On a night mostly remembered for Carlos Santana's eight-trophy haul for his comeback album Supernatural, the Dixie Chicks and Shania Twain made history of their own at the 42nd annual Grammy Awards. The Feb. 23, 2000, event was the first Grammy Awards ceremony held at the then-brand-new Staples Center, the Los Angeles sight of Music's Biggest Night for 18 of the past 20 years.

The Dixie Chicks picked up two wins for their stellar album Fly, which won Best Country Album, and its song "Ready to Run," which earned them Best Country Performance By a Duo or Group With Vocal. Twain's big night included wins for Best Female Country Vocal Performance ("Man! I Feel Like a Woman") and Best Country Song ("Come on Over").

Additional wins by country artists honored living legends, with George Jones' "Choices" selected as Best Male Country Vocal Performance and June Carter Cash's Press On earning Best Traditional Folk Album honors.

Of course, looking back at the fashion choices and superstar interactions from the red carpet is just as fun all of these years later as double-checking the winners' list. For a taste of that, enjoy this photo gallery featuring not just the Dixie Chicks but also some of the Nashville stars of the early aughts and rockers since embraced by Music City.

The 2020 Grammy Awards will take place at the Staples Center in Los Angeles, Calif., on Jan. 26. The televised ceremony will begin at 8PM ET on CBS; the pre-telecast Premiere Ceremony will be available to stream online earlier in the evening.

The Boot will be staying up late covering the most buzzed-about country winners, fashion and moments at the 2020 Grammy Awards. Readers can watch along with us by checking back to TheBoot.com for the latest Grammys headlines, liking The Boot on Facebook and following The Boot on Twitter.

Grammy Awards Rewind: See Country Stars on Music's Biggest Night Through the Years

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