Best Country Music Songs About Cowboys and the Western Lifestyle

by Charles Craighill

The cowboy western aesthetic has grasped hold of the American heart since the days of the wild frontier. After all, the western frontier epitomized the American dream in its original context.

The cowboy’s story also plays a large role in the country music world as one of its many sub-genres. While western and cowboy music typically gets lumped together with country music, it does have certain specifications.

For instance, typical southern country music as seen in most Nashville artists combines elements of bluegrass, folk, blues, and rock. It also has some tropes and stereotypes that most lyrics fit into. As the blues typically talk about sadness and heartbreak, Nashville country music lyrics follow the trends of stereotypical southern life.

Similarly, Western and cowboy music combines cultural features from Mexico and southwestern America. It also includes some from Native American culture.

Here, we will take a look at some of the best country music songs that address the western cowboy aesthetic. These are the best songs we could think of about cowboys and the western lifestyle. This list has no particular order and no set number but attempts to consider all of the greats.

Classic Western Songs

While there are plenty of country songs about cowboys and the western way of life, very few actually fall into the classic western category. Even fewer still are songs sung by true cowboy characters.

As far as country music goes, not very many artists can truly embody the spirit of the west. George Strait is one of those guys. His song “Amarillo by Morning” feels about as much like a classic western song as anything in the modern era of country. His deep falsetto and dedication to true honky tonk country feels reminiscent of the days of the wild frontier. “Amarillo by Moring” not only sounds like a true western, but it’s spanning tale of rodeo fits too.

Another duo of dudes who could fit in well in the wild west are Waylon Jennings and Willie Nelson. Their song “Mamas Don’t Let Your Babies Grow Up to be Cowboys” also has the perfect western vibe. With lyrics about the nature of the cowboy and the perfect tasteful twang of pedal steel guitar, the song feels like it could blast from an 1800’s saloon in New Mexico.

Both of those two appeared again in the supergroup The Highwaymen, which released another one of the classic western songs. “The Last Cowboy Song” looks back on the time of the Cowboy with nostalgia. The song still fits the western bill, however, at least in its sound.

While the song lyrically reminisces on the end of an era, the sound feels like the cowboy era. Jennings and Nelson along with Johnny Cash and Kris Kristofferson, are the four members of The Highwaymen. They might be the most cowboy-like characters in country music at the time, and maybe ever. With their outlaw attitude, the group came close to imitating the classic cowboy of the wild west.

Best Cowboys by Female Artists

Patsy Montana wrote another classic western that has been re-sung over and over by countless famous acts. “I Want to Be a Cowboy’s Sweetheart” has been recorded by artists such as Phish, The Chicks, and Suzy Bogguss since she wrote it back in 1935. The narrator hopes to become a cowboy’s sweetheart married to the western lifestyle. By the end of the song, her wish comes to fruition.

Speaking of Bogguss, “The Night Rider’s Lament” is another song that was actually written by a real life cowboy. Though it may sound like it came from the 1800s, the song was actually written much more recently by Michael Burton in 1975. This song plays on the classic trope of cowboys choosing the nomadic outlaw lifestyle rather than love. In the song, the cowboy laments on his choice, but not for too long.

The Chicks have probably one of the most sentimentally romantic cowboy song ever. “Cowboy Take Me Away” comes off of their album Fly. Despite the lyrics, his song doesn’t literally talk about a romantic relationship with a cowboy.

However, it romanticizes the life of a cowboy in the modern age. The lyrics talk about the desire to live the life of a cowboy. The metaphor of “Cowboy Take Me Away” turns the romanticized life of a cowboy into a kind of love story where the Cowboy character really just represents what the cowboy life stands for.

Cowboy Western Songs in the Modern Country Context

While not many country music songs can truly fit into the Classic Western category, there still are dozens and dozens of country songs about cowboys. Here are some of the top ones sung about Cowboys. All of these songs seem to fall under the broader country music umbrella rather than the western sub-genre.

Another song that was written in the Nashville country music scene but addresses the Cowboy narrative is “Should’ve Been a Cowboy” by Toby Keith. This song, similar to the Chicks’ “Cowboy Take Me Away,” “Should’ve Been a Cowboy” romanticizes the Cowboy life in the modern age. The common theme for these songs is nostalgia for the older, simpler times. This feeling of nostalgia encompasses almost all songs that address the topic.

Garth Brooks has been one of the largest country music artists in the genre for a quarter of a century. Both in his Brooks and Dunne group and in his solo career, he has written plenty songs about cowboys and western life. From “Good Ride Cowboy” to “Whatcha Gonna Do with a Cowboy,” Garth Brooks loves the western aesthetic.

Those two songs also play on the classic stereotypes of the Cowboy western. Brooks also wrote “Beaches of Cheyenne” and “Much Too Young (to be feeling this old)” on his own along with “Cowgirls Don’t Cry” with Brooks and Dunn and Reba McEntire. While his sound is distinctly Nashville, his content nails the country-western feel.