“A Hard Rain’s A-Gonna Fall” is melancholy rather than angry. It’s frequently referenced that Dylan penned the song in response to the Cuban Missile Crisis, when in fact he had written and performed the song a month before the event occurred. The song features some of Dylan’s best and most complex songwriting not only to that point, but also across his entire career. He weaves surreal and striking images like something out of a Game of Thrones dream sequence, each symbolizing the sorrow and horror of war. Dylan famously said, “Every line in it is actually the start of a whole new song. But when I wrote it, I thought I wouldn’t have enough time alive to write all those songs, so I put all I could into this one."

With “Talking World War II Blues,” Dylan humorously improvises his view of what life would be like after the bomb drops. Dylan describes an increasingly absurdist view of life in New York City after nuclear destruction. Dylan “dreams” of wandering the mostly deserted streets, shunned or shot at by the few survivors he encounters, eventually seeking the solace of a recorded voice of an operator telling him the time as a substitute for human interaction. The dark wit belies the fear of loneliness and abandonment that would go along with being the sole survivor of a nuclear holocaust, while Dylan dispenses a little wisdom along the way. His most profound revelation? A Cadillac’s not a bad car to drive after a war.

Abandonment is a central theme throughout Freewheelin’, though often associated with heartbreak. “Girl From the North Country” features Dylan playing a simple guitar melody, singing about his lost true love from where “the rivers freeze and summer ends.” The song was influenced by Dylan’s first trip to England, specifically his immersion into the London folk music scene and his contact with many of its gifted singers. Dylan later re-recorded the song as a duet with Johnny Cash as the lead song for the country-tinged Nashville Skyline (1969). While it’s great to hear two masters collaborate and breathe new life into a great song, I’ve always preferred the original version.