This is the last song on Bob Dylan's second album, The Freewheelin' Bob Dylan
. It's a rewrite of Leadbelly's "We Shall Be Free," which was recorded with Woody Guthrie and Sonny Terry in 1944. Dylan admired all of these singers, but Guthrie was his early idol. In 1961, when Guthrie was hospitalized with Huntington's disease in Greystone Park Psychiatric Hospital in New Jersey, Dylan visited him
(Dylan's visits were to an apartment nearby where Guthrie spent his Sundays as an outpatient). Two years later, Dylan released a song called "Last Thoughts on Woody Guthrie
" in tribute (Guthrie died in 1967).
The roots of "I Shall Be Free" go even further back than that 1944 song, though. In his essay "Don't Leave Me Here: Non-Commercial Blues: The Field Trips, 1924–1960" (included in Nothing but the Blue: The Music and Musicians
, edited by Lawrence Cohn), John H. Cowley traces the song back as far as the mid-19th century. Cowley reveals the song, like most early American songs, to have been the evolution of many earlier songs.
Dylan's particular version is a satirical talking blues song about a drunk who gets called by the president and is asked for advice on how to make the country better. There's more to it than that, but the whole thing is so winding and absurd that trying to pin down exactly what it's about ends up sounding equally winding and absurd.
There may be more than humor at play here, though. In his early career, Dylan made his name with political songs and was taken on as a sort of political mascot by the progressive intellectual crowd of the day.
In the song, President Kennedy asks Dylan, who plays the character of a hard-drinking and irrational man, "My friend, Bob, what do we need to make the country grow?" This may be Dylan poking fun at his own status or the people conferring that status upon him (or both).
The song also may be making fun of politics in general, as indicated in the verse: Now, the man on the stand he wants my vote
He's a-runnin' for office on the ballot note
He's out there preachin' in front of the steeple
Tellin' me he loves all kinds-a people
(He's eatin' bagels
He's eatin' pizza
He's eatin' chitlins
He's eatin' bulls--t!)
Or maybe Dylan is having fun with all this while also making a point about the absurdity of politics.