Hitchhiking Highway 61: A Bob Dylan Inspired Podcast

In this episode of Hitchhiking Highway 61, host Kevin Fallon looks at the first song on Another Side of Bob Dylan, All I Really Want To Do. The song marks a turning point for Dylan as the singer is looking to break free of exceptions and create on his own terms.

In this episode of Hitchhiking Highway 61 we explore Restless Farewell by Bob Dylan, where he says goodbye to his folk era on The Times They Are A-Changin'. The song touches on fame, identity, media backlash, and the need to move forward. Blending music analysis with personal stories, it's about change, letting go, and stepping into the unknown.

In this episode of Hitchhiking Highway 61, we explore The Lonesome Death of Hattie Carroll and how it reflects the tension between hope and injustice in 1960s America. After performing at the March on Washington, Bob Dylan was inspired by the real-life killing of Hattie Carroll. We break down the song's storytelling, its critique of systemic injustice, and how it differs from Dylan's prote...

In this episode of  Hitchhiking Highway 61 , we explore  “When the Ship Comes In”  from The Times They Are a-Changin' by Bob Dylan. First performed with Joan Baez at the March on Washington for Jobs and Freedom in 1963, the song sounds like a sweeping civil-rights anthem—but it was actually inspired by Dylan being denied a hotel room because of his appearance. We unpack how Dylan turned a pett...

In this episode of  Hitchhiking Highway 61 , host Kevin Fallon explores Bob Dylan’s haunting ballad  “Boots of Spanish Leather”  from  The Times They Are A-Changin’ , weaving together lyrical analysis, music history, and a deeply personal story about childhood solitude, family distance, and the and the subtle ways we replace genuine feeling with safer stand-ins. Recorded in 1963 and often linked t...

In this episode of  Hitchhiking Highway 61 , host Kevin Fallon examines Bob Dylan’s 1964 protest song “Only a Pawn in Their Game” from  The Times They Are A-Changin’ , written in the aftermath of Medgar Evers’s assassination. His murder—and the decades-long fight for justice that followed—would echo through American history and into the music of Dylan. Rather than focusing solely on the man who pu...

In this episode of Hitchhiking Highway 61 , we take a deep dive into Bob Dylan’s “North Country Blues,” a haunting narrative about life in a failing mining town and the quiet weight of staying put. From its roots in Woody Guthrie–style folk storytelling to its echoes in later songs by artists like Bruce Springsteen and Pearl Jam, “North Country Blues” explores working-class struggle, economic decl...

On this episode of  Hitchhiking Highway 61 , Kevin Fallon explores Bob Dylan’s One Too Many Mornings  from The Times They Are A-Changin’ . Dive into Dylan’s imagery of distance, choices, and reflection as he captures the bittersweet pain of love and missed opportunities. This episode highlights the song’s themes of perspective, crossroads, and the ripple effects of small “what if” moments.

Join host Kevin Fallon on Hitchhiking Highway 61 as he dives into Bob Dylan's 1964 classic With God On Our Side. In this episode we explore Dylan's take on history, morality, and the heavy intersection of religion and war. We examine how Dylan questions whether any country, or person, can truly claim God is on their side. Along the way, he shares his own perspective as a history teacher an...

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, choi...

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 shif...

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 beneat...

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...

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 compli...

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 ro...

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 sometim...

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 D...

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...

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, refle...

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 carefull...