First recorded by Dick Burnett (as “Farewell Song” c. 1913), Emry Arthur (1928).
Hit versions by The Stanley Brothers (1951 | 1959), Ginger Baker’s Air Force (C&W #36/UK #86 1970), Soggy Bottom Boys (C&W #35 2000).
Also recorded by Judy Collins (as “Maid of Constant Sorrow”) (1961), Bob Dylan (1962), Jerry Garcia (1993).
From the wiki: “‘Man of Constant Sorrow’ (also known as ‘I Am a Man of Constant Sorrow’) is a traditional American folk song first recorded in 1913 by Dick Burnett, a partially blind fiddler from Kentucky, who published the song as ‘Farewell Song’. (Some uncertainty exists as to whether Burnett himself wrote the song. One claim is that it was sung by the Mackin clan in 1888 in Ireland and that Cameron O’Mackin emigrated to Tennessee, bringing the song with him.) Another early version was commercially released by Emry Arthur in 1928.