38 MTV VMA Flashback Photos That Will Make You Long for the Late '90s and Early 2000s

From Britney's snake to Lil' Kim's pastie, prepare for the 2015 VMAs with our look back at the iconic fashion

By Jenna Mullins Aug 25, 2015 10:00 PMTags

'Scuse us, 2015 MTV Video Music Awards, we're really happy for you because you have Miley Cyrus hosting and Taylor Swift debuting her music video for "Wildest Dreams" and we're gonna let you finish but uh…

The MTV VMAs from the late '90s and early 2000s were the best VMAs of all time. Of all time.

(See what we did there? We made a very dated VMA joke while talking about the VMAs. You're welcome).

Why were the Video Music Awards so good from 1998 to 2003? The proof is in the pudding. Well, the proof is in the photos, but we bet if there were some pudding around the proof would be in that, too:

1. Alyson Hannigan and Sarah Michelle Gellar (1998)

Ron Galella/WireImage

It's Buffy and Willow in some truly questionable late '90s fashion!

2. Britney Spears (1999)

Dave Hogan/Getty Images

Britney came onto the scene with this face and the world was never the same.

3. Mark Wahlberg and Jennifer Lopez (1998)

Jim Smeal/WireImage

Just a casual threesome date to the Video Music Awards: Mark, J.Lo and J.Lo's hat.

4. Avril Lavigne (2002)

Dave Hogan/Getty Images

Someone should have told her she would grow up to marry the lead singer of Nickelback.

5. 'N Sync (2001)

Kevin Kane/WireImage

Do you ever wonder why this music gets you high? Speaking of high, whoever designed this set must have been pretty stoned. So. Many. Bright. Colors.

6. Lenny Kravitz and Gwen Stefani (1998)

Jeff Kravitz/FilmMagic

Tough question: Who has the better eyebrow game in this picture?

7. Madonna (1998)

Kevin Mazur/WireImage

Is there a photo more representative of 1998 than this one of the Queen of Pop?

8. Destiny's Child (2000)

Kevin Mazur/WireImage

Give Destiny's Child coordinating outfits or give them death.

9. Christina Aguilera and Fred Durst (2000)

Kevin Kane/WireImage

Remember when this performance was a thing?

10. Brandy (1998)

Jeffrey Mayer/WireImage

That's what we like to call a mullet dress. It's a shame not many people rock them anymore at the VMAs. Miley: Lookin' at you this year, girl!

FLASHBACK: These are the 20 most 2000s-y photos in TRL history

11. Julia Stiles (2000)

Ron Galella, Ltd./WireImage

Julia has yet to save the last dance at the time of this photo, but she is saving that iridescent pink dress for us.

12. Britney Spears (2000)

Kevin Mazur/WireImage

An icon is born.

13. Lil Kim (1999)

Ron Galella/WireImage

This photo is pre-Diana Ross boob-bouncing.

14. Christina Aguilera (1999)

Kevin Mazur/WireImage

Xtina's first VMAs! And she wore the official fabric scheme of 1999: hot pink lace and leopard-print.

15. Pamela Anderson (1999)

Jeff Kravitz/FilmMagic

That's the biggest hat you could find, Pam? Laaame.

16. Marilyn Manson and Rose McGowan (1998)

Kevin Mazur/WireImage

Ma'am, did you know you look quite naked in that dress?

17. Jennifer Love Hewitt (1998)

Ron Galella, Ltd./WireImage

That's the hairstyle every single female wore to their high school homecoming dances in 1998.

18. Jessica Simpson and Ashlee Simpson (2001)

Ron Galella/WireImage

This was before Ashlee went all punk on us.

19. Justin Timberlake and Britney Spears (2000)


You know what we're going to say here, right? TURN. BACK. TIME.

20. Andy Dick (2001)

Jim Spellman/WireImage

Andy Dick: the wallflower. He really has to learn to come out of his shell.

21. Pink, Christina Aguilera and Lil' Kim (2001)

Jim Spellman/WireImage

Voulez vous coucher avec moi ce soir.

22. Backstreet Boys (1998)

Jim Smeal/WireImage

Three out of the five of them are wearing vests. That's three people too many.

23. Britney Spears and 'N Sync (1999)

Kevin Mazur Archive/WireImage

How adorable do these guys look during their VMA rehearsal? So young. So innocent. 

24. Christina Aguilera (2002)

Dave Hogan/Getty Images

This is when Christina got dirrty. That's "dirty" with two t's. Respect.

25. Hanson (1998)

Jeffrey Mayer/WireImage

PSA: Hanson still does music and we recommend you listen to this song. Also, Taylor Hanson only got hotter after this photo. 

26. Nicky Hilton and Paris Hilton (2002)


This is when the Hilton sisters were just labeled as "models and socialites."

27. Beyoncé Knowles (2003)

Getty Images

This isn't Destiny's Child's Beyoncé. This IS Beyoncé. There is a big difference.

28. Avril Lavigne and Kelly Osbourne (2003)

Getty Images

We should put this photo in a time capsule and send it to aliens so they can study 2003 accurately.

29. The Rock (2000)

Getty Images

Oh, Mr. The Rock! Look at that shiny vest!

30. Will Ferrell (2001)

Getty Images

The puka shell necklace has been plaguing us since the early aughts and it's time to eliminate them forever. #DownWithPuka

31. Britney Spears and Christina Aguilera (2000)

Kevin Kane/WireImage

Until this moment, we honestly thought there was only room for one hot blond pop singer on the VMA stage.

32. Destiny's Child (2001)

Getty Images

Can you ever have too many photos of DC in their matching ensembles? Nope, didn't think so.

33. Britney Spears and Jennifer Lopez (2001)

Getty Images

BRB, having this iconic photo framed.

34. Justin Timberlake (2002)


This is a hard photo for us to look at because it meant that not only was Justin no longer with Britney, but he was no longer with 'N Sync. It's just too painful to remember.

35. Britney Spears, Madonna and Christina Aguilera

Getty Images

The era of the human race should be split into two time periods: before the moment Madonna kissed Christina and Britney onstage and after.

36. Kelly Clarkson (2002)

Getty Images

We see those chunky streaks, girl!

37. Jessica Simpson and Dream (2001)

Getty Images

We would now like to lead a rendition of Dream's "He Loves U Not" to honor this former girl group. 

38. Britney Spears (2001)

Kevin Kane/WireImage

Bow down. Case closed.

(Originally published on Fri., Aug. 22, 2014 at 11:57 am PDT)