"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. During his Aloha from Hawaii TV-special, Elvis Presley introduced it by saying, "I'd like to sing a song that's...probably the saddest song I've ever heard."

According to Colin Escott's 2004 book Hank Williams: A Biography, Williams was inspired to write the song when he found it on a schedule of upcoming MGM releases. The song was recorded on August 30, 1949 at Herzog Studio in Cincinnati, Ohio. Williams is backed by members of the Pleasant Valley Boys - Zeke Turner (lead guitar), Jerry Byrd (steel guitar), and Louis Innis (rhythm guitar) - as well as Tommy Jackson (fiddle) and Ernie Newton (bass). As Escott observes, the plaintive despair in Williams' voice on the recording is echoed by the backing of the musicians:

Remarkably, the song was released as the B-side to the blues "My Bucket's Got a Hole in It" because up-tempo numbers were deemed more appropriate for the jukebox trade than melancholy ballads. The single reached #4 on the country chart in 1949. The song has become closely identified with Williams' legend and musical legacy and has been widely praised. In the 2003 documentary The Road to Nashville, singer k.d. lang states, "I think 'I'm So Lonesome I Could Cry' is one of the most classic American songs ever written, truly. Beautiful song." In his autobiography, Bob Dylan recalls, "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." In its online biography of the singer, Rolling Stone notes, "In tracks like 'I'm So Lonesome I Could Cry' Williams expressed intense, personal emotions with country's traditional plainspoken directness, a then-revolutionary approach that has come to define the genre through the works of subsequent artists from George Jones and Willie Nelson to Gram Parsons and Dwight Yoakam." Rolling Stone ranked it #111 on their list of the 500 Greatest Songs of All Time, the oldest song on the list, and #3 on its 100 Greatest Country Songs of All Time.

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