Hitchhiking Highway 61: A Bob Dylan Inspired Podcast

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.

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.

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.

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.

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.

In this episode of Hitchhiking Highway 61, we dive into Bob Dylan's Dream, one of Dylan's most nostalgic songs. It's a heartfelt look back at old friends, simpler times, and the bittersweet ache of growing up.Host Kevin Fallon uses the song to reflect on youthful memories-from skating through a high school at night to playing impromptu metal shows and launching cars off abandoned roads. He also compares Dylan's melancholy with the optimism of Willy Nelson's On the Road Again and explores what these two roads say about how we face the passage of time. All that and a little Pantera.

In this episode, we dive into Don't Think Twice, It's All Right, one of Bob Dylan's most iconic breakup songs- and one of his most emotionally complex. Is it a calm farewell or a bitter self-defense? Along the way, I draw parallels to The Catcher in the Rye, unpack Dylan's own words about the song, and reflect on how emotional distance, sarcasm, and silence can shape, and sometimes sabotage, our relationships. From punk covers (shout out to Mike Ness of Social Distortion) to personal stories, this one hits close to home.

In this episode of Hitchhiking Highway 61 we're diving into Bob Dylan's haunting anthem "A Hard Rain's A-Gonna Fall," a song that echoes with Cold War dread, nuclear shadows, and apocalyptic visions. This episode unpacks: the song's roots in Cold War fears, its unexpected connection to Godzilla, Dylan's place in apocalyptic media, and how it inspired artist from The Doors to Iron Maiden. It's a wild ride through poetry, paranoia, and pop culture-don't miss it.

In this episode of Hitchhiking Highway 61, Kevin Fallon explores how Bob Dylan's Blues echoes the restless spirit of Jack Kerouac's On the Road. Set against the backdrop of postwar conformity, the episode traces a thread of rebellion and disillusionment through generations- from beat poets to punk bands like Minor Threat and grunge icons like Nirvana- all in search of something real.

In this episode host Kevin Fallon uses the classic novel On the Road by Jack Kerouac as a lens to explore the themes of longing, connection, and the search for meaning in the Bob Dylan song Down the Highway. He'll also make a few personal connections and tell stories- and lessons learned- of his own cross-country road trip.

In this episode, host Kevin Fallon looks at the Bob Dylan classic, Masters of War,inspired by a warning from President Eisenhower to the nation of the military industrial complex. Kevin looks back in American history to see how profit motives have affected war and those involves and also recounts his own father's experience in Vietnam.

In this episode of Hitchhiking Highway 61, host Kevin Fallon dives into Bob Dylan's "Girl from the North Country." The song originally appeared on Freewheelin' Bob Dylan and later revisited as a duet with Johnny Cash. Fallon examines the themes of love, memories, regret, and the choices that shape our lives.

In this episode of Hitchhiking Highway 61, host Kevin Fallon dives into Bob Dylan's iconic Blowin' in the Wind, exploring how its series of powerful, unanswered questions make the song more about the journey of self-reflection than finding concrete answers. Kevin reflects on the broad social and political struggles of the 1960s while also reflecting on his own road of growth though moments of hardship and resilience.

In this episode, we delve into Bob Dylan's "Song to Woody," a tribute to his musical mentor, Woody Guthrie. Host Kevin Fallon explores how Guthrie's influence shaped Dylan's music, and how this song represents both a homage and pivotal moment in Dylan's own emergence as a voice for social change. He also draws from his own experiences in the underground music scene, reflecting on the sense of belonging that connects his journey to Dylan's.

In this debut episode of Hitchhiking Highway 61, Kevin Fallon begins his personal journey though Bob Dylan's music with "Talkin' New York," Dylan’s first song to introduce himself to the world.  The song paints the picture of young Dylan arriving in New York City with nothing but a guitar and big dreams. But it's more than just an arrival story-its the start of a legend, a myth that Dylan carefully crafted around himself from the beginning.  Kevin also connects the song on a personal level, sharing how is own experiences and dreams, led him to Dylan's music.