Bob Dylan has written over 600 hundred songs in a career that has spanned sixty years and earned him, among other honors, a Nobel Prize for Literature. Many consider him the greatest American songwriter of the rock and roll era. Others consider him overrated and pretentious.
I lean more toward the former, but I do admit that when you write 600 songs, some of them may tilt toward pretentious. But do the math with me: even if we allow that – oh, I don’t know, let’s say that 100 of his songs suck, that still leaves 500 good-to-great ones floating around out there.
Today, we’re going to choose five of the best. It may not seem that the world needs another “Dylan’s best songs” list and if any of the dozens of similar lists I have read over the years actually got it right, I wouldn’t feel the need to do this. Sadly, none have, and so it falls to me.
Five best Bob Dylan story songs ever
But I’m doing this a little differently. Bob Dylan has written songs in many styles and on many topics, but I think I can split them up into four rough categories: Story songs, political songs, love songs, and personal songs. That last category is admittedly a catchall for all the songs that don’t conveniently slot into one of the first three. My eventual goal is twenty songs, so I will pick five from each category. Today’s winner is story songs.
Of course, there is some overlap. One of his most famous story songs, “Hurricane,” from 1976’s Desire is both a great story song and a great political song. Spoiler alert: it is not on today's story song list. You’ll just have to tune in next time to see if makes the political countdown. The point is – some songs could be placed on two, or more, of these lists.
So onto the stories…
On his self-titled debut album, the greatest American songwriter only wrote two original songs. Bob Dylan was mostly composed of traditional folk and blues tunes that were popular amongst the burgeoning Greenwich Village folk scene in the early ‘60s. One of those original compositions was “Talkin’ New York,” a talking blues song about the young singer’s introduction to the Big Apple. Dylan has been writing story songs ever since. Here are his five best.
“Desolation Row” (1965)
Dylan closes out Highway 61 Revisited with an eleven-minute acoustic story filled with a panoply of intriguing characters. It has a vaguely Western feel about a downtrodden, corrupt society that is being passively observed by the singer and his lady.
On an album famous for the singer’s newfound love of electric guitars, this distinctly non-electric tune has a particular poignance. The song benefits enormously from Nashville guitarist Charlie McCoy’s largely improvised, flamenco-styled guitar flourishes.
”Isis” (1976)
“Hurricane,” about the incarceration of boxer Rubin Carter, opens Desire. The song that follows it, a story about love, greed, and failed dreams, is even better.
With minimal orchestration – just piano, bass, drums, harmonica, and Scarlett Rivera’s violin insinuating its way through the entire tale – Dylan writes some of his best lyrics – including one of my favorite verses – “The wind, it was howlin’ and the snow was outrageous – We chopped through the night and chopped through the dawn – When he died, I was hopin’ that it wasn’t contagious – But I made up my mind that I had to go on.”
“Black Diamond Bay” (1976)
In addition to “Hurricane” and “Isis,” Desire also has “Joey,” about the life and death of gangster Joey Gallo. But my favorite story on an album filled with great tales is this underrated gem about a volcano that wiped out an entire unnamed island. Like most of the tracks on the album, Dylan co-wrote this one with theatre director Jacques Levy, and Levy’s influence can be seen in sharp visualization of the unfolding drama.
And as in “Isis,” Scarlett Rivera’s violin provides a thread that binds the story together. Dylan tells remarkably detailed stories about a Grand Hotel’s-worth of disparate characters before closing with an amazingly sharp and cynical verse about how so many human tragedies seem to come and go in the blink of an eye.
“Tweeter and the Monkey Man” (1988)
This is the only song on my list that was not included on one of Dylan’s 40 solo albums. This came from his collaboration with the Traveling Wilburys. Though George Harrison provides most of the guitar, and Harrison, Tom Petty, and Jeff Lynne contribute backing vocals on the earworm chorus, this is all Dylan.
An epic story of love and crime in five and a half minutes, it is about an outlaw hero and a frustrated housewife, and as such, can be seen as a spiritual successor to one of my favorite Dylan stories (that did not quite make this list) “Lily, Rosemary and the Jack of Hearts.” But this is more of a down-and-dirty swamp rock song and contains a surprisingly offhand reference to a transgender character.
"Murder Most Foul" (2020)
As Dallas, 1963 fades further into history, the Kennedy assassination will enter a new phase. Firsthand accounts will dwindle and it will become history, divorced from current events by time memory. Dylan was not there to see John Kennedy assassinated, but like the rest of the country, he was old enough to be wounded.
His epic account of that day may be the last time someone who was old enough to remember the event may write about its impact. If so, "Murder Most Foul" provides a potent summation of an assassination that has never stopped rippling through American consciousness.
It's 17 minutes of memory backed by a mournful cello, a violin, and several blended keyboards. Drums and the occasional cymbal crash creep along in the distance. Dylan's voice also comes from memory, recalling all manner of pop culture from the era - references that continually butt up against the brutality of cold-blooded murder.
In the middle of it all, Dylan offers his clearest statement: "The day they killed him someone said to me, 'Son -- The day of the antichrist has just only begun." "Murder Most Foul" is about the Kennedy assassination, but it is about far more than that. It is about the demise of America. It positions the killing at the forefront of a long, dwindling cycle of the snuffing out of hope whenever it dares raise its head. It is a hypnotic tale, fitting for the end of the era, fittingly told by a Nobel laureate.
Honorable mentions: “The Ballad of Frankie Lee and Judas Priest," "Lily, Rosemary, and the Jack of Hearts,” and “Hurricane.”