20 Saddest Country Songs of All Time

Here’s the un-authoritative and absolutely subjective list of the twenty saddest country songs of all time (ranked from most to least likely to elicit that eye-watering physiological response):

  1. Conway Twitty “That’s My Job”

2. Johnny Cash “Hurt”

3. Alan Jackson “Remember When”

4. Sawyer Brown “The Walk”

5. Merle Haggard “Sing Me Back Home”

6. Clink Black “A Bad Goodbye” ft. Wynonna

7. Tammy Wynette “’Til I Can Make it On My Own”

8. Loretta Lynn “Lay Me Done” ft. Willie Nelson

9. Emmylou Harris “Boulder to Birmingham”

10. Dolly Parton “The Grass is Blue”

11.George Jones “Choices”

12. Tim McGraw “Don’t Take the Girl”

13. Mary Gauthier “Mercy Now”

14. Tany Tucker “Bring My Flowers Now”

15. Keith Whitley “Don’t Close Your Eyes”

16. Travis Tritt “Anymore”

17. Dolly Parton “Me and Little Andy”

18. Brad Paisley “Whiskey Lullaby” ft Alison Krauss

19. Allison Kraus and the Union Station “The Captain’s Daughter”

20. Darrell Scott “You’ll Never Leave Harlan Alive”

Honorable Mentions and Suggestions (please send them my way):


Here’s the playlist on Spotify:


If you enjoyed this list, here are some others:

Thanks. – shawn


Photo by Markus Spiske on Unsplash