The Best Sad Country Songs Playlist

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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.

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

1. 1.

   Blue Eyes Crying In The Rain

   Willie Nelson

2. 2.

   Hurt

   Johnny Cash

3. 3.

   I'm So Lonesome I Could Cry

   Hank Williams

4. 4.

   He Stopped Loving Her Today

   George Jones

5. 5.

   I Drive Your Truck

   Lee Brice

6. 6.

   Drink A Beer

   Luke Bryan

7. 7.

   I Miss My Friend

   Darryl Worley

8. 8.

   Whiskey Lullaby (Feat. Alison Krauss)

   Brad Paisley

9. 9.

   Remembering

   Ashley Campbell

10. 10.

    If You're Reading This

    Tim McGraw

11. 11.

    You Should Be Here

    Cole Swindell

12. 12.

    Rosewood Casket (Feat. Linda Ronstadt & Emmylou Harris)

    Dolly Parton

13. 13.

    I Fall To Pieces (Feat. The Jordanaires)

    Patsy Cline

14. 14.

    Old Shep

    Red Foley

15. 15.

    Down From Dover (Feat. Lee Hazlewood)

    Nancy Sinatra

16. 16.

    For The Good Times

    Ray Price

17. 17.

    Three Wooden Crosses

    Randy Travis

18. 18.

    The Long Black Veil

    Lefty Frizzell

19. 19.

    Me And Little Andy

    Dolly Parton

20. 20.

    Hello Walls

    Faron Young

21. 21.

    She Thinks His Name Was John

    Reba McEntire

22. 22.

    Go Rest High On That Mountain

    Vince Gill

23. 23.

    Bottle By My Bed

    Sunny Sweeney

24. 24.

    If We Were Vampire

    Jason Isbell And The 400 Unit

25. 25.

    I Remember Everything

    John Prine

26. 26.

    Just A Dream

    Carrie Underwood

27. 27.

    Where've You Been

    Kathy Mattea

28. 28.

    Bring My Flowers Now

    Tanya Tucker

29. 29.

    Tonight I Wanna Cry

    Keith Urban

30. 30.

    Waiting Around To Die

    Townes Van Zandt

31. 31.

    Life Turned Her That Way

    Ricky Van Shelton

32. 32.

    Heaven's Only Days Down The Road

    Shelby Lynne

33. 33.

    The Last Word In Lonesome Is Me

    Roger Miller

34. 34.

    Why

    Rascal Flatts

35. 35.

    Chiseled In Stone

    Chris Young

36. 36.

    The Little Girl (Feat. Alison Krauss)

    John Michael Montgomery

37. 37.

    Concrete Angel

    Martina McBride

38. 38.

    Every Time I Hear That Song

    Brandi Carlile

39. 39.

    Holes In The Floor Of Heaven

    Steve Wariner

40. 40.

    If Something Should Happen

    Darryl Worley