"I'm So Lonesome I Could Cry" is a song that's so iconic, I'd be shocked if someone doesn't know it. Elvis Presley said it was the saddest song he'd ever heard and it's certainly in the top 5.
Hank Williams wrote and recorded the song in 1949. His straightforward singing, poetic lyrics and hummable tune made the song an instant classic. You can really hear the pain in his voice.
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(By the by, if you have any interest in country music at all, I highly recommend a Hank Williams greatest hits album. I personally like 40 Greatest Hits.)
This song has gone on to be covered by hundreds of singers with many different interpretations. As it so happens, I own quite a few different versions.
In 1973 Al Green did a smooth soul version included on his seminal album "Call Me." I love what he does with the song here.
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The Cowboy Junkies did a version on their 1988 Trinity Sessions album. By far, the slowest version. Very haunting. This album also includes a cover of Lou Reed's Sweet Jane, another song done by a multitude of singers.
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Jimmie Dale Gilmore is an alternative country singer. His 1993 version is the closest to the original, although the guitar work is very different. From the album Spinning Around the Sun.
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Cassandra Wilson's jazz inflected version is included on her '95 New Moon Daughter album.
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And finally, Johnny Cash dueting with Nick Cave on American IV: The Man Comes Around (2002). I highly recommend the entire American series. Impeccable song selections and Cash's interpretations are outstanding.
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So, six very different versions. There are hundreds more, but these are the ones I own. If you own a different take, post it below.