36. I’m So Lonesome I Could Cry – Hank Williams – 1949






“”I’m So Lonesome I Could Cry” is a song written and recorded by American country music singer-songwriter Hank Williams in 1949. Williams wrote the song originally intending that the words be spoken, rather than sung, as he had done on several of his Luke the Drifter recordings. 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 whip-poor-will/He sounds too blue to fly,” the song has been covered by a wide range of musicians.


  • Rolling Stone ranked it #111 on their list of the 500 Greatest Songs of All Time, the oldest song on the list.
  • It was released as the b-side to the #2 Billboard Country single “My Bucket’s Got a Hole in It”.
  • Regarded as one of the most significant country music artists, Williams recorded 35 singles (five released posthumously) that would place in the Top 10 of the Billboard Country & Western Best Sellers chart, including 11 that ranked number one.
  • Williams died in the early morning hours of New Years Day in 1953 at the age of 29 from heart failure exacerbated by pills and alcohol. Despite his short life, Williams has had a major influence on twentieth century popular music.

2 responses »

  1. This was a B side? Ermagerd. Sometimes it’s the stuff that no one expects that goes onto greatness it seems. Again, this is sort of underlining all that is country in 3 minutes, slower pace, use of folk or classical instruments, uncomplicated rhythm and of course devastatingly earnest lyrics. Knowing now what we know about Williams it kind of taints all his music with a different tone, much like Nirvana in the wake of Kurt’s suicide. It takes what is a song written by a writer into a snapshot of a troubled life that we now know is actually quite authentic, which has become the basis for country, rock and even hip-hop. It seems people want the artist to live their lyrics or they’re a fake. Unless they’re Bruce Springsteen who sings for the working class and never worked a day in his life hahaha

  2. I know! I love it when they miss the mark with a song so remarkably!
    I’d be interested to know if it was the appeal of this song which drove the sales of the single, given that it got to #2, but it’s the b-side that lasted.
    I’ve never been a big fan of Country, but I actually enjoyed this. I’d like to hear some more of this early Country music.

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