An Achingly Beautiful Dialogue of Farewell and Lingering Hope
“Boots of Spanish Leather” by Nanci Griffith—though, of course, the original pen belongs to Bob Dylan—is a stark, poetic chronicle of two lovers grappling with an inevitable, devastating separation. It is less a song and more an epistolary exchange, a final, heartbreaking conversation where one is sailing toward a grand, unknown future and the other is anchored in a solitary, dwindling present. The song masterfully captures the complex, messy emotions of a love that ends not with a bang, but with a slow, agonizing drift apart, all channeled through the crystalline, emotive voice of Nanci Griffith.
The song’s profound emotional resonance is rooted in its origin: it was written by Bob Dylan in 1963 and released on his 1964 album, The Times They Are a-Changin’. While Dylan’s version remains the definitive original, a raw, fingerpicked acoustic ballad, Nanci Griffith’s rendition, released nearly thirty years later, on her 1993 album, Other Voices, Other Rooms, carved its own indelible mark. This album, a brilliant collection of covers that paid homage to the folk tradition that shaped her, became a signature moment in Griffith’s career, earning her a Grammy Award for Best Contemporary Folk Album.
Significantly, Griffith’s take on “Boots of Spanish Leather” did not chart as a single in the major US or UK pop charts, as it was a deeply respected cover on a folk-focused album. Yet, its enduring popularity among folk and Americana enthusiasts solidifies its standing as one of the most treasured interpretations of the Dylan classic. The story behind the original song is frequently linked to Dylan’s former girlfriend, Suze Rotolo, who went to Italy in 1962 to study art, creating a painful, protracted distance that served as the emotional foundation for the lyrics. The song, structured as a dialogue, features the woman leaving—”I’m sailin’ away, my own true love, I’m sailin’ away in the mornin’”—offering to send a token gift from her travels (“silver,” “gold,” or “diamonds”). The lover left behind repeatedly rejects the material offerings, pleading only for her swift return: “Oh, how can, how can you ask me again? It only brings me sorrow.”
But the heart of the song, the moment that delivers the emotional blow that resonates so powerfully with older listeners who understand the quiet finality of goodbye, arrives in the last three verses. A letter comes from the woman, and the dialogue collapses into a monologue of raw, realized pain. She writes, “I don’t know when I’ll be comin’ back again / It depends on how I’m a-feelin’,” a gentle but crushing admission that the separation is permanent.
The lover’s final response is the song’s piercing denouement. The one who wanted nothing now asks for “Spanish boots of Spanish leather.” It’s an act of capitulation, a final, bitter acceptance that what he truly desired—her return—is impossible. The boots, high-quality, long-lasting Spanish leather, are a material substitute for an irreparable loss. They symbolize his own need to walk away, to move on, to acquire “boots” for his journey that is now separate from hers. Nanci Griffith’s plaintive, pure voice delivers this final request with a delicate mix of sorrow and sudden, practical resolve, transforming Dylan’s lyric into a tender, nostalgic farewell for a generation who learned that even the deepest love can’t stop the western wind from calling a loved one away.