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10 Country Songs Turning 20 in 2020

Lee Ann Womack accepts the single of the year award at the Country Music Association Awards show on Wednesday, Oct. 4, 2000 at the Grand Ole Opry House in Nashville, Tenn. Womack won the award for the song "I Hope You Dance." (AP Photo/Charlie Neibergall)

Despite being defined now by such new Nashville stars as Taylor Swift, Carrie Underwood, Dierks Bentley, Luke Bryan, Eric Church, Miranda Lambert, Rascal Flatts and The Zac Brown Band, the first decade of the 21st century began with '90s artists reigning atop the charts.

For a trip down memory lane, check out Wide Open Country's top 10 hit singles from the year 2000.

Note that these songs reached peak chart positions in 2000. Some, like The Dixie Chicks' "Cowboy Take Me Away," appeared on albums in 1999 (in its case, Fly).

10. "Buy Me a Rose," Kenny Rogers featuring Alison Krauss and Billy Dean

This gorgeous love song made 61-year-old Kenny Rogers the oldest country artist with a No. 1 hit. It might seem like a less obvious 21st century playlist addition than the works of Johnny Cash, Dolly Parton, Willie Nelson, Reba McEntire or Randy Travis, but it's the decade's first great song by a legacy act.

9. "It Must Be Love," Alan Jackson

Alan Jackson's covers album Under the Influence featured this tribute to the Gentle Giant, Don Williams. Like Williams before him, Jackson took the Bob McDill composition to the top of the Billboard charts.

8. "What About Now," Lonestar

Before Sugarland, Lady Antebellum and Little Big Town, Lonestar reigned as the new century's most popular vocal group. This single's runaway success proved that 1999's "Amazed" wasn't a case of lightning striking once.

7. "The Best Day," George Strait

A decade after the sentimental father-son song "A Love Without End, Amen," King George told a similar tale with this string of positive, life-spanning dad and lad experiences.

6. "How Do You Like Me Now?!," Toby Keith

One of Toby Keith's most familiar and fun tunes struck gold in the year 2000. A pushed-around underdog gives a former crush her comeuppance by living his best life in this bravado-fueled revenge fantasy.

Read More: The 10 Best Toby Keith Songs, Ranked

5. "Best of Intentions," Travis Tritt

Travis Tritt transitioned from one of the next big things in the late '80s alongside Garth Brooks, Clint Black and others to the surefire hit-maker behind his sentimental tune. This one-sided, would-be love story proved country music traditionalist Tritt's relevance in an increasingly pop marketplace.

4. "My Next Thirty Years," Tim McGraw

Tim McGraw never stopped being a big deal, as a solo artist or alongside Faith Hill, because of artistically rewarding yet crossover friendly hits like this 2000 cut and such 21st century classics as 2004's "Live Like You Were Dying."

3. "Cowboy Take Me Away," The Dixie Chicks

The century's first great traditional country hit didn't come from an Americana outsider or a gritty singer-songwriter. Instead, that fiddle and banjo accompaniment alone make this song about the courtship of Charlie and Emily Robison (now Emily Strayer) sound timeless.

2. "I Hope You Dance," Lee Ann Womack

The CMA Song of the Year for 2000 stands the test of time as a sentimental favorite with a life of its own. For better or worse, its success may overshadow the rest of Womack's tremendous catalog. Its music video co-stars Womack's two daughters, including current Americana artist Aubrie Sellers.

1. "The Little Girl," John Michael Montgomery featuring Alison Krauss and Dan Tyminiski

John Michael Montgomery's best showing of his sensitive side now stands out as much as one of several huge moments in 2000 for Alison Krauss. That same year, she played a major role in the multi-Grammy award-winning O Brother, Where Art Thou? soundtrack.

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10 Country Songs Turning 20 in 2020