"When I Was a Cowboy" is a cowboy song that was collected from black cowboys in south Texas. It was not uncommon in the early days of the cattle industry in east Texas for black cowboys to be included in cattle outfits. Alan Lomax finds it to be a combination of a cowboy song called "Longhorn Cows" and the British ballad "Five Nights Drunk", also known as "Our Goodman". The Lomax version of this song comes from Lead Belly and the Fife versions derive from Lomax. So it's not clear how much of this is truly traditional and how much Lead Belly. It was printed in Alan Lomax's The Folk Songs of North America (1960), John A. Lomax and Alan Lomax's American Ballads and Folk Songs (1934), Austin E. and Alta S. Fife, Cowboy and Western Songs (1969) and Moses Asch and Alan Lomax's The Leadbelly Songbook (1962). It is #3438 in the Roud index. It was recorded by Ian & Silvia on Play One More (1966).