POPSUGAR Celebrity

16 Moments From the 1999 VMAs That Can Never Be Topped

Aug 29 2015 - 12:00pm

The VMAs are this weekend, and while I'm excited about the upcoming show, I've been reminiscing about my favorite VMAs of all time: 1999. Chris Rock [1] hosted, Smash Mouth and Blink-182 entertained during the preshow, Lauryn Hill was the queen of the moonmen, and Britney Spears [2] 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 [3], Carson Daly, Janeane Garofalo, Mark McGrath, Jennifer Lopez [4], Johnny Depp [5], and, of course, Paul McCartney. Before this weekend's festivities, let's take a minute to remember what may be the greatest VMAs 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 Bass did not look amused.

Lil' Kim wore her infamous purple pasty.

Lil' Kim really paved the path for Miley Cyrus [6].

Diana Ross jiggled her boob on stage later.

Look at Mary J. Blige. She can't even with this scene.

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.

Was he naked under there?

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.

Mic drop.

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