Top 20 Songs About Cowboys and Cowgirls

The American Cowboy is known all over the world as a symbol of America. The cowboy life might not have been quite as glamorous as the silver screen portrayed it, yet most of the men and women who lived their lives as cowboys or cowgirls wouldn't have traded it for any big city job available to them at the time. In no particular order, here are our picks for the Top 20 Cowboy & Cowgirl Songs.



Junk Gypsy Amie Sikes welcomes the trail riders to the Wanderer Inn, as seen on GAC's Junk Gypsies. (action)

From: Junk Gypsies

Photo by: Sarah Wilson / Getty Images ©2014, GAC/ Scripps Networks, LLC. All Rights Reserved.

Sarah Wilson / Getty Images, 2014, GAC/ Scripps Networks, LLC. All Rights Reserved.

"Amarillo By Morning" by George Strait

Although Chris LeDoux recorded this song first, most people remember George Strait's version, which begins with a beautiful intro played by fiddle great Buddy Spicher. Here's a clip of George singing "Amarillo By Morning" live. The song is about a cowboy's love for the sport of rodeo, no matter what happens to him and no matter what he loses, saddles and girlfriends included. George, as most of his fans know, sponsors his own Team Roping Classic in San Antonio each year. He is no slouch as a roper either!

"Good Ride Cowboy" by Garth Brooks

This song, written by Jerrod Niemann (performing it in the clip above), Richie Brown, Bryan Kennedy and Bob Doyle, became Garth Brooks‘ tribute to his friend Chris LeDoux after the rodeo champ and singer passed away in 2005. It chronicles Chris’ rise to fame in the rodeo world and as a singer, as well as his down-to-earth ways as a father and husband. Chris and Garth became friends after the Oklahoma singer named the rodeo cowboy in his first single, “Too Young to Feel This Damn Old.” They also recorded a duet in 1992, “What’cha Gonna Do With A Cowboy.”

"Night Rider's Lament" by Suzy Bogguss

Upon hearing this song, one would assume it was written in the heyday of the cowboy. A little research finds it was written by real-life cowboy Michael Burton, but in a much more recent setting, circa 1975. It describes how one cowboy chose career over true love and how he sometimes thinks about what might have been. Those thoughts don’t linger long, however, as he quickly remembers why he chose the life of a cowboy on the range. The tune has been recorded by everyone from Chris LeDoux to Garth Brooks and Nanci Griffith, but Suzy has one of the great versions of the tune. Here she is singing it with Jerry Jeff Walker.

"Should've Been A Cowboy" by Toby Keith

Despite the fact that he is as much at home on a horse as he is on a stage, Toby Keith laments in this song that he should have been a cowboy. The Oklahoma native thinks he should have learned to rope and ride in a cattle drive, because he thinks as a cowboy he could have stolen the young girls’ hearts like his heroes, Gene Autry and Roy Rogers. Who among us hasn’t thought how glamorous it would be to be a cowboy on a big ranch somewhere out west, or at the very least, in a movie?

"Someday Soon" by Ian Tyson

Written by Ian Tyson, “Someday Soon” has been recorded by Judy Collins, Suzy Bogguss and many others and has charted in pop, folk and country. This 2009 video features Ian singing it – and you can see Suzy’s version HERE.

"Mamas Don’t Let Your Babies Grow Up to Be Cowboys" by Willie Nelson and Waylon Jennings

This video shows Willie Nelson and Waylon Jennings singing the Ed Bruce-penned song live from Farm Aid in 1986. The song is a tongue-in-cheek admonition for mothers to beware if their sons wanted to be cowboys when they grew up, and lists all the pitfalls should that happen.

"Texas In 1880" by Foster & Lloyd

One of Foster & Lloyd’s best-known hits, this tune talks about the cowboy way of life, but Radney Foster says it is really a song about the freedom to dream, to do what you want to do. Nevertheless, the song’s video is a great tribute to the life of the rodeo cowboy.

"This Cowboy’s Hat" by Chris LeDoux

Written by Jakes Brooks, this song might show the sentiment of a cowboy better than any song out there. While the lyrics don’t depict any cowboy activities like riding, roping and branding, Chris declares the simple reasons why the motorcycle gang member won’t be able to take his old cowboy hat off his head. It also conveys the message that although we may all be from different cultures, there are similarities among us nevertheless.

"I Wanna Be A Cowboy’s Sweetheart" by Patsy Montana

One of the great western numbers sung by a female, this song became the first million-selling song by a woman after Patsy Montana recorded it in 1935. The singer hopes one day to be a cowboy’s sweetheart, and by the end of the song, her dream has come true. The tune has been recorded by a diverse group of singers, including Phish, the Dixie Chicks, Suzy Bogguss, Lynn Anderson and LeAnn Rimes. This video is a live performance of the song by Suzy Bogguss.

"Whatcha Gonna Do With A Cowboy" by Chris LeDoux and Garth Brooks

This fun-loving tune was a duet with friends Chris LeDoux and Garth Brooks. The two ask the question of the lovely lady: “Whatcha gonna do with a cowboy when he don’t saddle up and ride away?” There’s no ready answer, so the listener is left to make their own decision as to how the gal who was looking for a cowboy will handle her newfound boyfriend’s lifestyle.

"The Last Cowboy Song" by The Highwaymen

The Highwaymen – Willie Nelson, Johnny Cash, Kris Kristofferson and Waylon Jennings – are one of many who recorded this song from the pen of Ed Bruce. They sing of recollections of the cowboy era and how it seems another piece of America has been lost. The song concludes, however, that there are still cowboys out there, and there will always be men and women who dream of that way of life.

"The Beaches Of Cheyenne" by Garth Brooks

“The Beaches of Cheyenne,” written by Bryan Kennedy and Dan Roberts with Garth, tells the story of a rodeo cowboy and his wife who have a fight before he is killed in a ride at a rodeo. The thought that the fight was never reconciled drives her mad, and his wife takes drastic measures to relieve her sorrow. It’s a ghost story that finds the woman forever walking the beaches of Cheyenne.

"Cowboy Logic" by Michael Martin Murphey

Written by Don Cook and Chick Rains, this is one of the best songs out there that explains the cowboy philosophy. Michael Martin Murphey recorded it during the time he first began recording cowboy tunes. As the song says, “If it’s a job, do it, put your back into it.” Plus, there is the humorous take on how you can spot a real cowboy from where he sits in a pickup truck!

"Much Too Young (To Feel This Damn Old)" by Garth Brooks

This tune, written by Garth Brooks, was his first single and set a trend for him in future recordings, to always include a song or two about the American Cowboy. It was also the song where he mentioned one of his heroes, Chris LeDoux, and unknowingly re-energized the singer/songwriter’s career so that more people heard about him and his music. Garth had many more tunes that championed the cowboy or the American West, but folks will always remember this one because it introduced him to the fans.

"The Strawberry Roan" by Marty Robbins

There’s not a cowboy in the world that won’t take the challenge of trying to ride the one horse that everyone else working on the ranch can’t ride. This is the premise of this old western song, which has been sung by numerous cowboy singers through the years. Marty Robbins loved cowboy music and recorded several albums of western tunes. This song had special meaning to him, as he sang it for a local Phoenix radio station back in the late 1940’s when he thought he was better than the singer the station hired! He got the job, and he sang it throughout his career. He recorded it on his Gunfighter Ballads and Trail Songs album, which also featured the classics “Big Iron” and “El Paso.”

"Cowgirls Don’t Cry" by Brooks & Dunn (featuring Reba McEntire)

One of the newer songs to pay tribute to the women in cowboy culture, “Cowgirls Don’t Cry” features country music’s modern day cowgirl/superwoman, Reba McEntire.

"Bandy The Rodeo Clown" by Moe Bandy

Moe Bandy sings about an integral part of the rodeo circuit, the rodeo clown. Many a cowboy owes his life to the quick thinking and fast footwork of a rodeo clown, who has drawn a ferocious bull or a bucking bronc away from the rider and given him time to get out from under the hooves or away from the horns of said animal. Although this rodeo clown may have seen his best years, he still is thought well of by his peers who remember the times he was the ultimate professional.

"Coyotes" by Don Edwards

A look at today’s world from the eyes of an old cowboy, who has no use for “this new world of asphalt and steel.” Written by Bob McDill, the song is a very poignant story of what happens when the world as someone knows it and worked in it begins to disappear. Don Edwards was the perfect match for this tune, because not only is he a great singer, he is a historian of the American West.

"Cowboy Up" by Joni Harms

Oregon native Joni Harms says she can’t live without western music. With songs like this one, she’ll never have to! The singer tells the story of a young cowboy who gets thrown and how a wise old cowboy gives him some sage advice, “You better cowboy up ? get right back in the saddle, as soon as you hit the ground.” As the young cowboy becomes one of the best, he calls his girl, only to find she’s married his best friend. At that point he finds that the old cowboy’s advice is not just for bronc busting!

"Happy Trails" by Roy Rogers & Dale Evans

A universally known song written by Dale Evans and often sung as a duet, this tune has closed many cowboy music concerts for years. It became Roy & Dale’s theme song and the two of them signed off The Roy Rogers show with it.

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