes

macy gray Getty Images

15.) Though our boy bands at the time didn’t do so bad themselves. Check out 98 Degrees in 2000!

nick lachey, 98 degrees Getty Images

16.) Not to mention *NSYNC that same year.

*nsync, justin timberlake Getty Images

17.) Or the year before at the 1999 VMAs. Etch this onto my tombstone tbh.

*nsync, justin timberlake Getty Images

Related: 21 Photos That Prove The 1994 VMAs Were The Nineties-est Thing Ever

18.) The Backstreet Boys circa 1998 saw *NSYNC’s turtlenecks, fur collars, and flame bedazzling, and raised them sensually flowing, unbuttoned button-ups and middle parts for days.

backstreet boys Getty Images

19.) But, we can’t talk about coordinated Y2K styling without mentioning Destiny’s Child. Those Tina Knowles originals from 2000 and 2001!

Destiny's Child Getty Images

20.) Honorable mention goes out to Korn in ’99. (Hayyyy, Fieldy.)

korn Getty Images

21.) While we’re on the subject of Beyoncé, who saw her marriage to Jay Z coming? One day they’re performing together in 2003, and the next — BAM! — they’re On The Run with bb Blue Ivy in tow.

beyonce, jay z Getty Images

22.) Oh, and speaking of ***flawless couples, remember when 50 Cent arrived on the 2003 VMA red carpet with Vivica A. Fox on his arm? Hmmm, maybe it was the other way around…

50 cent, vivica a. fox Getty Images

23.) How about OH MY GOD J.LO AND PUFFY!!!! The 2000 VMAs forever.

p. diddy, jennifer lopez, puff daddy Getty Images

24.) And then there was this legendary Madonna-on-Britney-on-Christina Aguilera makeout (featuring Missy Elliott) at the 2003 VMAs.

britney spears, madonna, christina aguielra Getty Images

25.) Mary J. Blige and Shakira made a cute ’02 pair of audience cuddle buddies, too.

mary j. blige, shakira Getty Images

26.) Same with Fred Durst and once-and-forever “TRL” host Carson Daly at the 2001 press podium.

limp bizkit Getty Images

27.) The “TRL”-era VMAs weren’t all love and hugs from Carson Daly, though. There was also plenty of ’00 brattitude courtesy of Papa Roach — P. Roach if ya nasty.

papa roach Getty Images

28.) This picture of Avril Lavigne flipping off the 2003 VMA cameras with Kelly Osbourne wearing a tee that reads “YOUNG WILLING AND EAGER” is tied with this for my favorite photo of all time.

kelly osbourne, avril lavigne, Getty Images

29.) “Did someone say brattitude?” – blink-182 at the 2000 VMAs but also all the time always ever.

blink-182 Getty Images

30.) Oops, almost forgot about Dre (and Eminem) at the 1999 show.

eminem, dr. dre Getty Images

31.) But, there was also a lot of love. After pop/R&B singer Aaliyah (seen here in 2000) died in a tragic plane crash at the age of 22…

aaliyah Getty Images

32.) …Her peers like Usher and Missy Elliott memorialized her at the 2001 VMAs.

missy elliott, usher, aaliyah Getty Images

33.) Yep, the “TRL”-era VMAs were truly a magical time to be alive. (Hayyyy, Dream and Jessica Simpson.)

jessica simpson, *NSYNC, Dream Getty Images


britney spears britneyspearsgifs/Tumblr

The 2014 MTV Video Music Awards are a wrap! Stick with us for the most talked-about moments, red carpet photos, the VMA winners list and more.

More From the 2014 VMAs
Bad at filling out bios seeks same.