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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." ...

Singer/songwriter Phoebe Bridgers is a modern-day indie-folk master of the melancholy, and these four songs are some of her most heartwrenching works. This list is not exhaustive, either.