Boots of Spanish Leather

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 to Dylan’s relationship with Suze Rotolo, “Boots of Spanish Leather” unfolds as a conversation between two lovers growing emotionally—and physically—apart. Kevin dives into Dylan’s emotional delivery, the song’s alternating narrators, and how unspoken truths can say more than words ever could. From the “lonesome ocean” to the symbolic final request for Spanish boots, the song becomes a meditation on exhaustion, denial, and learning to let go and move on.

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Jaksot(24)

All I Really Want To Do

All I Really Want To Do

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 lo...

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Restless Farewell

Restless Farewell

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 b...

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The Lonesome Death of Hattie Carroll

The Lonesome Death of Hattie Carroll

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...

2 Huhti 23min

When The Ship Comes In

When The Ship Comes In

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 F...

7 Maalis 13min

Only A Pawn In Their Game

Only A Pawn In Their Game

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 E...

22 Tammi 15min

North Country Blues

North Country Blues

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. Fro...

16 Joulu 202518min

One Too Many Mornings

One Too Many Mornings

On this episode of Hitchhiking Highway 61, Kevin Fallon explores Bob Dylan’sOne Too Many Mornings from The Times They Are A-Changin’. Dive into Dylan’s imagery of distance, choices, and reflection as ...

24 Marras 202513min

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