Making a list of 10 country sad songs is almost just like making a list of country songs; almost all of the best country songs are sad about something or other, be it heartbreak, the loss of a loved one, or just plain drinking too much the night before. There are way too many great country sad songs to whittle it down to a definitive list, but our 10 country sad songs are as good a place to start as any, spanning different eras and reasons for sadness.
- "Long Black Veil" by Johnny Cash – "Long Black Veil" has been performed by many artists, but the Man in Black's definitive version tops our list of country sad songs. A story of death and betrayal, it is a haunting leader for our list.
- "Heartaches by the Number" by Dwight Yoakam – A traditional "tears in the beer" weeper from Dwight was a highlight of his debut album. Yoakam has recorded many other country sad songs throughout a decades long career.
- "You'll Never Leave Harlan Alive" by Brad Paisley – A traditional song about the travails of coal miners in Kentucky, "Harlan" was reworked by Brad Paisley and given new life. It's not about heartache, but it is one of the best country sad songs of the past twenty years.
- "Short Side of Nothing" by Los Lobos – Los Angeles' premier everything-in-a-blender band has mastered country as well as Mexican musical styles and rockabilly, among others. "Nothing" is a country sad song from their album "Kiko."
- "I Fall to Pieces" by Patsy Cline – Patsy Cline's shortened life was like a country sad song. If any of her tunes could define that, it would be "I Fall to Pieces," possibly her definitive record.
- "A Little Bit Lonesome" by Kasey Chambers – This Australian songstress broke through to aficionados of country sad songs with this tune from her album "Barricades and Brickwalls." Her girlish voice trembles with pain in this heartache song.
- "Blue" by Ryan Adams – A little-heard song from Adams' unreleased masterpiece "48 Hours," "Blue" has Ryan singing like Roy Orbison, the master of heartbreak. It is one of the best country sad songs of the 2000s.
- "Sunday Mornin' Comin' Down" by Kris Kristofferson – A mournful, regretful hangover song, Kristofferson's enduring classic belongs on any list of country sad songs. It was also covered by Johnny Cash.
- "Angel of Death" by Hank Williams – Sadness gives way to resignation in this haunting gospel song from the early master, Hank Senior. It is probably his gospel masterpiece.
- "Alone and Forsaken" by Hank Williams – Hank's secular masterpiece closes out the list of 10 country sad songs. The title says it all.
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