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  1. Flip through the slideshow below for 20 of country's saddest songs, from classics like "I'm So Lonesome I Could Cry" to newer songs like Jason Isbell's "Dress Blues."

  2. One of the most iconic and heart-wrenching songs in country music is “Im So Lonesome I Could Cry” by Hank Williams. This classic tune captures the raw emotion of loneliness and heartbreak in a way that resonates with listeners decades after its release.

  3. 10 Ιαν 2024 · Get ready to choke back some tears—we've gathered our favorite sad country songs that are virtually impossible to get through without crying.

  4. 5 Απρ 2022 · These story-songs have the power to make us cry, but many of them also offer comfort and hope for a brighter tomorrow. So whenever you're in need of a good cathartic cry, throw on this playlist of the saddest country songs.

  5. 9 Απρ 2018 · If you feel like a good cry, we made a playlist of the saddest country love songs we could find. Listen to our Spotify playlist below, and fair warning: there will be tears. "Whiskey...

  6. 13 Ιουλ 2024 · Each one of the 50 saddest country songs of all time tells a story. Some of those stories are about the pain of heartbreak, while others explore the grief of losing a loved one.

  7. 23 Σεπ 2024 · Country music tells it how it is, with straight-up songwriting power and a depth to the genre you would be hard-pressed to find coming from anywhere else. Here are 15 heart-breaking country songs that will make you Frances. Brad Paisley (Feat. Alison Krauss) — “Whiskey Lullaby”.

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