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Jo Dee Messina – "Lesson in Leavin'" (1998)

You've probably wished ill upon an ex, but your revenge fantasies haven't been so catchy.

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Clint Black ft. Lisa Hartman Black – "When I Said I Do" (1999)

For when you're blanking on what to put in your wedding vows, but you and your partner can harmonize really well.

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Dixie Chicks – "Cowboy Take Me Away"' (1999)

The only acceptable way to sappily daydream about cowboys.

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Faith Hill – "The Way You Love Me" (1999)

She wants you to see how good you are at making out. Love makes Faith Hill coo-coo, and it's infectious.

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Lonestar – "Amazed" (1999)

Imagining anyone singing this to you is the world's greatest ego-boost.

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Martina McBride — 'I Love You' (1999)

A dose of bubbly optimism that serves as a pregame for all of the angry post-breakup country songs you'll eventually turn to.

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Tim McGraw – "Something Like That" (1999)

This one will leave you craving for barbecue and summer lovin'.

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Toby Keith – "How Do You Like Me Now?!" (1999)

Ninety-nine percent of Toby Keith's music is shit, but this is an objectively good, satisfying song.

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Alison Krauss & Union Station – "'The Lucky One" (2001)

It's not often that a country singer will throw such subtle shade.

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Alan Jackson – "Drive (For Daddy Gene)" (2002)

All country music about cars/boats/trucks should be allowed on the merit of this song alone.

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Dixie Chicks – "Long Time Gone" (2002)

A stomping fiddle tune filled with country music puns and podunk imagery.

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Dolly Parton – "Stairway to Heaven" (2002)

This stripped-down cover proves the lasting brilliance of Led Zeppelin's classic—and gives it even more soul.

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Johnny Cash – "Hurt" (2002)

The novelty of Johnny Cash covering Nine Inch Nails never gets old.

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Keith Urban – "Somebody Like You" (2002)

Keith Urban has written a million and one good singles, but this one is irresistibly good-hearted.

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Brad Paisley – "Mud on the Tires" (2003)

The prequel to Brad Paisley's rousing track "Ticks," in which a couple checks each other for ticks. Nature is great.

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Julie Roberts – "Break Down Here" (2004)

Like "Jesus Take the Wheel," only way better.

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Loretta Lynn ft. Jack White – "Portland, Oregon" (2004)

We can't think of two people we'd rather get wasted with in the Pacific Northwest.

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Carrie Underwood – "Before He Cheats" (2005)

No one else can possibly make a little light property damage sound so much fun.

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Dierks Bentley – "Come a Little Closer" (2005)

Country music can in fact be sultry.

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Faith Hill – "Stealing Kisses" (2005)

Faith Hill makes a terribly convincing PSA against marriage and the solitary existence of a housewife.

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