See What the MTV Video Music Awards Looked Like 20 Years Ago


With the 2019 MTV Video Music Awards fast approaching, it’s time to party like it’s 1999!

The 1999 VMAs have been a tough act to follow for any VMAs broadcast of the 21st century. After all, 1999 was the year that Britney Spears made her VMAs debut and performed a mashup with ‘NSync, the year that Ricky Martin was “Livin’ la Vida Loca,” and the year that Lil’ Kim wore that NSFW dress.

Plus, in one of the show’s most touching moments, Will Smith introduced Afeni Shakur and Voletta Wallace, the mothers of slain rappers Tupac and Biggie Smalls.

TLC MTV VMA 1999 MTV Video Music Awards Looked Like 20 Years Ago
TLC pose with a Moonman at the 1999 MTV Video Music Awards Erik Pendzich/Shutterstock

Watch the video above to check out other highlights and lowlights from the “9/9/99” show, including our award for the most uncomfortable moment of the night.

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