5 Heartbreakingly Great Love-Gone-Wrong Songs by Bob Dylan

Bob Dylan‘s songs often contain “multitudes,” to use a Walt Whitman phrase Dylan borrowed for a recent track. Occasionally, he narrows his focus down to a single topic. And when that topic is love gone wrong, well, the songwriting results he delivers are often staggering.

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These five songs show Dylan digging deep into the pain and suffering of relationship friction with revelatory results. We could have gone a hundred deep with this list and still left some great Dylan weepers out of the mix. But these five, listed in chronological order, are on another level.

“Boots of Spanish Leather”

The degree of difficulty in this song alone makes it a worthy addition to this list. It takes the form of a series of letters between a guy and his girl, who is currently on a different continent. As they go back and forth, she presses him on what exactly he’d like her to bring back for him, almost as if she’s trying to steer the conversation away from sentiment. Suddenly, the letters are gone, and it’s just him moaning about the fact that her last letter told him they were through. He finally decides to ask her to bring back the titular footwear, small consolation now that he’s lost everything else.

“One of Us Must Know” (Sooner or Later)”

We often focus on the lyrics of Dylan songs, and understandably so. But his best stuff also provides a musical jolt. This track from his legendary Blonde on Blonde album veers from quiet, atmospheric verses, with Al Kooper’s organ moaning like a distant ghost, to thrillingly urgent refrains, when pianist Paul Griffin charges through the arrangement like an elegant steed. The song relates how communication issues can lead to relationship breakdowns, with evocative imagery like blinding snow drifts rendering the heartbreak tangible and harrowing.

“I Threw It All Away”

Dylan stripped down his vocal gymnastics to fit his words into traditional country-song structures on the 1969 album Nashville Skyline. That might have given the uptempo songs a bit of an odd feel compared to other songs of his. But the technique works wonders on this ballad. Hank Williams himself would have been hard-pressed to come up with something as concise and devastating as this one. Give credit to the melody, including the liltingly sad guitar hook that travels through the song, and to Dylan locating boundless depths of regret via the simplest possible terms.

“Idiot Wind”

His protestations about the album’s meaning to the contrary, it’s hard to deny Dylan was exploring his marriage’s slow disintegration in the songs on Blood on the Tracks. You can pull any one of several songs from that album and find some serious relationship agita. But “Idiot Wind” is the one that pushes that stuff up to 11. Dylan being Dylan, he adds some misdirection to make us half-believe the press is the target of his ire. But no newspaperman or magazine scribe could ever engender the hurt and disappointment evident in his nearly off-the-rails vocals. Bonus points for the twist at the end, where he admits his own fault in the fallout.

“Most of the Time”

Dylan locked on to a clever hook phrase with “Most of the Time.” It allows him to both admit and deny how bad this woman’s departure is for him. And it’s accurate, because anyone who has endured a breakup can tell you how wide stretches of seeming normalcy can be interrupted by sudden whirlwinds of sorrow. The production of Daniel Lanois (even though Dylan would likely be loath to admit it) works wonders here, as it emits that atmosphere that seems like Dylan is the only person on a barren planet while he’s singing, which is how being left behind by a romantic partner can often feel.

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