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Best Songs of the 2000′s

Alan Jackson
Rick Diamond, Getty Images

A great country song can inspire you, make you laugh or make you cry. It may even enliven you to do crazy things like jump out of an airplane, dance like no one is watching … or do a little damage to a cheater’s beloved truck. The past decade has seen all of the above, as the genre has flourished, opening its doors to a more eclectic sound while keeping its tradition of thought-provoking lyrics. The Boot counts down our best songs of the 2000s. These aren’t just the tunes we heard most on the radio or that won the most awards, these were the country music news makers.

10. ‘Before He Cheats,’ Carrie Underwood (2006)

The same ‘American Idol’ winner who let Jesus take the wheel showed her sassier side by taking a bat to a pair of taillights. This crossover hit has wandering eyes seeing straight with its clever tale of a jilted girlfriend who gets sweet revenge.

9. ‘Stay,’ Sugarland (2007)

Only Sugarland can make you root for the “other woman.” This CMA, ACM and Grammy winning song gets live audiences cheering when its lonely heroine who aches for a married man finally throws him to the curb in the last verse.

8. ‘Redneck Woman,’ Gretchen Wilson (2004)

Not since Willie Nelson and Johnny Cash has a country singer been nicknamed the title of one of their songs. Gretchen shot to superstardom with this unapologetic tune that embraces the eccentricities of being a “redneck,” from walking around barefoot to keeping Christmas lights up year round.


7. ‘Courtesy of the Red, White and Blue (The Angry American),’ Toby Keith (2002)

The events of September 11 combined with his and his late father’s unwaivering patriotism led Toby to pen this song, which he originally never planned to release but only performed it live during his many concerts entertaining American troops. Promising terrorists to “put a boot up your ass,” the song proved both motivational and controversial.

6. ‘Not Ready to Make Nice,’ Dixie Chicks (2006)

The talented trio swept the 2007 Grammy Awards, winning all five categories in which they were nominated, on the strength of this defiant, wildly personal song. Airing their frustrations over what was perhaps the biggest backlash in country music history, the Chicks refuse to apologize for denouncing President George W. Bush, even if it means losing fans and even fielding death threats.

5. ‘Bless the Broken Road,’ Rascal Flatts (2005)

This poignant ballad celebrates lost love that ultimately leads down the path to true love. The song stayed at No. 1 on the country charts for five straight weeks and will stay on wedding playlists for years to come.

4. ‘Whiskey Lullaby,’ Brad Paisley and Alison Krauss (2003)

This tear-jerking tune, co-written by country legends Jon Randall and ‘Whisperin” Bill Anderson, tells the devastating tale of a man who goes to war and comes back to find his wife with another man. Stricken with grief, he drinks himself to death. Stricken with guilt, she does the same.

3. ‘Live Like You Were Dying,’ Tim McGraw (2005)

Tim dedicated this inspiring song to his late father, baseball great Tug McGraw, who passed away a year before its release. With their message of living life to the fullest, the lyrics include several adventures that might be on one’s ‘bucket list,’ like skydiving and bull riding.

2. ‘I Hope You Dance,’ Lee Ann Womack (2000)

This uplifting, crossover smash is about way more than just cutting a rug — it’s about “taking chances,” giving “faith a fighting chance” and never losing “your sense of wonder.” In short, Lee Ann’s career-defining song defines what country music is all about.


1. ‘Where Were You When the World Stopped Turning,’ Alan Jackson (2001)

The event that devastated our decade inspired our No. 1 pick for the hit of the decade. The “singer of simple songs” wrote it just a few weeks after the September 11 terrorist attacks, voicing the fears of a grief-stricken nation and giving an anything-but-simple message of hope and love in a time of devastation.

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