Readers' Poll: The 10 Saddest Songs of All TimeYour picks include 'Cat's in the Cradle and 'I'm So Lonesome I Could Cry'
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10. Hank Williams - 'I'm So Lonesome I Could Cry'
Three years before he died, Hank Williams poured out all the pain from his failing marriage to his wife Audrey Sheppard into this masterpiece. Williams wrote hundreds of songs and scored many huge hits during his brief life, but this is one of the few you still hear all the time, all these decades later. That's probably because the message is so universal and his raw pain is impossible to ignore. It's since been covered by everybody from Elvis Presley to Johnny Cash to Yo La Tengo.