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"I'm So Lonesome I Could Cry" is a song written and recorded by American country music singer-songwriter Hank Williams in 1949. The song about loneliness was largely inspired by his troubled relationship with wife Audrey Sheppard. With evocative lyrics, such as the opening lines "Hear that lonesome whippoorwill/He sounds too blue to fly," the song has been covered by a wide range of musicians. Among those who have recorded the song following Williams' death include Johnny Cash with Nick Cave, Ray Charles, Al Green, B.J. Thomas, Cassandra Wilson, Freddy Fender and The Raveonettes. Cowboy Junkies covered the song on their famous The Trinity Sessions album. Elvis Presley did a version of the song in his popular Aloha from Hawaii TV-special. In the D.A. Pennebaker documentary Don't Look Back Bob Dylan is seen playing the song for friends. The punk rock cover band Me First and the Gimme Gimmes has covered this song for their 2006 country-themed album Love Their Country.
Rolling Stone ranked it #111 on their list of the 500 Greatest Songs of All Time. It's the second oldest song on the list, and one of only two from the 1940s.
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