As Prince once said: "Tonight, we're going to party like it's 1999!"
As the threat of Y2K loomed in the near future, stars like Kate Moss, Mel B and more were wearing the finest clothes, doing the wildest things and savoring every last moment before the ball dropped on New Year's Eve.
In terms of entertainment, the Sixth Sense was one of the biggest blockbusters of the year, alongside The Matrix and Tarzan, which all continue to be favorites in the library of movie titles of all time. It also happened to be the year that Hillary Swank won Best Actress for her role in Boys Don't Cry.
Then, there was Britney Spears' all-time favorite hit "Baby, One More Time" and the iconic music video where she dressed as a schoolgirl.
Meanwhile, in the world of fashion, trends were being set and stars were musing over which runway looks they would wear in the 21st century. Minnie Driver, Sandra Bullock and more were fixtures on the fashion scene at all of fashion's biggest shows.
To see who else made their appearance at shows across the globe, check out the gallery below!
Crazy to think that it's been 20 years since these stars sat front row at shows like Versace and Marc Jacobs!