Considering that he’s been churning songs out for more than 60 years, it’s not surprising that Bob Dylan has written on just about every topic there is. Like all songwriters, however, Dylan has often gravitated to tales of lost love and broken hearts.
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We looked back through Bob’s catalog to find four heartbreak songs of note. Some you might know, some might seem off the beaten path, but all are downright devastating.
“Boots Of Spanish Leather”
What Dylan pulled off with this song might rank as one of his most underrated songwriting achievements. Even if you don’t know exactly what’s happening and who’s saying what to whom, “Boots Of Spanish Leather” is quite affecting. There’s something about that plaintive acoustic guitar and Dylan’s lonesome delivery that sells it immediately. But then when you delve into the structure, you start to appreciate it more. About half the song is a back and forth of letters between two lovers, one far away from the other. The rest finds the narrator telling the story solo, explaining that he received one missive that signaled the end of the relationship. When you look back at her previous words, the hints were there.
“I Threw It All Away”
Throughout his career, Bob Dylan has periodically sent shock waves through the music world with utterly surprising shifts in artistic direction. Nashville Skyline stands out as one of the most memorable of these sudden turns. It came during a period when he wasn’t touring and was mostly free from the white-hot spotlight that accompanied him in the mid-60s. Looking to shrug off expectations, he released an album of straightforward country songs in the vein of Hank Williams. But Dylan couldn’t completely shroud his brilliance in simplicity. “I Threw It All Away” hits as hard as any of his wordy songs because every note and syllable counts. The bleak titular admission sets the regretful tone of this gem.
“Tangled Up In Blue”
On Blood On The Tracks, Dylan wrote with revelatory depth. He eschewed simple narratives in favor of a painterly approach. As such, he attacked verses as if separate sections of the canvas, able to stand on their own but also part of the whole. That makes songs like “Tangled Up In Blue” a bit difficult to follow when you try to go along with all the narrator’s experiences and whereabouts. But at the core of it all is the deep sorrow he feels at having lost the love of his life somewhere along the line. The narrator may let us know about his escapades amidst national revolutions and strip clubs. Ultimately, those events are mere distractions from the ever-present memories of his ex, to whom he swears he’ll return somehow.
“This Dream Of You”
On the 2009 album Together Through Life, Bob Dylan ceded some lyrical duties to Robert Hunter, known for his work with the Grateful Dead. “This Dream Of You” marks the only song on the album completely penned by Bob. He made that lone solo ride. The song drifts about on a light-footed, vaguely Latin rhythm. But there’s nothing at all light about what the narrator is enduring. Every moment of his life is colored by his obsession with the person whose absence haunts him. Not even a falling star can redeem him in the final verse. “All I have and all I know,” he sings. “Is this dream of you that keeps me living on.” But what kind of life will it be if that dream never comes true?
Photo by Alice Ochs/Michael Ochs Archives/Getty Images
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