25 Best Songs About Cowboys of All Time

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Written By Will Fenton

Founder of MidderMusic. From numerous bands to stints working in music shops, read more about me on the 'Here's My Story' page!

The American cowboy is a national icon, and countless songs have been written about them.

From country songs to folk songs to rock songs, the cowboy has been a subject of music for many years.

If you’re a fan of the cowboys or if you’re just looking for some good country music, then this list is for you.

Here are 25 of the best songs about cowboys, ranging from classic country songs to modern hits.

1. “Where Have All The Cowboys Gone?” by Paula Cole

“Where Have All The Cowboys Gone?” could not be avoided if you are old enough to recall listening to the radio in 1997.

The popular Paula Cole song, which was written some years prior when she had her college degree, was nominated for multiple Grammy Awards.

2. “Cowboy Casanova” by Carrie Underwood

In her famous song “Cowboy Casanova,” Carrie Underwood cautions young women about a dishonest guy.

She used a popular approach to the live performance of this song about “a snake with blue eyes,” using instrumentation that was heavily influenced by rock and her strong voice at the forefront.

The cowboy song performance included backup dancers and choreography as part of the Storyteller tour show.

3. “Should’ve Been a Cowboy” by Toby Keith

This is one of the most-played songs about cowboys in the 1990s.

For this early single, Keith played the part of an aspiring cowboy.

The protagonist of the song admits that he “should have become a cowboy” in the song’s chorus while daydreaming about cattle drives and enticing women.

His first album’s lead hit was this song.

4. “A Cowboy’s Ways” by Dolly Parton

“A Cowboy’s Ways” is the best cowboy music by the great Dolly Parton.

The song, which is from her 1983 album “Burlap & Satin,” wasn’t released as a single.

It describes how a cowboy, no matter how much affection he receives, can be stubborn and set in his ways.

For this reason, Parton says, “she wished he’d been a poet, so he’d know all those lovely lines to say.”

5. “Cowboys and Angels” by Dustin Lynch

The first song from Dustin Lynch’s debut album, “Cowboys and Angels,” was released in 2012, and what a debut it was.

It took some time for the general audience to understand and appreciate this song about a rugged, hard-working guy and a beautiful, angelic woman.

6. “El Paso” by Marty Robbins

The lyrics of this cowboy country music “El Paso,” read more like a movie script than a song since they are so full of vivid imagery and have such a dramatic plot.

It was written while Marty Robbins and his family were on vacation while driving across the Southwest.

He created a story about a man who fell in love while traveling.

But when he finds his lover with another guy, he kills him with a gun before running away.

Learn the outcome of this crazy tale by listening.

7. “Cowboy Take Me Away” by The Chicks

For the iconic 1990s song “Cowboy Take Me Away,” The Chicks show a gentler side than usual.

This cowboy song from The Chicks’ album Fly, which debuted at number one on the Billboard charts in 1999, features classic harmonies, clean fiddle riffs, and a catchy chorus.

8. “A Cowboy’s Work is Never Done” by Sonny And Cher

There will undoubtedly be more country songs about cowboys, but this 1972 song by the renowned duo Sonny and Cher leans closer toward psychedelia due to the trippy guitar riffs.

This song, “A Cowboy’s Work is Never Done,” which was a top 10 hit for the duo, is about how a cowboy is never able to retire and ride off into the sunset; instead, he is always called back into action.

9. “God Must Be A Cowboy” by Dan Seals

Songs about horses and cowboys like “God Must Be A Cowboy” certainly contribute to the idea that the life of a cowboy has been overly idealized in Americana.

Texas native Dan Seals, whose 1984 hit album was appropriately titled “Rebel Heart,” loved the cowboy way of life.

God must have been a cowboy, because this song is all about beautiful, wide-open areas where horses can roam freely.

10. “Mammas Don’t Let Your Babies Grow Up to Be Cowboys” by Waylon Jennings & Willie Nelson

“Mammas Don’t Let Your Babies Grow Up to be Cowboys” is one of the many songs with “cowboy” in the title.

This song, which the Western Writers of America group named one of the Top 100 Western Songs of All Time, advises mothers about the hard and sometimes callous lifestyle cowboys lead.

On their joint album from the 1970s, Willie Nelson and Waylon Jennings covered this song, which was originally written by married songwriters Ed and Patsy Bruce.

11. “Rhinestone Cowboy” by Glen Campbell

This song must be included on any cowboy song list.

Glen Campbell recorded “Rhinestone Cowboy” during a period when his career had taken a turn for the worst, and it became a tremendous comeback hit.

He hadn’t had a number-one hit in a while, and he wasn’t receiving a lot of acting work.

He immediately began recording this song, which tells the tale of a struggling artist who is attempting to break through.

It became one of the most well-known pieces of cowboy country music ever created after topping several charts and receiving numerous nominations and awards.

12. “Cowboy Man” by Lyle Lovett

Lyle Lovett simply has an appearance that makes you believe he was a cowboy in his previous life.

Instead, he chose the path of a musician; however, he still had a great deal of cowboy in him.

In 1986, his self-titled album was followed by “Cowboy Man.”

It turned out to be his biggest hit as well, peaking at number 10 on the country charts.

13. “This Cowboy’s Hat” by Chris LeDoux

“This Cowboy’s Hat” by Chris LeDoux is one of the best cowboy songs with a cowboy in the lyrics.

Chris LeDoux, a world-class rodeo champion before breaking into the country music scene, is one of the few country singers who are as qualified to write about cowboys.

With that, he released a lot of songs about cowboys, with “This Cowboy’s Hat” being one of the greatest.

In the song, a group of bikers approaches some cowboys as they are eating at a diner and demonstrates the difference between a real horse and a steel horse to them.

14. “The Cowboy Rides Away” by George Strait

Although this single was released in the middle of the 1980s, George Strait utilized it as his closing song on all of his tours and even centered the name of his final 2013–2014 tour on it.

The story of a cowboy who ultimately gives up on a failing relationship and rides out into the sunset is told in this song, “The Cowboy Rides Away.”

15. “The Cowboy in Me” by Tim McGraw

Tim McGraw talks about the cowboy lifestyle in this powerful song, which was recently featured as an acoustic tune on the well-known American TV series Yellowstone.

The country singer pays tribute to cowgirls at the end and sings about pain, regret, and overcoming adversity.

16. “We Are The Cowboys” by Willie Nelson

Willie Nelson has written several songs about cowboys.

He released “We Are The Cowboys” off his 2020 album “First Rose Of Spring,” which does a terrific job of summarizing the way of life of the American cowboy.

Nelson sings in the song, “The true sons of freedom.” “We are the men who will get the job done.”

17. “Good Ride Cowboy” by Garth Brooks

In 2005, Brooks released “Good Ride Cowboy” as a part of his “The Lost Sessions” album after coming out of retirement in the wake of LeDoux’s passing.

With lyrics like “When she starts to twist, be more like Chris,” the song is a tribute to LeDoux.

18. “Save a Horse (Ride a Cowboy)” by Big & Rich

The country duo Big & Rich first gained popularity on television during football pregame programs with their cowboy country music, “Save A Horse (Ride A Cowboy),” before establishing themselves as a more serious country group with classics like “Lost In This Moment.”

It has been the duo’s most well-known hit throughout the past couple of decades. It is a cowboy song about crazy cowboys and their pursuit of women.

19. “Wanted Dead or Alive” by Bon Jovi

In their iconic song “Wanted Dead or Alive,” Bon Jovi relates the harsh life of a rock musician to that of a bandit cowboy.

Singer Jon Bon Jovi sings of his “steel horse” and “loaded six-string” as he paints pictures of the villages they pass through while on tour.

They stay for only a short time, just like cowboys.

After doing their work, they move on to the next town.

20. “Back In The Saddle Again” by Gene Autry

The man known as the Singing Cowboy must be mentioned when discussing cowboy-themed songs.

While Gene Autry was known to be one of the legendary cowboy music artists and an American icon for many reasons, his singing was his most well-known talent.

This includes the 1939 song “Back in the Saddle Again.”

The song is among the first to spring to mind when thinking about cowboys, even down to the “Whoopi-ty-aye-oh” that has come to be associated with western music.

21. “I Want To Be a Cowboy’s Sweetheart” by Patsy Montana

The oldest song on the list, “I Want To Be A Cowboy’s Sweetheart,” was written by Patsy Montana in 1934 and is another one of those great cowboy songs from the 1930s.

This song, like many of hers, has a lot of yodeling, and throughout the years, artists like Jewel, The Chicks, and LeAnn Rimes, to mention a few, have all covered it.

22. “Space Cowboy” by Kacey Musgraves

Country singer Kacey Musgraves reflects on a failing relationship with her partner, who has left her, in this moody song.

In the chorus, she says, “I ain’t gonna fence you in,” as she accepts his leaving.

Rumor has it that Musgraves’ previous marriage to fellow country musician Ruston Kelly was the inspiration for this song.

23. “I Wanna Be a Cowboy” by Boys Don’t Cry

With their mid-80s single, “I Wanna Be a Cowboy,” the British pop-rock group Boys Don’t Cry brought the attraction of the cowboy way of life over the water.

The band was inspired to write the song in just one hour after watching Clint Eastwood movies the night before a recording session.

Although it fared well on the charts in other nations, including the US, Australia, and New Zealand, it struggled to garner significant popularity locally.

24. “Whatcha Gonna Do With a Cowboy” by Chris LeDoux

Chris LeDoux is known to be one of the most renowned cowboy music artists. 

Regarding the relationship between Chris LeDoux and Garth Brooks, Mark Sanders and Brooks collaborated to compose “Whatcha Gonna Do With A Cowboy” for LeDoux.

The song, which was released in 1992 and quickly rose to the top of the country music charts in both the United States and Canada, describes how, despite cowboys’ often difficult behavior, relationships with them are ultimately valuable.

25. “Cowboy” by Kid Rock

In his prime in the late 1990s, Kid Rock covered a wide range of genres at once, and “Cowboy” is proof of that.

Many people believe this song to be the first example of “country rap,” which blends elements of country, rock, and rap.

Songs About Cowboys – Final Thoughts

In conclusion, these are the 25 best songs about cowboys. 

While the genre of country music is often associated with cowboys, these songs show that the theme of cowboys extends beyond country music. 

These songs come from a variety of genres, including rock, pop, and folk.

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