Why the ’99 MTV VMAs Are the Best VMAs

With the 2014 MTV Video Music Awards just days away, we are looking back on some of our favorite moments and highlights from the past 30 years of the ceremony honoring the best of music video world. While there have been a number of ups and downs, no iteration of the VMAs surpasses the 1999 ceremony. It was — hands down, no argument — the best. The year itself was one of the best for music with the introduction of Jennifer Lopez’s singing career, the explosion of TRL, and the return of the Red Hot Chili Peppers.

With all of that in mind, the MTV had a lot to celebrate. Led by Chris Rock, the last ceremony of the ‘90s turned out to be the last great VMAs. It had everything from Diana Ross jiggling Lil Kim’s boob to Lauryn Hill winning Video of the Year.

On a list of the show’s greatest hosts, Chris Rock is near the top. His delivery was on point the entire time. No celebrity escaped his wrath of jokes. Though his best line — a bit harsh but great — came when he introduced Britney Spears and *N SYNC. “Are you ready for some real lip-synching,” Rock screeched ahead of their performance. SNAP!

Speaking of Spears and that band of boys — 1999 marked the debut of both acts. It was each of their first performances and we all know Spears has gone on to deliver some of the best VMA performances of all time.

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