Five fantastic and ridiculously underrated Bob Dylan love songs

The best Dylan tracks about the greatest emotion.
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A Bob Dylan love song is not generally the stuff of teeny-bopper dreams. Not a lot “arms/charms” rhymes, or looking forward to a radiant future. It’s true that the best love songs possess the DNA of heartbreak, even if they are upbeat numbers. Brian Wilson could sing “Wouldn’t It Be Nice,” and Tom Petty could lament “The Waiting,” even though they knew the best was yet to come. It was that sense of longing that could one day be fulfilled that infused what might otherwise be a sappy ballad into something far more profound.

But Dylan, when he chose to write about love, usually looked at it from the other side. In the aftermath, he looked at what might have been, or at what was once, but is no more. Nowhere was this more obvious than on one of his greatest albums – Blood On the Tracks – written during the breakup of his marriage to Sara Lownds. If I so desired, I could populate this entire list with mournful songs of lost love from that single album.

But Dylan was capable of reveling in all the flavors of love – not merely the heartbreak. So this list of his five greatest love songs will span the gamut, from regretful to playful, and anything that falls in between.

Here are Bob Dylan’s five greatest love songs


Dylan’s self-titled debut album in 1962 was mostly covers. He began changing the course of modern music with his follow-up, 1963’s The Freewheelin’ Bob Dylan. These are his own songs, opening with the era-defining “Blowin’ in the Wind,” along with the coffee-house sensation “A Hard Rain’s A-Gonna Fall.”

And then there was this simple, four-verse acoustic guitar and harmonica break-up song that began with the fateful “Well, it ain’t no use to sit and wonder why, babe….” And got more world-weary and passive-aggressive from that point on. It is truly one of the best FU kiss-offs, made all the better for just how offhand it all appears.

The 22-year-old Dylan is at his most acerbic in taking down the woman he once loved, “a child, I am told,” who “just kind of wasted my precious time.” Much of what we would come to love about early Dylan is on display – the simple but effective melody, the wordplay and wit, and the wailing harmonica. It’s a bitter song, but there is a tender sadness at what might have been which raises it above the merely angry to a level of sublimity.

Just take a quick peek at the varied artists who have covered it over the years – from pure folkies Joan Baez and Peter, Paul and Mary to the weathered outlaw heroes Waylon Jennings and Johnny Cash. Susan Tedeschi did a blues version, on her own, or backed by the slinking slide of the Allman Brothers. Duane Eddy applied his surf guitar to the tune, the Nitty Gritty Dirt Band did it in earnest bluegrass, and Glen Campbell did the most countrified version, with Randy Travis running a close second.

Melanie and Kesha slowed it to a crawl to accommodate their spacy vocals, while a very young Cher shouted it for all she was worth just a few years after Dylan’s original. Oh yeah, and some guy named Elvis put his own spin on it too. It's a pretty good song.