What's not in question was that amid the pain of the Depression, Floyd earned a romantic reputation as a latter-day Robin Hood. He was lauded for helping out downtrodden families with his ill-gotten gain, buying them food, paying mortgages, etc. It earned him a mythical populist reputation in the 1930's, a time banks those who ran them were seen as cruel, greedy and unfeeling.
Among those who mythologized him was was Woody Guthrie, a son of Oklahoma. He chronicled the deeds of a number of individuals considered outlaws and in March of 1939 wrote "The Ballad of Pretty Boy Floyd," recording it twice in 1940, one for what became his famous Dust Bowl Ballads album and again that that year for the Library of Congress.
This is the Dust Bowl Ballads version.
The Byrds recorded a bluegrass version on their 1968 Sweetheart Of The Rodeo album, recorded in Nashville. Roger McGuinn did the vocals but had trouble playing the banjo parts, so John Hartford came in and overdubbed banjo, guitar and fiddle. The mandolinist is Byrds bassist Chris Hillman. considered a top West Coast bluegrass mandolinist in his pre-Byrds days. Nashville studio musician Junior Husky handled the upright bass.
A number of individuals recorded it over the years, among them Woody's friend Ramblin' Jack Elliott, Joan Baez and Arlo Guthrie. Bob Dylan, who built his early sound on Guthrie's, recorded this version in 1988 for the album Folkways: A Vision Shared A Tribute To Woody Guthrie and Leadbelly.