Skip Nav

Pictures And Videos Of 1999 VMAs Britney Spears NSYNC

Why 1999 Was the Best VMAs of All Time

The VMAs are this weekend, and while I'm excited about the upcoming show, I've been reminiscing about my favourite VMAs of all time: 1999. Chris Rock hosted, Smash Mouth and Blink-182 entertained during the pre-show, Lauryn Hill was the queen of the moonmen, and Britney Spears joined *NSYNC for a medley of ". . . Baby One More Time" and "Tearin' Up My Heart." Fatboy Slim spun to "Praise You," Jay Z performed three of his hits, and the Beastie Boys took home the first-ever hip-hop award. On top of that, presenters included Tom Green, David Bowie, Will Smith, Carson Daly, Janeane Garofalo, Mark McGrath, Jennifer Lopez, Johnny Depp, and of course, Paul McCartney. Before this weekend's festivities, let's take a minute to remember what may be the greatest VMA show of all time.

Britney Spears and *NSYNC performed together.

I could just stop this post right now and this would still make it the best VMAs ever.

TLC performed "No Scrubs," then won best group video for it.

And they sat in front of *NSYNC. Lance does not look amused.

Lil' Kim wore her infamous purple pasty.

Don't even pretend you don't remember this.

Diana Ross jiggled her boob on stage later.

I told you so.

Diddy and J Lo were still dating.

Back then, he was still Puff Daddy and she wasn't even Jenny From the Block yet.

Eminem and Dr. Dre hung out with Diana Ross.


Lauryn Hill won four moonmen that night.

Plus she nailed her performance.

Britney Spears made this face.


Backstreet Boys performed a medley.

Of "I Want It That Way" and "Larger Than Life."

They also scored the viewer's choice award.

It was a good night for the Backstreet Boys.

Paul McCartney and Madonna chilled backstage.

Later, he called Lauryn Hill "Lawrence Hill."

Tommy Lee and Pamela Anderson were together.

That hat. Those pants.

Christina Aguilera wore this fancy leopard outfit.

The boots really pulled everything together.

Eminem performed with Dr. Dre and Snoop Dogg.

Does this count as old-school now?

Then he won for "My Name Is."

And he posed like that for the cameras.

Finally, Prince was there.

Enough said.

Image Source: Getty
More from POPSUGAR
From Our Partners
Paulini The Masked Singer Australia Elimination Interview
Justin Timberlake and Lizzo Music Collaboration
'90s Revolve Clothes That Are So Rachel Green From Friends
Who Plays Marc on This Is Us?
What Is HBO Max's Grease TV Spinoff Rydell High About?
Who Is Carlin Sterritt The Bachelorette Australia 2019?
Who Has Broken Up on Love Island Australia 2019?
15 Scary Moments From Kids Movies
How Jesse's Story Ends in El Camino: A Breaking Bad Movie
The Marvelous Mrs. Maisel Season 3 Trailer
Helena Bonham Carter Seeing Psychic About Princess Margaret
Kate Middleton's Blue Dress Is an Homage to Princess Diana

From Our Partners

Latest Celebrity
All the Latest From Ryan Reynolds