1. It all went down at the Metropolitan Opera House in New York City on 9-9-99.
Which, yes, was a weird place to hold the award show.
2. Chris Rock hosted the show and delivered the best VMA opening ever.
“Why the hell would you want to be a Backstreet Boy? Didn’t you see New Kids on the Block, don’t you know how this movie is going to end?!”
3. Tommy Lee came dressed like a flasher, while his then-wife, Pamela Anderson, came dressed in something a glamorous Las Vegas madame would wear to the Kentucky Derby.
4. Britney Spears made her very first appearance at the show and she was definitely excited to be there.
5. NYSNC was there too and they seem confused on why Joey Fatone came dressed like Ronald McDonald.
6. Will and Jada Smith both wore outfits made out of a lot of dead cows.
Unless Will is wearing wolf skin?
7. While Christina Aguilera wore a lot of faux cheetah.
8. Someone let Busta Rhymes walk out of his house looking like this:
Did he raid Janet Jackson’s wardrobe?
9. Moby looked like C-3PO going to prom.
10. While Renée Zellweger arrived looking like she lost a fight with a hair crimper.
11. Korn was there, ‘cause kids thought they were cool.
12. Limp Bizkit was there ‘cause in 1999 we all had a serious lapse in judgement.
I’m sure Heather Locklear (aka Amanda Woodward on Melrose Place forever) regrets taking that photo with them.
13. J.Lo and Puff Daddy were the hottest couple of the night.
14. Kid Rock performed “I Don’t Want to Miss a Thing” with Aerosmith. OK, just kidding he performed “Bawitdaba.”
15. TLC took home the Best Group Video for “No Scrubs,” while looking like badasses.
16. Backstreet Boys thanked God for their award for Viewer’s Choice.
And also, probably, secretly prayed that NSYNC remain the No. 2 boy band.
17. Regis Philbin was there ‘cause it was 1999 and Who Wants to Be a Millionaire was all the rage.
18. Britney Spears performed at the VMAs for the very first time…
19. …along with NYSNC…
…in an epic “Baby One More Time” / “Tearin’ Up My Heart” mash-up performance:
20. Lauryn Hill slayed because it was her year.
21. Jay-Z performed a “Jigga My N****”/”Can I Get A…”/”Hard Knock Life (Ghetto Anthem)” medley.
22. The Beastie Boys took home the award for Best Hip-Hop Video and took the moment to talk about the need for peace.
23. Ricky Martin shaked his bon-bon while performing “Livin’ la Vida Loca.”
24. Madonna received a spectacular introduction, that took a look back at her past.
25. But, the real reason she was there was to present Video of the Year with none other than Paul McCartney.
And it went to Lauryn Hill for “Doo Wop (That Thing).”
26. But, even with Paul and Madonna in attendance, there was only ONE true star of the night and it was Lil’ Kim…
…who brought The Little Mermaid realness to the VMAs.
27. Even Diana mother-f’ing Ross couldn’t resist and had to cop a feel. Which led to this memorable moment.