3. Hank Williams, ‘I’m So Lonesome I Could Cry’ (1949)
The original song remains as one of pop music’s most masterfully executed cries of emotion. Williams mourns his failing marriage to wife Audrey, revealing a series of deathly images like a whippoorwill too blue to fly, the moon hiding behind the clouds, and a falling star silently lighting up a purple sky.
Source: Rolling Stone
Those images ride on the melody until the singer sums it all up by saying that he’s “lost the will to live.” Nearly four years later, Williams was found dead in his Cadillac on New Year’s Day. So, it’s also the context that makes this song as impactful as it is.