Never has there been a more iconic symbol of classic Americana culture than the cowboy himself. Whether you grew up in the country or the city, you’ve likely come across this popular archetype throughout some aspect of the American cultural canon.
As a result, the love of cowboys and the old west are on display in various popular songs. And so, in this article, I’m going to provide you with my favorite songs about cowboys and the old west lifestyle (which includes cowgirls and horses), in hopes that you might find a brand new track to vibe out or dance to in your free time.
Cowboy Casanova by Carrie Underwood
Now, of course, you can’t expect to have an article like this without a few country songs about cowboys, right? In the case of this Carrie Underwood tune, it’s a bit of a misdirection—at least in terms of our immediate perception of this genre.
When we think about cowboys, we’re conditioned to think about smooth, swash buckling heroes. But that, to some degree, is a fallacy. And in the case of Cowboy Casanova, it’s a downright trap.
In this song, Underwood sings of being at risk to become the next victim of love at first sight. She sees a smooth, attractive man leaning up against the record machine at the bar. He’s cool. He’s suave. He’s a Casanova.
But he’s also a snake. He’s a man that’s not to be trusted. And if you don’t run far away from him, he’ll destroy your heart.
Old Town Road by Lil’ Nas X
When Old Town Road came out, I remember hearing two big criticisms about the song. The first was that this wasn’t “real country music”—so much so that the remix decided to bring on Billy Ray Cyrus for some genre credibility,
And that was met with just as many side eyes. Even Billy Ray Cyrus himself was surprised with the song’s popularity.
But the other criticism I heard was, “why is a black man trying to do country music—there weren’t any black cowboys anyway.”
Well, my friends, that’s just not true. There absolutely were African American cowboys. I think the bigger question is—why isn’t this a larger part of country music storytelling and American pop culture entertainment?
It’s impossible for you to have been conscious in 2019 and not been familiar with this jam by Lil’ Nas X. The song became so utterly popular, you figured Lil’ Nas X’s fall from grace would be swift and painful. But the artist’s career is chugging along just fine, following up Old Town Road with an album that featured the very popular “Industry Baby.”
As far as Old Town Road goes, it couldn’t be dripped in more “cowboy-ness” if it was the official anthem for the Dallas Cowboys. With lyrics like, “take my horse to the old town road/I’m gonna ride,” and with a refrain that constantly tells us, “You can’t tell me nothin’,” this Lil Nas X track maintains the smooth outlaw vibe you’d expect out of a memorable cowboy song, but infuses it with an infectious beat that features a marriage of hip-hop and country sensibilities.
Sweet Baby James by James Taylor
Initially written as a cross between a lullaby and a traditional cowboy song, James Taylor depicts with music and words the tale of a lone cattle rancher whose only company is his horse. The song combines the sometimes desolate yet wayfaring life of a cowboy with the hopes and dreams James has for both himself and his family.
Written in a waltz style, the lyrics almost create a blanket of comfort for anyone weary from long days of lonely work in the elements. Maybe you’re even reminiscing about the simple pleasures of life you’re missing while attempting to smooth out the edges of a rough environment with song.
While it’s widely known this song was written for James’ older brother hence the lyrics about Massachusetts (where the Taylor family is from), the song itself details a western world, familiar to a typical cowboy. This is reflected in the first stanza and chorus.
There is a young cowboy who lives on the range
His horse and his cattle are his only companions
He works in the saddle and he sleeps in the canyons
Waiting for summer, his pastures to change
Goodnight, you moonlight ladies
Rockabye, sweet baby James
Deep greens and blues are the colors I choose
Won’t you let me go down in my dreams?
And rockabye, sweet baby James
A Horse With No Name by America
Who better to write an epic tale of a journey through the desert than three Americans who met and formed a band in London? At its core, this song is truly about getting out of the rut of rainy cities and adventuring into a new world.
Comparable to men leaving behind their coastal cities to find fortune in the west, one could imagine the lyrics and music of this song almost as an homage to the freedom and trepidation the cowboy might’ve experienced as they rode on their horses from desert to sea.
By the second stanza, America is telling us about the unforgiving circumstances of the landscape but ultimately finding comfort in that ruggedness. The chorus itself is an echo of the outlaw version of the cowboy.
A stolen horse with no name, finding solace in being alone and away from those who might seek to prosecute you.
I’ve been through the desert on a horse with no name
It felt good to be out of the rain
In the desert you can’t remember your name
‘Cause there ain’t no one for to give you no pain
After two days in the desert sun
My skin began to turn red And after three days in the desert fun
I was looking at a river bed
Wanted Dead Or Alive by Bon Jovi
This is an 80’s glam metal power ballad to really personify the wicked lifestyle of the classic cowboy outlaw. Bon Jovi’s hit single is all about prolific Old West heroes being both feared and revered by society.
While its modern spin on the cowboy myth is undeniable, you can’t help but imagine a horse-riding fugitive galloping through ghost towns of yesterday. He counts the days not by time, but by the bottles he drinks,—he only thinks in solitude, and always travels onward.
Sometimes I sleep
Sometimes it’s not for day
The people I meet always go their separate ways
Sometimes you tell the day by the bottle that you drink
And times when you’re alone, well, all you do is think
The cover itself of the album borrows elements of western fashion and is directly paying homage to the lifestyle of the west.
So, do you want to go beyond herding cattle and sleeping in canyons? This song will take you through the rock star-like qualities of the outlaw cowboy who rides into the unsuspecting village, steals the fortune, and gets the girl.
Cowboy by Kid Rock
While this is definitely a popular song with “Cowboy” in the title, it’s also one of the more unusual songs about the cowboy lifestyle.
Why? Well, think about it. When we conceive of a good cowboy song, what do we think about? I know, for me, I think about leather boots, a hot sun in the desert, and riding a horse on the open range.
But on this track, Kid Rock has different plans. On Cowboy, he wants to head out west and live a more Hollywood lifestyle. He wants to hang out with women that have “fake breasts” and drink with celebrities. He wants to stay at the Four Seasons.
In short, for Kid Rock, being “straight out the trailer” and making it in Hollywood is the ultimate come up. It’s the pinnacle of being a cowboy. It’s one thing to tame the Old West in the traditional, tried and true fashion we’re all accustomed to seeing. But for Kid Rock, he’s thinking about things a bit differently.
Someday Soon by Judy Collins
While the cowboy has risen to celebrity within the American cultural canon, we can barely tell the tale without the addition of some damsel either rescued by a cowboy or fallen deeply in love with one.
Someday Soon, originally written by Ian Tyson, was brought to life in the late 1960’s by the famous folk singer, Judy Collins. The song depicts a young hopeless romantic ready to face any circumstance to be with a rodeo cowboy. The rodeo cowboy, while not the original kind of the Old West, still serves as an important historical and modern symbol of the cowboy aesthetic, skill, and lifestyle.
Lassoing and dragging in cattle or attempting to mount a raging bull would surly have anyone privy to the trade secrets of rodeo cowboys. In Someday Soon, the lyrics also paint a picture of a young man who might put rodeo above all else – even his love.
This leads to conflict with the young woman’s father who might’ve lived a similar lifestyle in his younger days. The lyrics are complemented by the familiar sounds of slide guitar classic country fills. \
My parents can not stand him ‘Cause he rides the rodeo
My father says that he will leave me crying
I would follow him right down
The toughest road I know
Someday soon, going with him someday soon
Flora (The Lily of the West) by Crooked Still
Did you know The Ozark Hills has a rich cowboy history and was just as much part of the Old West? Flora is more than a century-old Irish and British folk song that rose to popularity within the western traditions of the Ozarks in the ’50s and ’60s.
This tune follows the structure of the ever-present murder ballad of the folk genre where the lyrics often depict the setup and murder of the subject(s) in the song. The song is written from the perspective of Flora’s lover who catches her with another man and kills him over her unfaithfulness.
Similar to the cutthroat, and violent justice of the outlaw cowboys, this person doesn’t play by the rules and is willing to kill another man over his love. The lyrics ultimately conclude in execution for the murder.
You imagine this man riding into town and engaging in a draw in an act of wild west vengeance over his lover. The instrumentation of strings and banjo put you in the Americana mindset and helps you see an older, cruel world of wild west brutality.
Now down in yonder shady grove
The man who was to come
Conversing with my Flora there
It seemed so strange to me
And the answer that she gave to him
It sort of me oppressed
I was betrayed by Flora
The Lily of the West
The American Quartet no. 12, Finale (Vivace Ma Non Troppo) by Antonín Dvořák
Not all great songs about the American culture have lyrics or even steel-string guitars. The US’ rich cultural landscape drew in admirers from all four corners of the earth. Even famous Czech composer, Dvořák, dedicated a lot of his compositions and anthropological study of music to the roots of early American music.
In the finale of his string quartet, The American, he fills the space with sounds of the old frontier of Iowa as it was in the late 19th century. Dvořák himself never wanted to be a symbol of old European music but a pioneer in composition that explored and fused abundant aural traditions of American music.
It’s similar to the pioneering spirit of the cowboy but beyond that – just the thematic material of the quartet instantly transfers your mind to what the unsettled frontiers might’ve been like. His triumphant and whimsical motifs might be reminiscent of herding cattle while musical moments of suspense remind you of the unforgiving and dangerous interactions faced within the Old West.
Folk Bloodbath by Noam Pikelny
Society loves tempestuous stories about good versus evil. And the first line of this song is “Louis Collins took a trip out west.” This sets up the the wild and sad events that will soon unfold.
Originally written by Josh Ritter, famed banjo virtuoso, Noam Pikelny puts a rootsy spin on this indie-folk favorite. The song was written with an amalgamation of old American folk song characters like Delia and Stackalee and the plot of their murders.
You can easily draw the comparison of a rowdy outlaw life to the crimes and events that unfolded in this story. Noam Pikelny’s baritone vocal with the smooth twang of his plectrum guitar harbors strong emotions tied to the old American spirit of these classic folk tales.
Louis Collins took a trip out west
When he returned, little Delia had gone to rest
The angels laid her away
Ridin’ Down the Canyon by Gene Autry
You’re getting back down to the roots here with a song all about the nostalgic and comforting elements of cowboy living. We’re leaving behind draw duels and fugitives for the honest and hardworking rancher type in Gene Autry’s, Riding Down the Canyon.
He finds comfort in saddling up his horse and riding the trails to watch the sunset. We immediately imagine the fiery neon clouds where the falling orange sun pokes through to cast light upon hills dawned with cactus and roaming cattle.
The laid-back fiddle accompanies a tremolo country guitar as you imagine yourself relaxing with your horse in the peace of finishing a hard day’s work. Gene Autry really knew how to put it simply for us:
I’ll tell you folks it’s heaven to be ridin’ down the trail
When the evenin’ sun goes down
Hey Cowgirl by Mac DeMarco
Cowgirls existed and were essential to the notoriety and sometimes infamy of the classic American cowboy. While there are plenty of country songs that depict the brevity and life of these cowgirls, we’re looking to Mac DeMarco to paint a different picture of the cowgirl. This song comes from his album “Here Comes the Cowboy.”
We’re immediately hit with a catchy and simple guitar riff while Mac joins in on vocal to place us in the position of a cowgirl who might be torn between her life in the country and a love in a city.
His indie feature is all about imploring a beloved cowgirl to join some dull trope of modern living that truly pales in comparison to the wholesome lifestyle she typically experiences. Whether it’s farmland or starry nights, would she give it up to watch TV?
Will you stay on the farm
Or will you come on back with me?
Give up all of your starts
To watch some TV
Billy The Kid by Marty Robbins
Marty Robbins is arguably one of the most reputable artists in the country-western genre – a genre quite important to the cowboy image and legend. Of course, Billy the Kid was pretty reputable in the vein of western outlaws. Marty Robbins’ timeless country twang takes on Billy the Kid’s story in this folky waltz of cowboy crime.
Billy the Kid is written in a classic waltz style; a common time signature for songs alike in the genre. A list of songs about cowboys wouldn’t be complete without some acknowledgment of Billy the Kid. While a lot of songs about cowboy outlaws tend to romanticize the rough lifestyle of crime, Marty Robbins spins Billy the Kid as a what not to do lesson of the old west.
Singing lines of making name for yourself through violence only to end up dead yourself. A true cowboy of the time was faced with a choice to live an honest life or go astray as Robbins put it. While the mythos of the cowboy wouldn’t be where it was today without these outlaws, we wonder who and what could’ve been spared in some of the infamous wraths of these historical figures.
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