There have been songs about everything, from aliens to dirt and everything in between, but there are specific topics that get more songs written about them than others. Among those is the American cowboy, a cattle herder and ranch task master that has become a significant staple of this country’s lore.
Naturally, there is a lot of interest in cowboys, especially in the country music genre. Out of the hundreds, which ones are the best songs about cowboys? Here are the top 21.
1. Mammas, Don’t Let Your Babies Grow Up to Be Cowboys – Waylon Jennings and Willie Nelson
The quintessential cowboy song, “Mammas, Don’t Let Your Babies Grow Up To Be Cowboys” was originally released by Ed Bruce in 1975, but the most notable version of the song came three years later when Waylon Jennings and Willie Nelson teamed up for their Grammy Award-winning version. This serves as a warning to all mothers, as cowboys are rugged and tend to wander off the grid, but for many, that’s the ideal lifestyle.
Next: The best songs about sons ever recorded (complete list)
2. Should’ve Been a Cowboy – Toby Keith
One of Toby Keith’s earlier hits, “Should’ve Been A Cowboy” shows all of us that we should’ve gotten away from the mundane everyday office life to roam the open land and enjoy life. However, there’s an additional meaning to this 1993 hit. Keith explains that a police officer tried to approach a cowgirl at a bar but was turned down. This prompted one of his friends to tell him that he “should’ve been a cowboy.”
Next: The best ’90s country songs playlist
3. Save a Horse (Ride a Cowboy) – Big & Rich
Perhaps no other country song has been synonymous with sporting events quite like “Save A Horse (Ride A Cowboy),” which has been featured in commercials for football, stock car racing, poker, and every other sport you can imagine. Big & Rich came out with this anthem in 2004, and despite not receiving a whole lot of success on the charts, it has become a stadium country music staple. It’s not the deepest song, but it sure is catchy.
Next: Our ultimate playlist of the greatest country songs of all time
4. Rhinestone Cowboy – Glen Campbell
Another one of those crossover hits that earned mainstream success, “Rhinestone Cowboy” was released originally in 1974 without much fanfare. However, Glen Campbell released the album of the same name a year later, and it reached number one on the Billboard Hot 100. Though not about the traditional western cowboy, this song does capture that wandering feeling, detailing a western singer searching for fame while roaming the streets.
5. Cowboy Casanova – Carrie Underwood
One of the poppier and newer entries on the list, “Cowboy Casanova” was also one of the biggest country hits upon its release in 2009. Coming off of her “American Idol” victory, Carrie Underwood established herself as a country music superstar due to hits like this one, and it was nominated for several awards. The song shows that any man can become more enticing when donning a cowboy hat.
Next: Greatest American Idol contestants of all time
6. The Last Cowboy Song – The Highwaymen
You don’t see many musical supergroups these days, but back in the 1980s, they were more frequent across all genres. In country music, the biggest supergroup of all time was The Highwaymen, which comprised Johnny Cash, Willie Nelson, Waylon Jennings, and Kris Kristofferson. Among their classic hits is “The Last Cowboy Song,” which symbolizes the end of the cowboy era in American history as a tribute to a bygone time.
Next: The top ’80s country songs playlist
7. Cowboy – Kid Rock
There are a lot of different genres that Kid Rock covered all at once during his heyday in the late 1990s, and “Cowboy” is a testament to that. The song combines country, rock, and rap, and is considered by many to be the first “country rap” song.
While it’s a product of its era, this song is certainly catchy and caught on with fans of all genres. It also touches on the Los Angeles lifestyle, which Kid Rock wasn’t familiar with at the time. “I had to call up a guy I knew to get some facts about L.A.,” he said.
8. Cowboy Take Me Away – The Chicks
Back when they were still known as the Dixie Chicks, “Cowboy Take Me Away” was released alongside “Goodbye Earl” in 1999 and became one of the trio’s most successful songs to date. Going platinum twice, this song is about the relationship between band member Emily Robison and her then-boyfriend, who was an old-style type cowboy who became the first man her sister approved of.
9. Whatcha Gonna Do With a Cowboy – Chris LeDoux
Going back to the friendship between Garth Brooks and Chris LeDoux, Brooks teamed up with Mark Sanders to write “Whatcha Gonna Do With A Cowboy” for LeDoux. The song was released in 1992 and became a big hit on the country charts both in the United States and Canada, detailing how cowboys can be tough to deal with at times, but the relationship is worth it in the end.
10. I Want To Be A Cowboy’s Sweetheart – Patsy Montana
Another one of those classic songs released in the 1930s, “I Want To Be A Cowboy’s Sweetheart” is the oldest entry on the list, with Patsy Montana coming up with this hit in 1934. Like many of her songs, this one features a lot of yodeling and it has been covered over the years by the likes of Jewel, The Chicks, and LeAnn Rimes, just to name a few.
11. Back in the Saddle Again – Gene Autry
You can’t talk about cowboy songs without mentioning the man whose nickname was the Singing Cowboy. Gene Autry was an American icon, and while known for a lot of things, singing was first and foremost. This includes “Back In The Saddle Again,” released in 1939. The song is one of the first things that comes to mind when thinking about cowboys, down to the “Whoopi-ty-aye-oh” that has become synonymous with western music.
12. El Paso – Marty Robbins
An absolute classic, “El Paso” by Marty Robbins just screams classic western cowboy culture, all the way down to the record cover. It reached number one on both the country and Billboard Hot 100 charts upon its release in 1959. There were plenty of Robbins’ songs to pick from, such as “Big Iron,” but “El Paso” remains the most timeless of his classic hits.
13. Good Ride Cowboy – Garth Brooks
Another mention of Chris LeDoux, the late singer was friends with country music legend Garth Brooks. After coming out of retirement following LeDoux’s death, Brooks released “Good Ride Cowboy” as part of his “The Lost Sessions” album in 2005. The song is a tribute to LeDoux, including lines like “When she starts to twist, be more like Chris.”
Brooks said of the song that he wanted it to be up-tempo as it would be a tribute to LeDoux. He noted that LeDoux was never a somber type of person, so doing a tribute song that was mournful wouldn’t be on brand for his late friend, and it turned out to be the right call.
14. We Are the Cowboys – Willie Nelson
One of the newer entries on the list, Willie Nelson (like Chris LeDoux) has had plenty of songs regarding cowboys. From his 2020 album “First Rose Of Spring,” he released “We Are The Cowboys,” which does a great job of summing up the lifestyle of the American cowboy. “…the true sons of freedom,” Nelson says in the song. “We are the men who will get the job done.”
Next: The greatest country music singers in history (our complete list)
15. This Cowboy’s Hat – Chris LeDoux
Few country singers are as qualified to write about cowboys as Chris LeDoux, who was a world-class rodeo champion prior to becoming a country music star. With that, he released many, many songs about cowboys, and among the best of them was “This Cowboy’s Hat.”
The song details cowboys sitting at a diner and being approached by a group of motorcyclists who are shown the difference between a real horse and a steel horse. Long story short, don’t second guess a cowboy.
16. Cowboy Man – Lyle Lovett
Lyle Lovett simply has that look where you’d expect him to be a cowboy in a past life. Instead, he went the way of becoming a performer, but still had a lot of cowboy at heart. With that, he released “Cowboy Man” in 1986 from his self-titled album. It ended up being his biggest hit, too, reaching the top 10 on the country charts.
Lovett has performed this song at the White House, as well. He said that performing songs like “Cowboy Man” is “sorta like recess at school. It’s the best time, it’s the point of the day when you just get to do what you want to do and be free.”
17. God Must Be a Cowboy – Dan Seals
The life of the cowboy has been very glamorized in Americana, and songs like “God Must Be A Cowboy” really lend to that notion. Texas native Dan Seals loved that lifestyle, releasing this hit in 1984 from his appropriately named “Rebel Heart” album. This song is all about beautiful wide open spaces for horses to roam, which is why God must have been a cowboy.
18. A Cowboy’s Work is Never Done – Sonny and Cher
Obviously, there are going to be a lot of country songs, but this 1972 song by the legendary couple Sonny and Cher falls more into the psychedelic realm thanks to the trippy guitar play. It became a top 10 hit for the duo and talks about how even if a cowboy thinks that he can retire and ride off into the sunset, he’s always called back into action.
19. Cowboys and Angels – Dustin Lynch
While a lot of the musicians on this list had been long established by the time their cowboy song was released, that wasn’t the case for Dustin Lynch. “Cowboys And Angels” was the first single from his debut album, and what a debut it was. It took some time for the public to appreciate this song about the relationship between a rugged, sturdy man and a sweet angelic woman. The song would even reach the mainstream top 40 when released in 2012.
20. A Cowboy’s Ways – Dolly Parton
Though not one of her most commercially successful songs, “A Cowboy’s Ways” is the top cowboy song from the legendary Dolly Parton. It wasn’t released as a single, and comes from her 1983 album “Burlap & Satin.” It details how stubborn a cowboy can be, and how he’s set in his ways no matter how much love he may receive. Because of this, Parton says “…she wished he’d been a poet, So he’d know all those fancy lines to say.”
Next: The absolute greatest female country music singers of all time
21. Where Have All the Cowboys Gone? – Paula Cole
If you’re old enough to remember listening to the radio back in 1997, you couldn’t escape “Where Have All The Cowboys Gone?” The catchy Paula Cole tune was nominated for several Grammy Awards and was originally written several years earlier after she graduated from college. Though she has yet to match the success of this single where she asks for her John Wayne and Marlboro Man, she’s still recording music to this day.
As the Head Editor and Writer at Music Grotto, Liam helps write and edit content produced from professional music/media journalists and other contributing writers. He works closely with journalists and other staff to format and publish music content for the Music Grotto website. Liam is also the founding member of Music Grotto and is passionate in disseminating editorial content to its readers.
Liam’s lifelong love for music makes his role at Music Grotto such a rewarding one. He loves researching, writing and editing music content for Music Grotto.