American history is full of cowboys and the cowboy was actually something present in nearly all countries at one time. For Americans, cowboys became heroes in the ’40s and ’50s and young boys played Cowboys and Indians pretending to be the hero with the gun and a trusty horse.
Cowboy popularity has also been a part of American Country Music. True life cowboys have been singing country for decades. You’ll notice a lot of George Strait and Garth Brooks. George has been a roping cowboy for some time as well as being Garth’s hero.
Here is a list of the best of those classic country cowboy songs…
25. What The Cowgirls Do – Vince Gill
Balladeer Vince Gill cranked up the steel guitars and the electric guitars for his rousing number What The Cowgirls Do. The song is upbeat, catchy, and a tribute to all the great cowgirls out there. For as long as their have cowboys there have been girls to keep them company. Even if the cowboys would leave for life on the range there were always new cowgirls waiting in the next town. But don’t feel too bad for those girls. They have done a little leaving of their own over the years as well. Getting down and having fun isn’t just a cowboy thing. It’s what the cowgirls do.
24. How ‘Bout Them Cowgirls – George Strait
George Strait may not be riding the range out west and herding cattle for a living but he sure enjoys his time on his ranch. He’s a damn good roper too. Since he first found success on the country charts back in the early ’80s George has been singing about rodeos, cowboys and the good life of living like a true American. For the song How ‘Bout Them Cowgirls George sang out his love for cowgirls. Some may be a little stubborn sometimes, but they sure are the best thing a cowboy could ever find. You can’t put cowgirls in cities. They need to be out in the wide open spaces and they’ll find love there with cowboys like George Jones.
23. The Beaches of Cheyenne – Garth Brooks
Garth Brooks said in an interview with CMT some years back that he always wanted to be George Strait. Garth began writings songs and singing the same kind of songs that old George was singing. That included cowboy songs. The Beaches of Cheyenne is a classic cowboy song about a rodeo cowboy that is a bull riding son of a gun. Cowboys live a dangerous life. There was always plenty of danger out in the wide open prairies of the American West. Even rodeo cowboys today go up against some difficult situations especially the bulls. The cowgirls that get left at home are there to feel the pain when they find out their loved ones have passed. Some cowboy stories don’t end well, but when a great cowboy story gets put together with a great melody and a great performer like Brooks there is nothing better.
22. Beer For My Horses – Toby Keith & Willie Nelson
Toby Keith brought back the cowboy in 2003 with the song Beer For My Horses. Toby included good buddy and country legend Willie Nelson on the track and it became a country classic. In the song there is a declaration that justice needs to be brought about in today’s world much like it was back in the old west, in the time of the cowboys. Hang those bad dudes high up in the street and put a few more in the ground. No more messing around with nonsense. When someone does something wrong put them in their place. The song turned into a great music video featuring the two country greats and Toby even wrote and starred in a spin off feature movie.
21. Wolves – Garth Brooks
Garth Brooks was always known to put his personal favorite song as the last track on each of his albums. For his biggest studio release No Fences Garth chose a song that never became a single. Wolves was never a hit on radio, but the song was popular with all of Garth’s fans. Garth turned the story of a rancher and cowboy into a story of life. The rancher thinks about the heifers that the wolves pull out from his herd from time to time. Later in the song he relates this to the hard luck some people face in life – in this instance losing a house. It’s amazing to look back at this song released in 1990 and realize that housing is still a big issue today. Garth was quite the artist and he sure knew how to pick great songs to record. He was perhaps one of the best at picking great cowboy songs even if he wasn’t a full blown cowboy himself. We’ll give him a pass on that one. He’s a cowboy country singer.
20. Ghost Riders In The Sky – Johnny Cash
Johnny Cash had a voice like no other. His deep gravely growl could tell a story that made everybody pay attention. He recorded Ghost Riders In The Sky and with the song Johnny captured the attention of every cowboy fan around. The song has a cool yet dark sound to it. The song has all the classic cowboy images and the beat even reminds you of a horses trot. Any song that sings about horses snorting fire and the devil makes for one of the greatest country songs of all time. A little bit of learning life’s lessons in the this song and there was nobody better to sing it than old Johnny Cash.
19. The Cowboy Rides Away – George Strait
You’ll notice quite a few songs on here from one of country’s greatest stars George Strait. The Cowboy Rides Away is a great cowboy song that George often uses to ride out of stadiums as the final goodbye to his loving fans. The song uses an iconic image from life and screen of a cowboy riding away after settling a score or saving a town. In the song George sings about a cowboy that loses the love of his life. As things get settled down and the two finally realize it’s all over he knows this is where the cowboy rides away. It’s kind of a sad song yet there is always hope on the horizon just as there always was when the cowboy rode away in the movies. Cowboys had a habit of heading off into the distance. It was always the end of one part of life and the beginning of a new adventure.
18. My Heroes Have Always Been Cowboys – Willie Nelson
Willie Nelson sang about cowboys in his slow kind of fashion when he put together the song My Heroes Have Always Been Cowboys. In the song Willie describes all the unique things that make him love the thought of being a cowboy. We all grow up idolizing someone. It can be a parent, a sibling, and aunt or uncle. Other times it can be a person we see on TV or in a movie. Even more it can be a real life person we’ve met or have grown to know. For those out there that have had the pleasure of meeting a cowboy and seeing them work the cattle or working the range there is nothing more impressive than seeing a cowboy or cowgirl ride their horse with an effortless appeal. Lots of people have had heroes. Many of those people have looked up to cowboys.
17. Wild Horses – Garth Brooks
It’s amazing that many years after it was released on the album No Fences that the Garth Brooks song Wild Horses was promoted as a single. For whatever reason the record company or Garth thought this song deserved a chance and I think fans were the real winners. It’s hard to believe that not every country fan had already heard the song since nearly 20 million people bought the album but people loved this song when they heard it on the radio for the first time. It’s a song about a rodeo cowboy that tells his girl that he’s giving it up. He’s done. He’s through. He’s coming home to be with her and be the family man. But in the end he can’t give it up. He loves it too much. He’s made the promises before and he just can’t let himself do it. Wild horses keep pulling him in.
16. Wildfire – Michael Martin Murphy
Michael Martin Murphy will forever be remembered as the great country singer that recorded everybody’s favorite song about a horse – Wildfire. The song has that haunted kind of feeling. It fits the story of the song well as the narrator sings about a horse called Wildfire and his lost woman. The song is so great that it’s still popular and kind of has a cult following many years after its release. Michael Martin Murphy is a true cowboy that performed great cowboy songs for his entire career. Michael Martin Murphy made a living doing what he loved most. His passion came through on all his songs and he made a living singing cowboy songs. He had to be included on this list.
15. Good Ride Cowboy – Garth Brooks
In 2005, country music and cowboy song fans lost a treasure. Chris LeDoux succumbed to cancer at a young age. He was a great cowboy and a great performer. It’s no secret that Garth Brooks credits his ability on stage to Chris. To pay tribute to Chris three songwriters wrote an upbeat song and it was the perfect song. No one else could sing the song besides the man himself Garth Brooks. Good Ride Cowboy because a huge hit on radio and everybody was looking up stories and facts about Chris. It was a great tribute to one of the modern day real life cowboys.
14. Don’t Call Him A Cowboy – Conway Twitty
Conway Twitty can sing any kind of song. He put out Don’t Call Him a Cowboy and everybody was tapping their feet along to the beat. Conway is a country legend. He has more number one hits than most country fans have birthdays. His cowboy song was directed to women as a warning that there are quite a few guys that like to dress up and play cowboy while there are still only the true few that actually live the life and can love a woman like a cowboy. New York City and such places normally don’t have too many cowboys if any so there is no reason to look there. Head out to those country taverns and honky tonks where they play Conway Twitty and you’ll probably find a few true blue ropers.
13. That Girl Is A Cowboy – Garth Brooks
It wasn’t Garth’s biggest hit, but it became another classic cowboy song for country’s biggest superstar in 2006. The song is about a girl that has the nerve to stand up and have somebody’s back. She has the attitude, the look, and the toughness of a cowboy. Sometimes the best cowboys are not cowboys at all. This song is unique in the fact that it points out the nature of being a cowboy isn’t unique to guys. Women have their place in the modern west as well and perhaps they’ve even carved out there own niche in the cowboy world. Some girls are cowboys and the world is better for it.
12. Cowboys Like Us – George Strait
In 2003 King George Strait released another great cowboy song. Cowboys Like Us became another favorite for the baby boomers that loved to believe they were pat cowboys. I think the song was about bike riders – kind of the modern day cowboys. Or maybe it was about truckers. Either way the cowboy way of life was captured again in the song. Hitting the open road. Look for adventure. Talk about life but still act tough in front of our buddies. The song was kind of a sentimental song for the older generation. It reminded them that there is still adventure in life and there are still a few good cowboys out there just like us.
11. The Cowboy In Me – Tim McGraw
Tim McGraw released what would become his cowboy song in 2001. The Cowboy In Me was a three part description of a man realizing he has cowboy in him even though me may not look the part or live the actual lifestyle. Acting like there is nothing to lose. Foolish pride. Short temper. Testing the limits. All of these things are mentioned in the song and they all seem to fit the nature of the cowboy we have all created. Over time cowboys have taken on a personality we all relate to the image. Tim McGraw’s song is a beautiful depiction of what a cowboy means to people today how some modern me are spitting images of the old cowboys…even if they don’t ride horses or rope cattle.
10. Much Too Young (To Feel This Damn Old) – Garth Brooks
Garth Brooks wasted no time mentioning his cowboy and country artist hero. In Brooks’ first single Much Too Young (To Feel This Damn Old) became Garth’s first hit on radio in 1989. It was Garth’s first single and his record label was ready to put a stop to the promotion of the song once it started showing signs of stalling in the 40s on the charts. Feeling the pressure, Garth and his management team did some hard work and spent their own money to work the song at radio and at shows. The song climbed into the top ten and the rest was history. The song was about the tough life of a rodeo cowboy. Getting worn down on life was something country fans could relate to though and the song is still played frequently on radio today.
9. Everything That Glitters (Is Not Gold) – Dan Seals
This song was kind of the wild card on the list. Most might not think of this song when they think cowboy songs, but it sure fits all the criteria. Dan Seals was an adult contemporary pop star in the ’70s before he was a country star in the ’80s. One of his biggest hits was Everything That Glitters (Is Not Gold). The song is about a guy and his daughter. They have to make due on their own because the woman in their lives has left for the life on the rodeo. The song is unique because it kind of turns things upside down on our usual thought of the cowboy life. It can be lonely for those left behind, but the pull of the adventure and life on the road is too much for those cowboys out there.
8. What’cha Gonna Do With A Cowboy – Chris Ledoux & Garth Brooks
By 1992, Garth Brooks was able to get his hero a major record deal. Chris LeDoux had been a rodeo cowboy and a successful rodeo singer with the cred to back up the lifestyle he sang about. Chris was known for rocking shows. He would fly all over the stage and leave everybody in the crowd worn out just from watching him. The song is about the cowboy lifestyle. It takes the upbeat approach to what women will do with the cowboys. It’s a great song with two great country artists. One a true cowboy and the other a country singing cowboy that took country music to new heights.
7. Amarillo By Morning – George Strait
It was a remade song but George Strait turned Amarillo By Morning into a top ten hit back in the early days of his career. This is really the song that showed everybody George’s love for the cowboy lifestyle including the rodeo. The song has the rolling groove to it that kind of follows the way it can be out on the road. Lots of downtime alone with your thoughts. This song is true cowboy all the way through. It’s a great country song and although it wasn’t one of George’s million number one hits it sure was a memorable song in his collection.
6. Cowboy Take Me Away – Dixie Chicks
There aren’t many women on this list, but the Dixie Chicks make it near the top for their cowboy song. The tune is actually about the girls out there that want to be swept away by their cowboy dream men. The song was written by sister Marty for her sister Emily. At the time Emily was married to country singer Charlie Robson. He was the cowboy that swept her off her feet. It seems to be many girls’ dreams to find their romantic cowboy. However, cowboys don’t always turn out to be the dreams they want. The leaving, the hard work, the roaming, the adventure. It’s part of the mystique.
5. El Paso – Marty Robbins
We go way back for this classic cowboy song. Marty Robbins was one of the greatest country singers of all time. He recorded a great cowboy song with El Paso. The song is the story of a gunfighter. He falls in love with a Mexican beauty. The cowboy life takes over and eventually he is taken down in a gunfight. It’s the classic hero tale kids grew up watching on TV and in movies. The song is still popular on classic country radio today. Story songs have long been part of country music and cowboy story songs seem to have a more special place in the hearts of fans. This one is truly a great country cowboy song.
4. Rodeo – Garth Brooks
For Rodeo Garth Brooks left everything rodeo image out on the table. The song is all about the mud, the crud, the guts and the blood. The song shows listeners how gritty and grungy the rodeo life is. There is of course a woman in the story that has to put up with the life of loving a cowboy while hoping he someday changes his ways. The song has a unique sound and it’s probably what made it a hit initially. Now the song remains popular because people can still see themselves in place of the cowboy riding the bulls at the rodeo.
3. I Can Still Make Cheyenne – George Strait
George Strait seems to sing the best rodeo and cowboy songs. I Can Still Make Cheyenne is a song about a rodeo cowboy. He’s out on the rode feeling run down and worn out. He calls to say he’s heading home. His woman tells him not to bother. She can’t take it anymore. He’s gone too much and the cowboy life is too much. In the end the cowboy doesn’t know what to do but he knows if he heads out right now he can still make Cheyenne and the next stop on the rodeo tour. It’s kind of a sad song but a little look into the life of a rodeo cowboy.
2. Mamas Don’t Let Your Babies Grow Up To Be Cowboys – Willie Nelson & Waylon Jennings
The title of the song says it all. Mamas Don’t Let Your Babies Grow Up To Be Cowboys was a plea from the great Willie and Waylon to all the women out there to not let their kids grow up to be wild, restless, and a little crazy. The song became a huge hit for the duo and it carried their stardom to new heights. Still today people look back fondly at this song. There is just something about cowboys that people both love and hate. The lifestyle of working hard and earning a living out in the wild open mixed with the restlessness and leaving has an allure to it that makes us all wish we could live like that. Mamas may forever try to keep their babies on the straight arrow, but guys and gals will forever keep trying to be cowboys in some fashion.
1. Should’ve Been A Cowboy – Toby Keith
Toby Keith had the biggest hit on the ’90s with Should’ve Been A Cowboy. The song debuted in ’93 so it was already at a disadvantage. The difference between this song and others was the fact that the cowboy theme and the sentiment of guys wanting to be their heroes really connected with the country audience. It’s hard to imagine that when guys look back on their lives they don’t dream about being a cowboy. The reason cowboys were so popular in the ’40s and ’50s was because there was a sense of adventure, freedom, and accomplishment about living out west and being a cowboy. Should’ve Been A Cowboy is the all time greatest cowboy song. It expresses the love for the cowboy life and the envy all of the little kids in us had when we saw our heroes on the big screen or out on the actual range living the life.