"I’m So Lonesome I Could Cry" by Hank Williams Sr., contributed by Audrey Moorhead (2023)
Williams was known for his direct yet sophisticated lyrics, as exemplified in one of his best-known songs, “I’m So Lonesome I Could Cry.” The song has been covered by countless artists across generations and genres, and songwriters still pay homage to Williams by referencing the iconic opening line: “Hear that lonesome whippoorwill / He sounds too blue to fly.” The natural imagery throughout the song perfectly encapsulates the speaker’s desolation after the loss of his lover and the universal quality of the speaker’s loss.