The 1999 Video Music Awards didn’t stand out because of its zomg! moments -- unless you count the dude who crashed the Backstreet Boys’ acceptance speech by rushing the stage and exclaiming “Wake Up at 3!” (Tellingly, he was aiming for a TV deal.). This wasn’t Kanye interrupting Taylor or Madonna slipping Britney the tongue or Fiona Apple ripping the music industry or Jon Bon Jovi and Richie Sambora inventing MTV Unplugged on the spot. But viewed through the retrospective 2019 lens, the 9.9.99 event was as singular as its date. The event represented peak MTV at the height of the Total Request Live era, and yet it also paid proper homage to its pop and rock roots. We’ll never see its likes again.
You want a memorable location? How about the world-famous Metropolitan Opera House in NYC’s uptown Lincoln Center, home of Julliard and the New York City Ballet. A show-stopping opening number? I give you Aerosmith, Kid Rock and Run-D.M.C. invading the aisles as professional opera singers transform “Bawitdaba” into something almost legible, only to then connect the dots across MTV generations by belting out “Walk This Way.” A host with the most? There’s Chris Rock, fresh off Time dubbing him the Funniest Man in America. Dressed in all-white, he starts off his blistering monologue by proclaiming, “I may be the first black man in history to be on stage at the Met without a mop.” On boy bands: “Why the hell would you want to be a Backstreet Boy? Who’s on the front street... Big Bird? Didn’t you see New Kids on the Block? Don’t you know how this is going to end?!”
And that’s just the material before the first commercial break!
In an illustration of true music democracy, there was something for everyone. In a blissful 4:43 span, two ascendant pop acts made their VMA debuts: A black-leather-clad Spears showed off her dancing prowess to her debut single, “Baby One More Time,” followed by NSYNC tearing into “Tearin’ Up My Heart.” Ricky Martin capitalized on his breakthrough summer by swiveling his hips to “Livin’ La Vida Loca.” Nine Inch Nails delivered a rare live performance. Will Smith brought out the grieving mothers of slain rappers Tupac Shakur and the Notorious B.I.G. for unexpected poignancy. Jay-Z and Eminem both confirmed their respective rising empires with hits medleys, while iconic rappers Snoop Dogg and Dr. Dre showed up to bless the latter as being next in line. TLC played to the nationwide crowd with their smash “No Scrubs,” followed by a quickie dance routine set to 2 Live Crew's “(Dance) Too Much Booty in the Pants.” Prince introduced them, of course.
This was a lineup so stacked that three of the most-played (and best-enduring) rock songs of that year -- Smash Mouth’s “All Star,” and Blink 182’s “What’s My Age Again" and “All the Small Things” -- were relegated to pre-show performances. Jennifer Lopez had to co-present with Mark McGrath. An incongruous mix of artists both iconic (Diana Ross, David Bowie, Ozzy Osbourne) and fresh-faced (Christina Aguilera and Charlotte Church) took the stage as well. (Oh, as did Lil’ Kim’s purple-pastied boob, which an incredulous Ross jiggled.)
Of course, a VMAs show does not truly exist on the pop culture map if the Music Video Queen is not on-hand in all her glory. Enter a series of stylish drag queens paying tribute to Madonna, before her Madgesty herself strutted out to present Video of the Year. But not before she introduced Sir Paul McCartney. This was such a seminal moment that I choose to forgive the Beatle for announcing the winner as “Laurence Hill.”
These A-listers weren’t just on-hand for obvious promotional purposes — they wanted a piece of the zeitgeist. I’ll take it one step further and say that even though the VMAs has always prided itself on being the ne’er do well of awards shows, the show was more culturally significant than the Oscars during this period. Here’s who took home Moon Men in 1999: Will Smith, Lauryn Hill, TLC, Jay-Z, Beastie Boys, Backstreet Boys. Here’s who took home Oscars that same year: Shakespeare in Love (read: Harvey Weinstein), Roberto Benigni, Gwyneth Paltrow, James Coburn.
And while many Gen Xers like to point to The Real World in 1991 as the end of MTV’s heyday, never forget that the network’s calling card at the end of the decade was still the clip-centered TRL. And for the most part, the fans’ favorite videos each day were glamorous and sequined-studded gold. To this day, I can tell you the precise moment when host Carson Daly cut off the oft-replayed “Baby One More Time.” (Answer: Spears in the high-school gym!). And while The Daly Show debuted in ‘98 and continued into the ‘00s, it seeped into our public consciousness in 1999. Eighteen years after the network’s debut, a popular and acclaimed music video could still make or break the right artist. That’s why being recognized for your work at the VMAs was considered a landmark achievement. Eminem couldn’t fake his shock at receiving Best New Artist, as evidenced by his endearingly awkward acceptance speech. After all, his accompanying single, “My Name Is,” only reached No. 36 on the Hot 100.
It’s not like we ushered in 2000 and Spears disappeared from the spotlight: Like a pure pop song, this was a slow fade. YouTube was created in 2005; iPhones were introduced in 2007; Jersey Shore two winters later. TRL was cancelled in 2008, its final episode airing on a Sunday. A few videos managed to break through all the noise, like “Cry Me a River” and “Single Ladies (Put a Ring on It).” Now all our favorite videos are accessible, and we don’t have to frantically contact MTV to see them. And I ask you, friends, where’s the fun in that? Nope, we’ll never be able to recapture that warm September night when we all celebrated pop music at its zenith and a network at its most influential. It was a heck of a party. Alas, parties weren’t meant to last.