5 of the Saddest Country Storytelling Songs That Always Bring a Tear to My Eye

No musical genre does sad storytelling songs quite as well as country, and there’s no shortage of songs to prove that point. Whether they’re songs about heartbreak or death or losing a job or maybe even a mix of all three, country songs have a way of cutting right to the bone. And in this weepy writer’s humble opinion, there are no sad country storytelling songs quite as sad and tear-jerking as these five.

“El Paso” by Marty Robbins

Marty Robbins’ voice alone is beautiful enough to make you cry. Add a devastating storyline like “El Paso”, and tears are almost a certainty. This song follows a traditional ballad format, outlining the characters and events that eventually lead to the climax. It’s a classic story of a love that goes wrong. A jealous lover kills another man and becomes a wanted criminal. He flees town, but the pain of being apart from his lover is too much. When he tries to return to see her, he’s shot off his horse and dies in her arms. Tears. Every time.

“Pancho And Lefty” by Townes Van Zandt

“Pancho And Lefty” by Townes Van Zandt is the kind of story that makes you feel bad for the antagonist, which is no small feat. The song heavily implies that Lefty sold out his criminal partner, Pancho, in exchange for his own freedom—and a little bit of cash. When Pancho died in a shootout with the Federales, Lefty was running off to Ohio. “Where he got the bread to go, nobody knows.” Still, the lonely, desolate life of Lefty, a man who will forever have that guilt hanging over his head, is no less saddening.

“Hello In There” by John Prine

John Prine wrote “Hello In There” about the way life changes in old age, both in the way that we perceive it and the way others perceive us. He wrote the song after being inspired by older people he met on his mail route, and the result is a stunningly sad country song that brings me to tears every time I listen. “You know that old trees just grow stronger, and old rivers grow wilder every day / Old people just grow lonesome waiting for someone to say, ‘Hello in there, hello.’”

“Whiskey Lullaby” by Brad Paisley and Alison Krauss

Honestly, it wouldn’t be a sad country song list that I wrote if it didn’t include “Whiskey Lullaby”. I consider this Brad Paisley and Alison Krauss duet one of the saddest songs of all time, let alone in the storytelling country category specifically. The idea of two people breaking apart after someone’s affair and it killing them both is one of the bleakest, most desolate situations one could imagine in a relationship. The gentle way the country stars deliver the storyline makes it that much sadder.

“Travelin’ Soldier” by The Chicks

“Travelin’ Soldier” by The Chicks (then The Dixie Chicks) came out around the same time as “Whiskey Lullaby”. Needless to say, we were deep in our feelings in the early 2000s. The Chicks’ ballad about a Vietnam soldier falling in love with a waitress just before his deployment, dying in the war, and the waitress crying under the bleachers while his name is said over the loudspeaker in a list of overseas deaths is just heartbreaking. There’s no other way to put it.

Photo by Andrew Putler/Redferns