In spirit, "I Shall Be Free No. 10" is a continuation of "I Shall Be Free
," which appeared on Freewheelin' Bob Dylan
one year and two albums before this song's release. That one is an interpretation of a 1944 song which itself was traced through history as far back as the mid-19th century. Dylan seems to be recognizing this history by adding the "No. 10" to the title.
Both songs are satirical talking blues, and both seem to be having fun with the same general ideas.
Early in his career, Dylan's political songs made him a celebrity among progressive intellectuals. By the time he recorded "I Shall Be Free No. 10," he'd started looking to separate himself from the scene. He made this clear in conversation with his romantic partner and friend Joan Baez, but he also discusses it in his songs and in his communication with the press. One high-profile public incident summed up his thinking at the time.
In December 1963, a few months before recording the song, the Emergency Civil Liberties Committee gave Dylan the Tom Paine Award (Paine was part of the American Revolution and an influential political thinker).
Dylan got very intoxicated at the awards ceremony, and in his acceptance speech he insulted the audience with a long screed where he told them: "First of all because they're young and it took me a long time to get young and now I consider myself young. And I'm proud of it. I'm proud that I'm young. And I only wish that all you people who are sitting out here tonight weren't here, and I could see all kinds of faces with hair on their heads - and everything like that, everything leading to youngness, celebrating the anniversary when we used overthrow of the House Un-American Activities just yesterday - because you people should be at the beach."
He closed by saying, "There's no black and white, left and right to me anymore. There's only up and down and down is very close to the ground. And I'm trying to go up without thinking about anything trivial such as politics."