Playlist

The Best Sad Country Songs Playlist

It’s like Dolly always says: “If you want the rainbow, you gotta put up with the rain”. From Willie Nelson to Darryl Worley, Holler picks the 40 best sad country songs.

Holler Country Music

It’s like Dolly always says: “If you want the rainbow, you gotta put up with the rain”. From Willie Nelson to Darryl Worley, Holler picks the 40 best sad country songs.

January 17, 2022 12:31 pm GMT
Last Edited June 30, 2023 10:17 am GMT

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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

Written by Jof Owen
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