15 songs, 44 min, 3 min reading time.

For those of us who love cowboy music but also have the blues.

Author: Rory

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1) “On The Road Again” – Canned Heat

A great Canned Heat song, especially considering their other most famous song is so upbeat.

Album: “The Best Of Canned Heat” (1987)

Label: Capitol Records

2) “Born To Lose” – Ted Daffan And His Texans

Found from the game ‘getting over it with Bennett Foddy’. Spongebob vibes.

Compilation: “The Best Of Western Swing” (2011)

Label: KCP

3) “Lungs” – Townes Van Zandt

Great song from a talented guitar player who sadly died too young. Found on season 1 of “True Detective.”

Album: “The Best of Townes Van Zandt” (2018)

Label: Fat Possum Records

4) “Dark as the Dungeon – Live at Folsom State Prison, Folsom, CA – January 1968” – Johnny Cash

Never been a coal miner but still somehow resonates.

Album: “At Folsom Prison” (1968)

Label: Sony Music Entertainment

5) “Not in My League” – Sun City Girls

Never understood this song, but eerie at the very least.

Album: “Carnival Folklore Resurrection Vol 11/12: Radio One & Two” (2012)

Label: Sun City Girls

6) “The Long Black Veil” – Lefty Frizzell

Good guitar even better storytelling.

Album: “Look What Thoughts Will Do” (1997)

Label: SONY BMG MUSIC ENTERTAINMENT

7) “Blue Eyes Crying In the Rain” – Willie Nelson

No Sad Cowboy Music playlist would be complete without Willie Nelson.

Album: “Red Headed Stranger” (1975)

Label: Sony Music Entertainment

8) “Long Gone Lonesome Blues – Single Version” – Hank Williams

Incredibly yodelling. Not a sentence I thought I would ever write.

Album: “40 Greatest Hits” (1978)

Label: UMG Recordings

9) “Nobody’s Lonesome For Me – Single Version” – Hank Williams

Hard violin.

Album: “40 Greatest Hits” (1978)

Label: UMG Recordings

10) “They’ll Never Take Her Love From Me – Single Version” – Hank Williams

My boy Hank yet again tugging at heartstrings.

Album: “40 Greatest Hits” (1978)

Label: UMG Recordings

11) “Dear John – Single Version” – Hank Williams

Maybe my favourite country heartbreak song ever. Happy tune but about waking up to find your wife left you, what juxtaposition.

Album: “40 Greatest Hits” (1978)

Label: UMG Recordings

12) “Blue Skies” – Willie Nelson

The only version that ever compares to Ella Fitzgerald’s.

Album: “Stardust” (1978)

Label: Sony Music Entertainment

13) “Truckin’ My Blues Away” – Blind Boy Fuller

Shown to me by my dear friend Felix. Maybe not necessarily sad but at least melancholy.

Album: “Blind Boy Fuller Vol. 1 1935 – 1936” (1992)

Label: Document Records

14) “Hang Me, Oh Hang Me” – Dave Van Ronk

Sad but lovely song and a fantastic voice to beat.

Album: “Folksinger” (1989)

Label: Fantasy

15) “Kentucky Moonshine” – Pure Prairie League

It’s not cowboy music without drinking yourself blind on moonshine.

Album: “Two Lane Highway” (1993)

Label: BMG