In I Shall Be Free, the last song on The Freewheelin' Bob Dylan, Dylan embraces the chaos-becoming both the hero and the joker, unmasking himself as he trades his serious folk image for surrealist absurdity, sharp satire, and wild humor. From relationships and race to politics, pop culture, and Cold War paranoia, Dylan takes a scattershot ride through the early '60s, unmasking the absurdity beneath it all. In this episode of Hitchhiking Highway 61, Kevin Fallon dives into Dylan's jester side, exploring how I Shall Be Free blends folk tradition with playful madness- and why sometimes, the only way to face a ridiculous would is to laugh right back at it.