Bob Dylan's first national TV appearance came in March of 1963 on a program called "Folk Songs, and More Folk Songs!" He performed three songs, including "Man of Constant Sorrow," a folk tune from circa 1913, originally recorded by the partially blind fiddler Dick Burnett. Burnett, interviewed late in life, couldn't remember whether he had written the tune, saying: "No, I think I got that ballad from somebody. I dunno. It may be my song." Wikipedia comments on the uncertainty around the song's origins:
If Burnett wrote the song, the date of its composition, or at least of the editing of certain lyrics by Burnett, can be fixed at about 1913. Since it is known that Burnett was born in 1883, married in 1905, and blinded in 1907, the dating of two of these texts can be made on the basis of internal evidence. The second stanza of "Farewell Song" mentions that the singer has been blind six years, which put the date at 1913. According to the Country Music Annual, Burnett "probably tailored a pre-existing song to fit his blindness" and may have adapted a hymn. Charles Wolfe argues that "Burnett probably based his melody on an old Baptist hymn called 'Wandering Boy.'
The song became popular for at least the third time after the 2000 film O Brother, Where Art Thou? which positioned it as a hit for the "Soggy Bottom Boys." Between its original recording, the Dylan performance, and the O Brother resurgence, it was also recorded by the Stanley Brothers, Judy Collins, Waylon Jennings, Rod Stewart, Jerry Garcia, and Jackson Browne among many others. Like most folk songs, this tune gets around. Here are some landmark performances.
Bob Dylan, 1963
21 years old, folks.
Soggy Bottom Boys
The vocal here is not performed by Clooney; it's bluegrass master Dan Tyminski.
Alison Krauss & Union Station (ft. Dan Tyminski)
Okay, so let's see Tyminski in action:
The Soggy Bottom Boys (ft. Everybody Ever)
From the Grammies, 2002. Just settle back and enjoy.
New Lost City Ramblers
undated c. 1965 Rainbow Quest performance is roughly contemporaneous with the Dylan performance, though I'll leave it up to you to decide which one has more soul.