Top 20 Western Songs of the Last 20 Years

The editors at American Cowboy present their picks for the greatest songs from the last 20 years. From true cowboy tunes to contemporary country, these songs are sure to encourage a trip down memory lane.
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The editors at American Cowboy present their picks for the greatest songs from the last 20 years. From true cowboy tunes to contemporary country, these songs are sure to encourage a trip down memory lane.
photo by Art Streiber

“I Swear”

John Michael Montgomery

Kickin’ It Up

Warner/Reprise Cntry Adv (1994)

“Any Man of Mine”

Shania Twain

The Woman in Me

Mercury Nashville (1995)

"Blue Clear Sky”

George Strait

Blue Clear Sky

MCA Nashville (1996)

“It’s Your Love”

Tim McGraw, feat. Faith Hill

Everywhere

Curb Records (1997)

“Wide Open Spaces”

Dixie Chicks

Wide Open Spaces

SBME Special Mkts. (1998)

The song hit #1 on Billboard charts, the album was Album of the Year, and the band was named some version of best new group at the CMAs and the AMAs, among others. And that was only the beginning. Natalie Maines’ lead powerhouse voice is proof of what talent ought to be and I’ll never forget when I saw Martie Maguire on the fiddle and Emily Robison on the banjo live on their Fly tour—these women can jam, for real. Forget everything else you know about the Dixie Chicks—when it comes to musical prowess, they still reign supreme. —Gabriella

“Amazed”

Lonestar

Lonely Grill

SBME Special Mkts. (1999)

"I Hope You Dance”

Lee Ann Womack

I Hope You Dance

MCA Nashville (2000)

I dare you to listen to this song and not be inspired. “I Hope You Dance” is a litany—a beautiful, melodious litany at that—of good advice. Womack advises listeners to not take a single breath for granted, never settle for the path of least resistance, and give faith a fighting chance. The song is touching, powerfully sung, and has a great message. There’s a reason it shot to the top of the charts. —Lauren

“My List”

Toby Keith

Pull My Chain

Dreamworks Nashville (2001)

“Where Were You (When the World Stopped Turning)”

Alan Jackson

Drive

Arista (2002)

“Redneck Woman”

Gretchen Wilson

Here for the Party

Sony (2004)

“El Cerrito Place”

Charlie Robison

Good Times

Dualtone Music (2004)

“4th of July”

Shooter Jennings, feat. George Jones

Put the O Back in Country

Show Dog Universal Music (2005)

“What I Really Mean”

Robert Earl Keen

What I Really Mean

Koch Records (2005)

“God’s Gonna Cut You Down”

Johnny Cash

American V: A Hundred Highways

Lost Highway Records (2006)

Though the lyrics aren’t original—the song is a traditional folk song—the Man in Black’s version certainly is. In this rendition, Cash is at his dark and subversive best. He takes a hopeful, upbeat gospel song and flips it on its head, turning the tune into something raw and brooding, infused with Old Testament grimness. When you consider that the song was recorded near the end of Cash’s life, it takes on an even deeper, more powerful meaning—it’s a song of redemption and reflection. —Lauren

“Chicken Fried”

Zac Brown Band

The Foundation

Atlantic (2008)

“In Color”

Jamey Johnson

That Lonesome Song

Mercury Nashville Records (2008)

“In Color” won Song of the Year at the AMAs in 2009 and was nominated for a Grammy in the Best Country Song category. The real test, though, is how a song makes the listener feel. The imagery is strong, the production is thankfully minimal, Johnson’s voice couldn’t be more appropriate, and he nails the delivery. The chorus stays in your head long after you’ve heard it and if you listen to the lyrics and aren’t moved, you’ve got a heart of stone. —Bob

“Horse Doctor Come Quick”

Corb Lund

Losin’ Lately Gambler

New West Records (2009)

“You and Tequila”

Kenny Chesney, feat. Grace Potter

Hemingway’s Whiskey

Sony Nashville/BNA (2010)

There’s nothing better than when mainstream jumps the tracks. Prior to this album, Chesney was selling over a million tickets to his shows each summer. This hauntingly beautiful composition is a result of stepping back from the limelight and looking deep into the soul of music… where he found Grace Potter. Completely unfamiliar with each other’s works until this song, the duo crosses musical boundaries and delivers fresh-yet-timeless tunes to our thankful ears. —Gabriella

“The Weary Kind”

Ryan Bingham

Crazy Heart: Original Motion Picture Soundtrack

New West Records (2010)

Ryan Bingham became an in-the-know sensation after his appearance in and collaboration on the soundtrack for the movie, Crazy Heart. His song, “The Weary Kind,” garnered an Academy Award, a Golden Globe and a Critic’s choice award. Bingham’s raspy voice, tragic background and West Texas roots give him Outlaw Country credibility, but this song showed the world his writing and performing chops. —Bob

“A Heart Like Mine”

Dwight Yoakam

3 Pears

Warner Bros./Via Records (2012)