The 50 Best Pop Country Songs of the Last 20 Years
From twangy karaoke classics to gut-wrenching ballads about whiskey.
Want to ostracize yourself from your peer group in one fell swoop? Fervently defend your undying love for Top 40 country music. That'll do the trick. Despite ire, skepticism, and stereotypes, the past 20 years have produced hundreds of good pop country songs. Here are the top 50, chosen purely for our own selfish reasons.
Jo Dee Messina – "Lesson in Leavin'" (1998)
You've probably wished ill upon an ex, but your revenge fantasies haven't been so catchy.
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.
Dixie Chicks – "Cowboy Take Me Away"' (1999)
The only acceptable way to sappily daydream about cowboys.
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.
Lonestar – "Amazed" (1999)
Imagining anyone singing this to you is the world's greatest ego-boost.
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.
Tim McGraw – "Something Like That" (1999)
This one will leave you craving for barbecue and summer lovin'.
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.
Alison Krauss & Union Station – "'The Lucky One" (2001)
It's not often that a country singer will throw such subtle shade.
Alan Jackson – "Drive (For Daddy Gene)" (2002)
All country music about cars/boats/trucks should be allowed on the merit of this song alone.
Dixie Chicks – "Long Time Gone" (2002)
A stomping fiddle tune filled with country music puns and podunk imagery.
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.
Johnny Cash – "Hurt" (2002)
The novelty of Johnny Cash covering Nine Inch Nails never gets old.
Keith Urban – "Somebody Like You" (2002)
Keith Urban has written a million and one good singles, but this one is irresistibly good-hearted.
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.
Julie Roberts – "Break Down Here" (2004)
Like "Jesus Take the Wheel," only way better.
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.
Carrie Underwood – "Before He Cheats" (2005)
No one else can possibly make a little light property damage sound so much fun.
Dierks Bentley – "Come a Little Closer" (2005)
Country music can in fact be sultry.
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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