50 Best Country Songs from the Last 20 Years

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50 Best Country Songs from the Last 20 Years

1 of 50

Jo Dee Messina – “Lesson in Leavin'” (1998)

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

2 of 50

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.

3 of 50

Dixie Chicks – “Cowboy Take Me Away”‘ (1999)

The only acceptable way to sappily daydream about cowboys.

4 of 50

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.

5 of 50

Lonestar – “Amazed” (1999)

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

6 of 50

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.

7 of 50

Tim McGraw – “Something Like That” (1999)

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

8 of 50

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.

9 of 50

Alison Krauss & Union Station – “‘The Lucky One” (2001)

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

10 of 50

Alan Jackson – “Drive (For Daddy Gene)” (2002)

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

11 of 50

Dixie Chicks – “Long Time Gone” (2002)

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

12 of 50

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.

13 of 50

Johnny Cash – “Hurt” (2002)

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

14 of 50

Keith Urban – “Somebody Like You” (2002)

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

15 of 50

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.

16 of 50

Julie Roberts – “Break Down Here” (2004)

Like “Jesus Take the Wheel,” only way better.

17 of 50

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.

18 of 50

Carrie Underwood – “Before He Cheats” (2005)

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

19 of 50

Dierks Bentley – “Come a Little Closer” (2005)

Country music can in fact be sultry.

20 of 50

Faith Hill – “Stealing Kisses” (2005)

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

21 of 50

Little Big Town – “Boondocks” (2005)

Only these four perfectly entwined harmonies can make the word “boondocks” sound pretty.

22 of 50

Dixie Chicks – “Not Ready to Make Nice” (2006)

The Dixie Chicks get the final damning word in on the Bush/Iraq War saga.

23 of 50

Sugarland – “Stay” (2006)

24 of 50

Miranda Lambert – “Gunpowder and Lead” (2007)

This one might make you an advocate for 2nd Amendment gun rights.

25 of 50

Billy Currington – “People Are Crazy” (2008)

Simple truths in a simple song—and people keep getting crazier.

26 of 50

Zac Brown Band – “Chicken Fried” (2008)

The first song about fried meat to rocket straight to universal anthem status.

27 of 50

Kenny Chesney ft. Grace Potter – “You and Tequila” (2010)

Tequila fucks everyone up.

28 of 50

Lady Antebellum – “American Honey” (2010)

If you’re not convinced, watch the movie American Honey.

29 of 50

Lady Antebellum – “Need You Now” (2010)

An ode to the glorified booty call that resonates with 99 percent of the adult population.

30 of 50

Taylor Swift – “Dear John” (2010)

It might be about John Mayer. It definitely proves that Taylor Swift knows how to stir the pot.

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