Songfacts®:

• Woody Guthrie was an incredibly prolific songwriter, composing thousands of songs in his lifetime. Many of these, like "The Sinking Of The Reuben James," were based on events that Guthrie read about in news articles. It's likely that Guthrie came across the story of an outlaw named Pretty Boy Floyd, which provided material for this song. Anna Canoni, who is Guthrie's granddaughter, explains: "'Pretty Boy Floyd' is one of Woody's more popular ballads. The outlaw who helped the poor, a Robin Hood story. What Woody would do, he would take newspapers read through the articles and write songs about stories that touched him. Being able to write powerful stories about an event I think that that's such an amazing gift that Woody could bring to songwriting." (Anna is a director at the Woody Guthrie Foundation and Archives. Read more in her full interview. Learn much more at the official Woody Guthrie website.)
• Some of the artists to record this song: Joan Baez, The Byrds, Bob Dylan, Ramblin' Jack Elliott, Country Joe McDonald and Pete Seeger. In a 1975 interview with Let It Rock, Roger McGuinn of The Byrds said: "I love 'Pretty Boy Floyd.' It's very typical, that killer-outlaw as hero, just because during the depression, banks were considered more the enemy than the people who robbed them. A few killings here and there were allowed."