The 20 best country songs of the 2000s (2023)

During the Y2K era, country music was changing rapidly. As the genre continued making its way further into the mainstream, pop influences crept in evermore. Still, traditionalists like Alan Jackson and George Strait stayed on the charts, proving that the genre had room for artists of all kinds.

Looking for a blast from the past? Flip through the slideshow for a list of 20 essential country songs from the '00s, from Alan Jackson classics like "Remember When" to Kenny Chesney's eternally sunny "Summertime."

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"I Hope You Dance," Lee Ann Womack

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The title track of Lee Ann Womack's third full-length album, "I Hope You Dance" was a massive crossover success after its release in 2000. The song was a #1 country and adult contemporary hit and charted at #14 on the all-genre Billboard Hot 100 thanks to Womack's soaring vocals and the song's inspirational, uplifting lyrics.

2 of 20

"Concrete Angel," Martina McBride

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This heavy ballad tackles the tragedy of child abuse with truly devastating lyrics. Released in 2002, it peaked at #5 on the country charts and has since been certified Platinum in the United States, selling more than 1 million copies.

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"The Good Stuff," Kenny Chesney

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Kenny Chesney scored a #1 hit with this nostalgic ode to the simple, wonderful moments in life in 2002. Even though it takes place in a bar, this song isn't about the booze — it's about making memories with the one you love.

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"It's Five O'Clock Somewhere," Alan Jackson and Jimmy Buffett

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For the second volume of his "Greatest Hits" collection, Alan Jackson teamed up with Margaritaville mayor Jimmy Buffett for "It's Five O'Clock Somewhere," an anthem for anyone who needs to get away from the nine-to-five.

5 of 20

"Redneck Woman," Gretchen Wilson

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Gretchen Wilson's 2004 debut single was a manifesto of sorts, an anthem for any self-proclaimed "Redneck Woman" who boasted her own distinct brand of rural femininity. It earned Wilson a Grammy Award in 2005 and remains her most enduring single.

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"Boondocks," Little Big Town

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This small-town anthem from powerhouse act Little Big Town was an instant success after its release in 2005, earning the band their first top-ten country hit. It's unabashed in its celebration of living in the "Boondocks," reveling in everything from tasting fresh honeysuckle flowers to fishing in the nearby crawfish hole.

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"My Next Thirty Years," Tim McGraw

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This reflective track, originally written by fellow country star Phil Vassar, was a #1 hit for Tim McGraw in 2000. Even though the song's ostensibly about turning 30, McGraw was already 33 years old when the song was released, though its message of building a better future for oneself is applicable to folks of all ages.

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"Red High Heels," Kellie Pickler

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Before she was a talk show host, Kellie Pickler was the "American Idol" alum behind "Red High Heels." Released on Pickler's 2006 debut "Small Town Girl," this song that's all about moving on from an ex who didn't deserve you — in great shoes, to boot — was a hit on both the pop and country charts.

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"Travelin' Soldier," The Chicks

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Included on the sixth full-length album from The Chicks, then known as the Dixie Chicks, "Travelin' Soldier" was first written by Texas songwriter Bruce Robison. The Chicks' emotional, stripped-down version brings extra gravitas to this emotional song about the love between a young woman and a soldier drafted to fight in the Vietnam War. It was the band's final major chart success before the controversy surrounding frontwoman Natalie Maines's comments regarding the invasion of Iraq in 2003.

10 of 20

"I'm Gonna Miss Her," Brad Paisley

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Subtitled "The Fishin' Song," this cheeky 2002 Brad Paisley hit was co-written by the artist while he was still a student at Nashville's Belmont University. It later became Paisley's third number one hit, and enjoyed some crossover success on the Billboard Hot 100, peaking at #29.

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"Summertime," Kenny Chesney

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Even nearly two decades later, this 2006 Kenny Chesney classic is still a perfect summer tune, ideal for any road trip playlist thanks to its sunny melody and lyrics that are totally fitting for those long, warm days.

12 of 20

"Bless The Broken Road," Rascal Flatts

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First recorded by the Nitty Gritty Dirt Band, Rascal Flatts turned "Bless The Broken Road" into a #1 hit in 2005. The song about love that endures even the biggest challenges became an instant favorite at weddings and has since sold more than 3 million copies.

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"Before He Cheats," Carrie Underwood

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Appearing on Carrie Underwood's debut album, which followed her win on "American Idol," "Before He Cheats" is the definition of a country crossover juggernaut. After its release in 2006, the song spent more than a year on the Billboard Hot 100 chart, peaking at #8, and was for a time considered the best-selling country song in history. It also earned Underwood a Grammy Award for Best Female Country Vocal Performance and Best Country Song.

14 of 20

"Your Man," Josh Turner

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Thanks in large part to his distinctively deep baritone, Josh Turner's "Your Man" was an instant success. The song debuted at #1, earned Turner two Grammy nominations and solidified him as the genre's hottest new heartthrob.

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"Wave on Wave," Pat Green

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Texas country is often categorized as distinct from "Nashville country," but Texan Pat Green proved that his sound could have broad appeal with the release of "Wave on Wave" in 2003. The song was a crossover success, selling more than 450,000 copies, and earned Green a Grammy nod for Best Country Song.

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"Whiskey Lullaby," Alison Krauss feat. Brad Paisley

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In the lengthy catalog of sad country songs, "Whiskey Lullaby" is certainly among the saddest. This tragic tale of alcoholism, suıcide, and ill-fated love was a wildly popular hit, earning this iconic duo the Song of the Year Award at the 2005 Country Music Association Awards.

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"Girls Lie Too," Terri Clark

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Canadian Terri Clark topped the charts in the '90s and brought that success into the 21st century with "Girls Lie Too," a rebellious anthem that dispels stereotypes about women and what they want. It was a #1 hit for Clark in 2004 and remains a fan favorite.

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"Don't Think I Don't Think About It," Darius Rucker

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Formerly the frontman of '90s rock act Hootie and the Blowfish, Darius Rucker struck out for solo success in the world of country music starting in 2008 with the release of "Don't Think I Don't Think About It," the lead single from his solo debut. It was a historic success for Rucker, making him the first Black country artist to score a #1 hit since the 1980s.

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"Need You Now," Lady A

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The title track of this group's, formerly known as Lady Antebellum, sophomore album, "Need You Now" boasts beautiful harmonies and relatable lyrics about loneliness and love that propelled the song to become one of the most downloaded tracks in history.

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"Come A Little Closer," Dierks Bentley

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Back when Dierks Bentley still had a big mop of curly hair, he was making country fans swoon with hits like "Come A Little Closer," which appears on his 2005 album "Modern Day Drifter." A #1 country hit, the song also scored Bentley minor success on the Billboard Hot 100.

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