Were the 1999 MTV Video Music Awards the Greatest of All Time?


With the 32nd annual MTV Video Music Awards this Sunday, the music world and Taco Bell both seem to be abuzz with VMA fever. But as excited as we are about this year’s telecast, VMA season has us nostalgic for some of our favorite Video Music Awards memories. One particular telecast we keep coming back to is the 1999 installment. Hosted by Chris Rock from right here in New York’s Metropolitan Opera House, it was heavily promoted for months to air on 9/9/99, using the repetition of The Beatles’ iconic “Revolution 9” to fully embed the date in our heads. The night was a celebration of music at a time when the industry was at its zenith and MTV held its strongest influence. It was also one heck of a show.

But was it the greatest Video Music Awards of all time?

See also: In Defense of the 1998 MTV Video Music Awards


Well, in one night, we had…

Chris Rock’s Incredible Monologue That We Still Quote.
“He need another hit like a crackhead need another hit” is our go-to desperate one-hit-wonders description.

Kid Rock, Run-DMC and Aerosmith Bringing the Rock-Rap Fad Full Circle
It’s rare MTV looks back at videos from yesteryear, but to recreate one from 13 years prior is pretty incredible and came off undeniably cool.


Will Smith Bringing Out Tupac’s Mother Afeni Shakur and Biggie’s Mother Voletta Wallace
With their sons’ deaths still fresh in the public conscious, Shakur and Wallace came together in a touching expression of unity.

Diana Ross Feeling Up Lil Kim
A musical icon lifts Lil Kim up to another level.

Eminem’s First Awkward Acceptance Speech Ever
One of the rare moments a winner is legit shocked that they won, Em is put on the spot here and gets through the struggle in the most charming way possible.

See also: Your Guide to the 2013 MTV Video Music Awards

Britney Spears and *NSYNC Making Us Feel Funny
For as much attention as the glitter flesh-colored suit and the snake got years later, black leather classroom Britney is the Spears we fell in love with. Plus, this was a time when backup dancer hair was at an all time most absurd.

TLC Performing “No Scrubs” and Bringing “Too Much Booty in the Pants” to a Nationwide Platform
As great as it was to hear TLC back on the radio in 1999, it was just as thrilling to know the entire music world had been commanded to “Dance! Too much booty in the pants!”

Beastie Boys Speaking Out About Woodstock ’99
Pretty great that, even when accepting an award for an outrageously fun video like “Intergalactic” (that beat out Lauryn Hill’s “Doo Wop (That Thing),” which went on to win Video of the Year. Just sayin’) the Beasties could drop some conscientiousness on the entire music industry.

The Return of Nine Inch Nails
The Fragile was to be the first NIN album since The Downward Spiral, and as reclusive as Reznor had been, it’s great he came back with a bang!

The Drag Tribute to Madonna and Paul McCartney’s Puzzling “Lawrence Hill” Joke
Madonna had won more VMAs than anyone, and Paul McCartney (of Wings and The Beatles fame) is an absolute cornerstone and icon of popular music, so to have them both together to close out the show really emphasizes the gravity in the world of music and entertainment this event had.

So, taking all of this into account, was 1999 the single greatest MTV Video Music Awards of all time?

No, we still think that would be 1997. You could still make a strong case for ’99 though!

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