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.
Another great performance went to Jay Z, who wasn’t supposed to have the extended showcase that he did. Although he was scheduled to perform, DMX didn’t show up to rehearsals or the show forcing Jay Z to fill the time. Fans were greeted with a stellar medley of “Jigga My N****,” “Can I Get a…,” and “Hard Knock Life (Ghetto Anthem).”
Of course, Ricky Martin wiggled his still-straight butt all over stage.
When it came to presenting awards, there were three standout moments. The first being when Wyclef Jean and Charlotte Church handed out the award for Best New Artist in a Video. Church performed an aria that managed to bring a stunned silence to Lincoln Center.
The other great moment came courtesy of Diana Ross, who strutted up to the podium and jiggle Lil Kim’s exposed breast.
On a more serious (and somber) note, Afeni Shakur and Voletta Wallace, mothers of the Tupac and the Notorious B.I.G., came together on stage to present Best Rap Video. It was a poignant moment to see the two women bring closure to the beef and drama surrounding the deaths of both rappers.
Ahead of handing out Video of the Year, Madonna was surprised with a gaggle of drag queens dressed as every one of the singer’s iconic looks of the past decade.
As for Video of the Year, that went to none other than Lauryn Hill for “Doo Wop (That Thing).” The singer was the big winner of the evening taking home four Moonmen.
The other night’s big winner: “Praise You” by Fatboy Slim. The video, directed by Spike Jonze, was a bizarre spectacular of performance art. In total, Jonze and Slim received three awards, including Best Direction in a Video.
While those two artists one big, there was at least one forgettable award: Best Artist Website. But we won’t dwell on that one too much. And since it’s the VMAs, there’s always regrettable fashion choices and 1999 was no different. And that’s part of why it was so great! Pamela Anderson in a big furry pink hat, Tommy Lee in a trenchcoat, and Renee Zellweger with crimped hair.
Dear 2014 VMAs, you have your work cut out for you.
[Photos: Getty Images]