Without a doubt, Hank Williams’ “I’m So Lonesome I Could Cry” has one of the most lovesick lyrics in all of country music. 

“I’m So Lonesome I Could Cry” was released as a mere B-side to the up-tempo “My Bucket’s Got a Hole in It” because it was deemed more radio-friendly than melancholy ballads. Still, the single reached No. 4 on the country chart in 1949.

The song has then become closely identified with Williams’s musical legacy and has been widely praised. In the documentary The Road to Nashville in 2003, singer k.d. lang said, “‘I think ‘I’m So Lonesome I Could Cry'” is one of the most classic American songs ever written, truly. Beautiful song.”

On the other hand, Bob Dylan recalled in his autobiography, “Even at a young age, I identified with him. I didn’t have to experience anything that Hank did to know what he was singing about. I’d never heard a robin weep, but could imagine it, and it made me sad.”

Rolling Stone ranked “I’m So Lonesome I Could Cry” No. 111 on their list of the 500 Greatest Songs of All Time – it’s the oldest song on that list. It was also ranked No. 3 on Rolling Stone’s 100 Greatest Country Songs of All Time.

The Story Behind The Most Lonesome Song Ever Played in Country Radio

“I’m So Lonesome I Could Cry” was one of many songs Hank Williams wrote to express his crippling sadness. His tumultuous relationship inspired most of these songs with his first wife, Audrey Sheppard.

“Hear that lonesome whippoorwill; he sounds too blue to fly. That midnight train is whining low. I’m so lonesome I could cry. I’ve never seen a night so long When time goes crawling by. The moon just went behind a cloud To hide its face and cry,” the song goes.

Williams recorded the song at Herzog Studio in Cincinnati, Ohio, on a late summer day of 1949, as he approached his 26th birthday. But did you know Williams originally wrote “I’m So Lonesome I Could Cry” as a spoken-word piece? The country legend planned to record the song as his alter-ego, “Luke the Drifter,” which explains why it contained very poetic imagery in lines such as “Did you ever see a robin weep when leaves begin to die?” 

Williams thought the piece was too discreet to put music, but he was urged by his friends and fellow musicians to add a melody. The song quickly became a favorite on country radio and a staple of Hank Williams’ live shows. It’s been covered a numerous amount of times. Glen Campbell, Bob Dylan, Johnny Cash, Elvis Presley, and Tanya Tucker are some more notable versions.

But nobody does it better than the legend himself, Hank Williams. Singing the heartbreaking “I’m So Lonesome I Could Cry,” he showed off his ability to channel the right emotions necessary to sing this heart-wrenching song. Watch it in the video below.