“I’m So Lonesome I Could Cry” was written by Hank Williams and recorded by Hank Williams and his Drifting Cowboys at Herzog Studio in Cincinnati on August 30, 1949. It was released by MGM in late 1949 as the B-side of “My Bucket’s Got a Hole in It,” and is widely regarded as one of the most enduring lyrics in 20th-century American popular music. Rolling Stone ranked it No. 100 on its 2004 list of the 500 greatest songs of all time.
The lyric works through a series of poetic loneliness images — the whippoorwill too blue to fly, the midnight train whining low, the moon hiding its face — that pull country songwriting into the territory of older Anglo-American ballad poetry. Williams reportedly told his stepson the song was written about his troubled marriage to Audrey Williams during the period leading up to their separation.
The song crossed into the bluegrass repertoire almost immediately. B.J. Thomas’s 1966 cover charted at No. 8 on the country chart and No. 22 on the Hot 100. Bluegrass acts from the Stanley Brothers through the Lonesome River Band have covered it, and it remains one of the most-called slow vocal pieces in the modern roots-music canon. It works as a slow feature in any acoustic set with a strong harmony slot on the chorus.
