Skip to Content

10 Best Songs About Cowboys  

10 Best Songs About Cowboys  

No type of song describes America better than songs about cowboys. Country music is littered with these types of songs – songs that tell the tales of the early years of the United States and songs that give us a glimpse into what life was once like. 

This post may have affiliate links, meaning we earn a small commission on purchases through the links (at no extra cost to you). This does not change our opinion but does help support the site. Thank you!

In fact, there are more cowboy songs out there than any one person can even properly enjoy. The songs below offer a broad range of styles and artists, making it easier for someone to experience the excellent story telling found in country music. 

These songs offer a sometimes realistic, sometimes embellished glimpse into what life was like in the 1700s and 1800s. Some of them modernize the idea of the cowboy and how it translates to modern life. They may even change your opinion on country music as a whole. 

“Don’t Fence Me In” – Roy Rogers

Starting off the list is this Roy Rogers timeless classic. The song was originally written by Cole Porter and Bob Fletcher, but Roy Rogers truly made it his own with this rendition. The song is a little silly by today’s standard, but it’s catchy and provides listeners with a good idea of what country music was all about in the 1940s and 1950s. 

Overall, the song is all about a cowboy who just wants to live a carefree life with just him and his pony. 

Fernweh Editions Fern & Petals Candle


“Mamas Don’t Let Your Babies Grow Up To Be Cowboys” – Waylon Jennings & Willie Nelson

Nearly everyone has heard this song. Even those who aren’t a fan of country music know Willie’s famous line in this song. The song talks about the modern idea of a cowboy rather than the one seen in western films. 

The song serves as a warning to mothers. Willie and Waylon explain that the life of a cowboy is one away from family and home, and they urge their moms to steer them away from that lifestyle.


“Beer For My Horses” – Toby Keith & Willie Nelson

Willie Nelson’s long, successful career spans decades. He has worked with every notable star in country music and is revered by everyone who has ever stepped foot in Nashville. Alongside Toby Keith, he made the cowboy cool again in 2003 with the release of “Beer For My Horses.” 


“The Cowboy Rides Away” – George Strait

George Strait’s discography is full of two things – cowboy songs and love songs. He made a successful career not just singing about these topics, but he was imprinting vivid pictures into people’s minds. In full George Strait fashion, this song is about a cowboy in love.

The song also serves as a metaphorical goodbye to his fans. It is often used to close his set at concerts as a way to say farewell to the fans that came out to see him. His final tour was even called “The Cowboy Rides Away Tour.”


“Bury Me Not On The Lone Prairie” – Johnny Cash

This song has a long history. It began as a sea shanty that was called “O Bury Me Not in the Deep Deep Sea.” 

Sometime in the early 1900s, the song was rewritten to fit the cowboy. The song, which is more of an interlude than a song, serves as a prayer for Cash. After the prayer concludes, Cash closes out the song with a short vocal exhibition. 


“Git Along Little Dogies” – Sons of the Pioneers

“Git Along Little Dogies,” which is another song with a lot of history, is likely just as old as the cowboys of the old west. Sons of the Pioneers have the most famous version of the song, but the song is believed to be as old as 1893. The first known reference to the cowboy version is found in Owen Wister’s journal. 

The song is also known as “Whoopie-Ti-Yi-Yo.”


“Streets of Laredo” – Jim Reeves

Originating from the English folk song “The Unfortunate Lad,” “Streets of Laredo” tells a story of a young cowboy during his final moments of life. Jim Reeves tells the story of what goes through the young man’s mind after being shot by another cowboy. 

The dying cowboy talks about the events of his life while expressing remorse over the wrong things he’s done during his life. 


“Back In The Saddle Again” – Gene Autry

Written by Ray Whitley and Gene Autry, “Back In The Saddle Again” skyrocketed Gene Autry to fame. It’s still Gene Autry’s most famous song nearly 100 years later. 

The short song simply tells the story of the joy experienced by a cowboy when he saddles up his horse again. 


“Cowboys Like Us” – George Strait

George Strait delivered another classic cowboy song in 2003 with the release of “Cowboys Like Us.” It’s debatable what the song is actually about. Some say it is about bikers; some say it’s about truckers. However, one thing is for certain. It made a lot of people really feel like they were cowboys when it released. 

Fernweh Editions Candles


“Should’ve Been A Cowboy” – Toby Keith

Love him or hate him, there’s no denying that Toby Keith has been singlehandedly keeping the cowboy alive during modern times. This song released in 1993, but it’s still one of Toby Keith’s most cherished songs. 

The song serves as a fantasy for Keith as he talks about the life of a cowboy and how he would envision himself as a cowboy in the old west.