What happens when “The Times They Are A-Changin’” meets a world where nothing changes at all? In this episode of Hitchhiking Highway 61, we leave behind Bob Dylan’s anthem of progress and step into the bleak, haunting story of “Ballad of Hollis Brown.”Dylan paints the picture of a desperate farmer on the edge of survival — and forces us to wrestle with timeless questions: poverty, despair, choice, and the cycles of history that never seem to end. Is Hollis a victim? A villain? Both? And what does his story reveal about the struggles we still face today?Join us as host Kevin Fallon explores Dylan’s storytelling, the relentless rhythm of the song, and the uncomfortable empathy it creates. Along the way, we’ll reflect on why Dylan’s music still matters, why “nothing new under the sun” feels truer than ever, and what it means to notice the Hollis Browns around us before it’s too late.
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The Times They Are A-Changin'
On November 22, 1963, President John F. Kennedy was assassinated in Dallas, marking a cultural turning point that shattered America’s postwar optimism and ushered in the turbulence of the 1960s. In this episode of Hitchhiking Highway 61, host Kevin Fallon explores Bob Dylan’s The Times They Are A-Changin’ — an anthem written before Kennedy’s death but one that eerily captured the nation’s shifting mood. From civil rights to Vietnam to the rise of counterculture, Dylan’s stark folk declaration became the soundtrack to a decade in motion.
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I Shall Be Free
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.
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Talkin' World War III Blues
We live in wild times—and Bob Dylan knew something about that even back in 1963. In this episode of Hitchhiking Highway 61, we explore Dylan’s surreal, funny, and eerily relevant “Talkin’ World War III Blues,” a song that turns Cold War anxiety into a dreamlike satire. What does it mean to live through chaos? What do we do with fear, loneliness, and the sense that the world’s coming apart? From bunkers to Cadillacs, Dylan wanders through the wreckage looking not just for survival—but for connection. If you’ve ever felt like the last person left in a crazy world, this one’s for you.
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Oxford Town
In this episode of Hitchhiking Highway 61, host Kevin Fallon explores Bob Dylan’s hauntingly restrained protest song “Oxford Town,” written in response to the 1962 Ole Miss riots. Kevin unpacks the historical context behind the song—from the Jim Crow era to the violent backlash James Meredith faced when integrating the University of Mississippi—and reflects on how Dylan captured the quiet complicity of bystanders through deceptively simple lyrics. Drawing connections to the broader civil rights movement, including insights from Dr. Martin Luther King Jr., this episode reminds us how far we’ve come—and what it took to get here.
About Hitchhiking Highway 61: A Bob Dylan Inspired Podcast
Hitchhiking Highway 61 is a personal journey through the songs of Bob Dylan—one track at a time. Each episode dives into a Dylan song, exploring its lyrics, themes, and impact while weaving in personal stories and reflections.
Listen to Hitchhiking Highway 61: A Bob Dylan Inspired Podcast, Music, Money & Mayhem and many other podcasts from around the world with the radio.net app
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