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Every year on September 9, I do two things—wish one of my closest friends a happy bday (you know who you are—hi!), and then always remember that time in 1999 when the MTV Video Music Awards aired on 9/9/99. Considering 1999 was probably the best year for pop music (in my humble, teeny-bopperish opinion), that was most definitely the greatest year for the VMAs, too. 2013 was pretty cray also thanks to Miley Cyrus’s performance and all, but let’s take a look back at the 9/9/99 VMAs for today’s OK! Old School, shall we? This is gonna be good.

Watch: The *NSYNC VMAs Reunion We’ll Never Stop Talking About

Getty Images

Getty Images

The 1999 show was hosted by Chris Rock and held at the Metropolitan Opera House in NYC.  Chris cracked many memorable jokes throughout the night, but remember especially when he made fun of Jennifer Lopez‘s ass for a solid 40 seconds? Remember, kids, this was before the years of Kim Kardashian, so what Chris is saying here was totally relevant for the times.

This show was also the one where Diana Ross grabbed Lil Kim‘s boob, which was covered only by a purple pastie. Lil Kim made the nipple pastie cool way before Janet Jackson did, guys.

Madonna also had a major night on 9/9/99. MTV did a tribute to Madge, who at that time was the artist with the most amount of VMA nominations, where drag queens came out dressed as Madonna’s characters from her past music videos.Then? Paul McCartney joined Madonna on stage and both presented the Video of the Year, also known as the “last award of the century.” OMG, this moment was magical.

And speaking of Video of the Year, Lauryn Hill was to the 1999 VMAs as Macklemore was to the 2013 VMAs. She won 4 moonmen that night, including Video of the Year, for “Doo Wop (That Thing).” This song is everything and looking back, this video was pure genius.

Another moment you may or may not have remembered? The Backstreet Boys won the moonman for Viewer’s Choice in 1999, and also performed a medley of BSB songs that is almost as amazing as the *NSYNC VMAs medley of 2013. Also, AJ’s belly shirt. Please look at AJ’s belly shirt.

And of course, there was the Britney Spears/*NSYNC collaboration. There are just genuinely no words for this.

Other major winners of the night were Will Smith, TLC,  Beastie Boys, Ricky Martin, and Fatboy Slim (?!), plus, Jay-Z won Best Rap Video for this song. And that is all. I think we can all agree that 1999 was the most amazing year for music ever.

OK! Exclusive: TLC Reveals Plans for New Music at the 2013 VMAs

What was your favorite moment from the 9/9/99 VMAs? Do you remember any of these happening? Tweet us @OKMagazine.

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