The Best Sad Country Songs

A selection of country music's finest tearjerkers

Holler - The Best Sad Country Songs,


It’s like Dolly always says: “If you want the rainbow, you gotta put up with the rain”

link icon

Link copied

Apple Music
Amazon Music
YouTube Music

If you’re feeling particularly fed up today, don’t worry. You won’t be alone in feeling blue. We all have off days; those when it feels like a little black cloud is following us everywhere we go, making everything gloomy and miserable.

Life isn’t always blue skies and puppy dogs, and sometimes it’s a whole lot of hard work just getting through the day. But if we were happy all the time we wouldn’t need sad songs, and sad songs are some of the greatest songs in the whole world - especially in country.

Sometimes the best thing to do is wallow in all that misery and make a day of it; sit under that rain cloud and just enjoy getting absolutely soaked. It’s like Dolly always says: “If you want the rainbow, you gotta put up with the rain”.

So sit back and indulge in the tearjerking tones of Holler’s Best Sad Country Songs playlist. Let Willie and Dolly take it from here. We can all try again tomorrow.

Full Track Listing:

1. Blue Eyes Crying In the Rain - Willie Nelson

2. Hurt - Johnny Cash

3. I'm So Lonesome I Could Cry - Hank Williams

4. He Stopped Loving Her Today - George Jones

5. I Drive Your Truck - Lee Brice

6. Drink A Beer - Luke Bryan

7. I Miss My Friend - Darryl Worley

8. Whiskey Lullaby - Brad Paisley, Alison Krauss

9. Remembering - Ashley Campbell

10. If You're Reading This - Tim McGraw

11. You Should Be Here - Cole Swindell

12. Rosewood Casket - Dolly Parton, Linda Ronstadt, Emmylou Harris

13. I Fall To Pieces - Patsy Cline, The Jordanaires

14. Old Shep - Red Foley

15. Dawn From Dover - Nancy Sinatra, Lee Hazlewood

16. For the Good Times - Ray Price

17. Three Wooden Crosses - Randy Travis

18. The Long Black Veil - Lefty Frizzell

19. Me and Little Andy - Dolly Parton

20. Hello Walls - Faron Young

21. She Thinks His Name Was John - Reba McEntire

22. Go Rest High On That Mountain - Vince Gill

23. Bottle by My Bed - Sunny Sweeney

24. If We Were Vampires - Jason Isbell and the 400 Unit

25. I Remember Everything - John Prine

26. Just a Dream - Carrie Underwood

27. Where've You Been - Kathy Mattea

28. Bring My Flowers Now - Tanya Tucker

29. Tonight I Wanna Cry - Keith Urban

30. Waiting Around to Die - Townes Van Zandt

31. Life Turned Her That Way - Ricky Van Shelton

32. Heaven's Only Days Down the Road - Shelby Lynne

33. The Last Word In Lonesome Is Me - Roger Miller

34. Why - Rascal Flatts

35. Chiseled In Stone - Chris Young

36. The Little Girl - John Michael Montgomery, Alison Krauss, Dan Tyminski

37. Concrete Angel - Martina McBride

38. Every Time I Hear That Song - Brandi Carlile

39. Holes In The Floor Of Heaven - Steve Wariner

40. If Something Should Happen - Darryl Worley

Subscribe and listen to Holler's The Best Sad Country Songs Playlist above.