10 Alluring Songs That Reference Cowboys | Playlist 🎧

1. Kesha, “Cowboy Blues”

High Road • Kemosabe • 2020

“Sing it with me, you shithead…” Yep, only Kesha would introduce a song in that manner, LOL. “Cowboy Blues” marks one of many ‘changes of pace’ that take place throughout High Road, the fourth studio album by Grammy-nominated pop artist, Kesha.  How so? Well, “Cowboy Blues” finds Sebert dipping into country and folk-pop.  Kesha wrote “Cowboy Blues” with Drew Pearson, Eric Leva, and Stephen Wrabel.

“I can’t help that I’m in bed with my three cats
I’m still obsessed with some boy
I shot whiskey with for one night
And I don’t remember if he remembers me
While I sit her thinking about him.”

Yep Kesha, that’s definitely the blues.  Prior to Rainbow, a country/folk-pop joint like “Cowboy Blues” might’ve been a shocking, about face.  But, after a thrilling cover of “Old Flames (Can’t Hold a Candle to You)”, among other unexpected numbers, we know anything is possible with her – she can’t merely be boxed in. Still, a four-minute ukulele-accompanied number wasn’t what I expected.  It’s successful though.  And, of course, ole girl still gets her bombs in:

“Did I fuck my whole life up?
Did I miss my one true love?
Was he right in front of me at the dive bar?
Was that you with thee cowboy blues?
You ask me, ‘Babe, take a chance, come on, just stay’
Why’d I leave you standing there at the dive bar?
I miss you with the cowboy blue suit.”

2. Chris Stapleton, “The Ballad of the Lonesome Cowboy”

Toy Story 4 (Original Motion Picture Soundtrack) • Disney Enterprises, Inc. / Pixar • 2019

“I was a lonesome cowboy / Lonesome as I could be / You came along, changed my life / And fixed what was broken in me…” Randy Newman is a terrific musician.  Wait – why are we talking about Randy Newman when “The Ballad of the Lonesome Cowboy” is attributed to Grammy-winning country artist Chris Stapleton? Well, Newman wrote the song, and the rest of the songs that appear on the original motion picture soundtrack for Toy Story 4, released in 2019.  Take one listen to brief “The Ballad of the Lonesome Cowboy,” and it’s clear that Newman’s distinct compositional touches are all over it.

“You can’t be happy when you’re all by yourself / Go on, tell me I’m wrong,” Chris Stapleton sings on the bridge, adding, “When someone takes you down from the self / And plays with you some, it’s wonderful.” Stapleton gives “The Ballad of the Lonesome Cowboy” an expressive vocal.  Like Randy Newman, Stapleton has his own distinct, nuanced vocals, which tend to make him stand out.  He sings this bluesy, country/folk superbly.  Sure, it’s a song intended for children that appears on a soundtrack (obvious by that ‘shelf’ lyric), but, it’s enjoyable aside from the soundtrack as well, thanks to great musicianship: writing, singing, and production.

3. Kacey Musgraves, “Space Cowboy”

Golden Hour • MCA Nashville • 2018

On “Space Cowboy”, one of many highlights from the Grammy-winning album, Golden Hour, Kacey Musgraves delivers beautiful, expressive vocals from the jump. The clarity that she sings is a major selling point.  Notably, she doesn’t employ twang, which takes away an ‘in your face’ countrified vibe.  While this is clearly a country song, it has a wider appeal than most because it doesn’t feel forced.

Musically, on “Space Cowboy,” the country cues happen naturally, particularly the subtlety and timely appearance of steel guitar. What does the title mean? Ultimately, Musgraves speaks about breaking things off, best evidenced by the chorus.

“You can have your space, cowboy
I ain’t gonna fence you in
Go on, ride, away in your Silverado
Guess I’ll see you ‘round again
I know my place, and it ain’t with you
Well, sunsets fade, and love does too
Yeah, we had our day in the sun
When a horse wants to run, there ain’t no sense in closing the gate
You can have your space, cowboy.”

4. Cash & Maverick, “Space Cowboy”

“Space Cowboy” • Cash & Maverick • 2019

There have been a number of notable “Space Cowboy” songs.  One of the more recent examples hails from Kacey Musgraves (“You can have your space, cowboy”).  That said, did you know that there’s another “Space Cowboy,” courtesy of pop brother duo and TikTok stars Cash & Maverick? Their countrified, hip-hop-infused pop joint continues a trend of songs incorporating country/cowboy culture – you can thank Lil Nas X’s “Old Town Road”, at least to a certain degree.

Where the Kacey Musgrave edition of “Space Cowboy” is more chill and mellow, “Space Cowboy” in the hands of Cash & Maverick has more of a youthful pulse.  Is it tongue in cheek? Totally, but given the hip-hop beat, and the energy of the two teens, it’s hard not to deny the infectious of this cowboy joint, particularly the chorus.

“I’ve got a brand-new horse
Pedal to the floor
Space cowboy like
Luke with the force
Feeling like I’m winning
This is the beginning
Grab the bull by the horns, yeah
This is how I’m living.”

5. Tyler, the Creator, “Cowboy”

Wolf • Odd Future • 2013

“I am the cowboy on my own trip / And I am the cowboy on my own trip / And I am the cowboy on my own trip / And I am the cowboy.”  Isn’t it self-explanatory?  If not, lemme spell it out for ya! Tyler, The Creator is the “cowboy on [his] own trip,” or so he asserts on the song, “Cowboy,” from his 2013 album, Wolf.  Essentially, the Grammy-winning rapper is telling the world that he holds his own destiny.

There’s plenty to like about “Cowboy.” From the production end of things, this record bangs.  When Tyler, The Creator is in the producer’s chair, good things happen.  Here, there’s an rhythmic groove, jazzy cues, and an overall spare approach to the backdrop.  This gives “Cowboy” a distinct, underground vibe.  From a lyrical perspective, there are a number of memorable lines, beginning with “Knock knock motherfucks, it’s me Mr. Clusterfuck…”

Other clever lyrics? What about “This is life, truthfully, I just want to fly some kites / Grab Salem and Slater and go around, riding bikes,” “…Going hard as riga mo [rigor mortis] …,” or “I’m never civil, fuck Lincoln.” That’s Tyler, the Creator in the nutshell. Despite his polarizing personality, and some offensive references and ideas, on “Cowboy,” he reflects on himself, fame, etc. Oh, and for fans of the rapper early on, his alt-persona as a therapist makes an appearance.

6. ALMA, “Cowboy”

“Cowboy” • Virgin • 2018

“I’m a cowboy, remember my name / Remember my name / And where I came from / Cowboy.” In pop music, a feisty attitude can go a long way; A song where the artist showcases an interesting personality bodes well. That’s exactly what happens to Finnish pop musician, ALMA, on “Cowboy”.  She turns up the personality and ‘that attitude’ big time, with some ‘colorful’ language to further amplify things.

Even though “Cowboy” is a pop record, it embraces a countrified, ‘western’ sound to capture the cowboy sensibility.  Furthermore, it’s a darker record, in a minor key.  Despite lacking that happy, optimistic feeling, it’s rhythmic and quite appealing to the ears. ALMA delivers a sensational vocal, filled with its fair share of raspy, gritty, and nuanced moments.  Among the best moments is the pre-chorus, which sets up the aforementioned chorus.

“I still got lovin’ for ya
But only some of you, yeah, yeah
Already said all of my last goodbyes
I think about you, mama
I think about you, daddy
While I start these fires.”

The second verse is half the length of the first, but still worthwhile, particularly the edgy opening: “Honest as a virgin, pissin’ holy water / Swear I’ve never felt so free” The intensity of the record picks up even following the contrasting bridge, thanks to placing profane emphasis on “cowboy” via mother-… fill in the ellipses. There’s plenty to like about “Cowboy,” led by ALMA’s terrific voice and big personality.

7. Yelawolf, “Ghetto Cowboy”

Ghetto Cowboy • Slumerican • 2019

Alabama rapper Yelawolf has had his fair share of moments throughout the 2010s, with notable records like “I Just Wanna Party” and “Pop the Trunk” (Trunk Muzik 0-60), “Let’s Roll” (Radioactive), and “Best Friend” (Love Story).  In 2019, he actually released two projects: Trunk Muzik 3 and Ghetto Cowboy.  I bet you can guess what song from Ghetto Cowboy fits the criteria for this cowboy list!

The five-and-a-half-minute “Ghetto Cowboy” concludes Ghetto Cowboy.  Featuring production by Kenneth Pruitt and Brian Jones, it’s dark, set in a minor key, anchored by hard drums.  There’s a heaviness, further propelled by Yelawolf’s profane and unapologetic rhymes.  Case in point:

“Yeah, and now I’m feelin’ great, motherfucker
Prime steak is on the plate, motherfucker
Went from sellin’ that mixtape, motherfucker
To headlinin’, 100K, motherfucker...”

Honestly, Yelawolf could’ve scratched the name “Ghetto Cowboy” in favor of, well, “motherfucker” – he says it enough here.

8. Jon Pardi, “Ain’t Always the Cowboy”

Heartache Medication • Capitol Nashville • 2019

“A tumbleweed heart chasin’ that wind / Goin’ too far, wherever that is.”  Can there be a cowboy-themed playlist without country singers? Of course not.  You could get even more specific and assert that there can’t be a cowboy-themed playlist without Jon Pardi.  Why? Well, his 2016 album, California Sunrise, features the song, “Cowboy Hat.” On his follow-up project, 2019’s Heartache Medication, he brings yet another cowboy song to the fold, “Ain’t Always the Cowboy.”  

“Ain’t Always the Cowboy” is a beautiful, pretty straightforward country ballad. There’s no pop or R&B influence stylistic – this is country music. Cowboys are normally associated with being on the go, but in the case of “Ain’t Always the Cowboy,” Pardi lets the world know that that’s not always the case.  The prime example of this is on the chorus, where he lays out the scenario for us:

“It ain’t always the cowboy
That ain’t got a lot of hang around
Ain’t got no settle down in their boots
Gone’s just what they do
That restless running, searchin’ for something
Leavin’ love in the dust of a midnight Chevrolet
It’ ain’t always the cowboy that rides away.”

According to Pardi (Behind the Song), the song is about “a girl who has her own dreams to chase and ain’t ready to settle down and the cowboy ain’t mad about it.” On the verse, Pardi also emphasizes how he isn’t guilty of “riding away”: “Yeah, it’s hard to believe / It wasn’t me tryin’ to leave this time.”

9. Wiz Khalifa, “Cowboy”

Khalifa • Atlantic • 2016

Wiz Khalifa never had another hit as potent as “Black and Yellow” was.  Sometimes, that’s the way it goes.  By the time his 2016 album, Khalifa, arrived, you could say his popularity had faded a bit.  That’s no disrespect to the project, which has a couple of notable songs, and also delivers another ‘cowboy’ song to our playlist, via “Cowboy.”

 “Cowboy” is slickly produced, thanks to the smooth synths and potent beat by Jim Jonsin and FnZ.  Wiz uses the backdrop to his advantage, spitting easy-going rhymes that still pack a punch.

“Just a young lil nigga, but he had the right plan
Twenty thousand in his left, pistol in his right hand
Counting every dolla that he get, cause he worked for it
But don’t run up on hmi cause you’ll probably get murked for it.”

Okay! Essentially, the record paints Wiz as a “Midwest cowboy, Pittsburgh nigga / Came from a city where the niggas they some killas.”  Fair enough.  Even as simple as it may be, if nothing else, the chorus is quite catchy.

10. Mac DeMarco, “Here Comes the Cowboy”

Here Comes the Cowboy • Mac’s Record Label • 2019

In 2019, singer/songwriter Mac DeMarco dropped a new album, Here Comes the Cowboy.  Fittingly, for the Fittingly, for the indie/alternative artist, the title track commences the affair.  Three minutes in duration, “Here Comes the Cowboy” features only one lyric: “Here comes the cowboy.” Yes, I’m dead serious – minimalism is in full effect.

So, besides one lyric, what else does Mac DeMarco give us on “Here Comes the Cowboy.” Well, he’s expressive as he sings the sole lyric that’s repeated throughout the record, so there’s that.  Also, the backdrop has a country/folk sensibility, fitting for any song about cowboys.  The music itself (guitar, drums), like the lyrics, loops over and over, in hypnotic fashion.  There is a colorful, accompanying music video, if you can believe it or not! Honestly, that’s about the size of “Here Comes the Cowboy.”