Some songs have been overshadowed by zeitgeist-shaping greatness and others buried on a clunker of an album, but all have been right there for the appreciating.
It’s time for another Bob Dylan list. That means it’s also time to line up the disclaimers like tequila shots at a cantina in Durango. First of all, “overlooked” is a relative term. After a career in the spotlight spanning seven decades, even the most obscure Dylan songs have long been dusted off, dissected to death, and turned into social media handles. And I’ll turn in my badge and bury my guns in the ground before I make the deadly mistake of calling any of these songs “underrated” or “forgotten.” Mama didn’t raise no fool. I’ve butted heads before with handles like Duncanandbrady1992 and desire no part of their keyboard wrath.
That said, the conceit behind this list wasn’t to flex or kick grains of sand in anyone’s face. That’ll come a bit later in the summer when we’ll deep-dive into Dylan’s Bootleg Series and geek out over alternative takes of outtakes. No, this list is about the songs we’ve listened to, or even skipped, 100 times before something finally clicked. The ones that nobody ever really seems to talk about much. All are Dylan originals from studio albums that have been widely available for, in many cases, decades. In other words, to paraphrase Dewey Finn: “No secret songs.” Some have been overshadowed by zeitgeist-shaping greatness and others buried on a clunker of an album, but all have been right there for the appreciating.
If slogging through Dylan’s discography over the past few weeks has taught me anything, it’s that our relationships with his songs are like, well, a relationship. These are songs you fall in and out of love with, crush on, sour on, rekindle with, and continue to see in a different light as the years pass. They change as we do. They are songs you know by heart one year and songs that act like you’ve never met the next time you bump into them. In some ways, that’s the beautiful gift that Dylan has given us. As was the case for me with several of these songs, you can still hear something different on that 101st listen. In that moment, everything feels new all over again. And, in that way, it keeps his music, and maybe even us, forever young.
“Bob Dylan’s Dream” (The Freewheelin’ Bob Dylan, 1963)
It’s not hard to lose track of this quiet recollection of a sad dream upon a train. Freewheelin’… boasts many of Dylan’s most beloved compositions and songs that truly marked the social headiness of the 1960s: the generation-defining anthem “Blowin’ in the Wind,” the scathing polemic “Masters of War,” and the portentous forecast “A Hard Rain’s a-Gonna Fall” among so many others. But that’s no reason to sleep on “Bob Dylan’s Dream.” Borrowing both melody and sentiment from traditional broadside ballad “Lord Franklin,” a young Dylan fondly remembers the joyful camaraderie of bygone days over clicking strums. It’s an early example of Dylan’s ability to capture emotional nuance in the simplest language, the song taking a crestfallen tone as he comes to understand that such carefree days were always numbered. If “My Back Pages” would later take a poke at the assured fervency of youth, then “Bob Dylan’s Dream” acknowledges that those same fleeting days are among the simplest and most enviable of our lives.
Definitive Dylan: “And our choices there was few / So the thought never hit / That the one road we travelled, we’d ever shatter or split”
“Bob Dylan’s 115th Dream” (Bringing It All Back Home, 1965)
No, not all the songs on this list are plucked from the Land of Nod. That said, this arbitrarily numbered fantasy closes out the electric side of Bringing It All Back Home, largely considered Dylan’s Dear John letter to the folk scene. In a souped-up take on the melody of “Motorpsycho Nitemare” from Another Side of Bob Dylan, the song’s protagonist, a sailor in the employ of Captain Arab (read: Ahab), reimagines America’s founding in farcical fashion. It’s a raucous, cartoonish romp full of comical hijinks, punny playfulness, and ribald humor. More importantly, it demonstrates that Dylan had lost none of his gift for language or command as a singer as a result of plugging in. Perhaps, the song’s acoustic false start, which sent producer Tom Wilson into a laughing fit, might best be characterized as Dylan’s technicolor first steps into Oz as listeners realize that we’re not in Kansas, or even Greenwich Village, anymore. While it may get overshadowed by tambourine men, Maggie’s ma, and Johnny in the basement, “Bob Dylan’s 115th Dream” remains a lampoonish, harpoon-brandishing classic.
Definitive Dylan: “Well, the last I heard of Arab / He was stuck on a whale / That was married to the deputy sheriff of the jail”
“Down Along the Cove” (John Wesley Harding, 1967)
Though Dylan had no interest in making any kind of splash at the time, John Wesley Harding has grown into one of the songwriter’s most celebrated albums. However, that’s not to say that Dylan intended for these short, fragmented parables, including the apocalyptic “All Along the Watchtower,” to end up as stripped down and musically sparse as we know them. After Band members Robbie Robertson and Garth Hudson declined to add dubs to Dylan’s basic tracks, producer Bob Johnston suggested that pedal steel guitarist Pete Drake join Dylan (on piano here) and combo members Kenneth Buttrey (drums) and Charlie McCoy (bass) on a couple of tracks, including “Down Along the Cove.” Tucked near the back of JWH, this swinging, little country blues number finds an elated Dylan playing lookout for his girl as the band absolutely cooks. The song, along with album closer “I’ll Be Your Baby Tonight,” hints at not only other directions John Wesley Harding could’ve gone, for better or worse, but also teases what was to come a couple years later on 1969’s Nashville Skyline.
Definitive Dylan: “Down along the cove / We walked together hand in hand / Ev’rybody watchin’ us a’go by / Knows we’re in love, yes, and they understand”
“Tell Me That It Isn’t True” (Nashville Skyline, 1969)
There’s a great line in 2024’s Bob Dylan biopic, A Complete Unknown, where Timothée Chalamet’s exasperated Dylan tells future collaborator Bob Neuwirth that he wants to be “whatever it is they don’t want me to be.” It’s a line that could reflect most any era of Dylan’s career, including his full-on departure into country rock on Nashville Skyline. As the political tumult of the late ‘60s heated up, Dylan opted out and instead released a collection of straight-forward, Nashville-flavored tunes that couldn’t possibly be interpreted as anything but simple love songs. Adopting an unrecognizable country croon, often attributed to a break from smoking, Dylan smoothly belted out a string of effortless, little rockers like “Tell Me That It Isn’t True.” The chart-topping “Lay, Lady, Lay” and Dylan’s duet with Johnny Cash on “Girl from the North Country” may garner more spins, but there’s such an irresistible appeal to the bouncing interplay between the band and Dylan’s croon on “Tell Me That It Isn’t True” as he crosses his fingers that the rumors about his girl’s wandering affections aren’t correct. Not only do we see here how easily Dylan could slip into other genres, but many, including Kris Kristofferson, credit Dylan’s string of Nashville recording sessions for making country cool again.
Definitive Dylan: “I have heard rumors all over town / They say that you’re planning to put me down / All I would like you to do / Is tell me that it isn’t true”
“Day of the Locusts” (New Morning, 1970)
Many championed New Morning as a return to form following the dumbfounding release of Self-Portrait earlier the same year. Part of that sentiment likely stemmed from Dylan having dropped the croon he had adapted for Nashville Skyline in favor of his more familiar nasal delivery. However, as a songwriter, the cobbled-together nature of this collection—a few songs of which had started as commissions for poet/playwright Archibald MacLeish—seemed to find Dylan seeking out new types of inspiration. The germ of “Day of the Locusts” came from Dylan dragging his feet to receive an honorary doctorate from Princeton, an event that happened to coincide with the Brood X emergence of cicadas across campus. Here, Dylan turns the details of the disturbing experience into an emphatic episode that ends with him and then-wife Sara driving off into the hills, thankful to have survived such a public appearance. At that time, it wasn’t the type of fare fans would’ve thought of as fodder for a Dylan song; however, everything from the opening field sounds and return to surrealist imagery to the conviction of Dylan’s singing and his band’s jubilant performance pulls the listener right in. As a songwriter, it feels like Dylan glancing back over one shoulder in order to figure out what lies ahead.
Definitive Dylan: “The man standin’ next to me, his head was exploding / Well, I was prayin’ the pieces wouldn’t fall on me”
“Something There Is About You” (Planet Waves, 1974)
You can’t tell the story of Bob Dylan without The Band and vice versa. Together, they brought Dylan’s electrified rebellion to the masses, inadvertently invented the rock bootleg, and waltzed together as collaborators for more than a decade right up until The Band’s initial split. Though Planet Waves boasts its fair share of championers, it’s hard not to feel like some of these songs ended up making ripples when they could’ve made waves. “Something There Is About You,” clunky syntax and all, finds Dylan and The Band falling into step like old times as the singer tries to figure out what it is about a new connection that stirs so many powerful emotions within. While nowhere near as realized as anything that would appear on Blood on the Tracks the following year, the way Dylan explores the snares of love, memory, and confusion certainly could be viewed as a spiritual predecessor of sorts to “Tangled Up in Blue.”
Definitive Dylan: “Thought I’d shaken the wonder and the phantoms of my youth / Rainy days on the Great Lakes / Walkin’ the hills of old Duluth”
“Black Diamond Bay” (Desire, 1976)
A Greek, a gambler, a soldier, and a lady in a necktie and Panama hat all check into a tropical resort for a vacation that none of them will ever come back from. Yes, that’s right. Bob Dylan and writing partner Jacques Levy basically wrote a deadlier version of The White Lotus way back in the mid-’70s. This Joseph Conrad-inspired hard-luck story (its moral: shit happens every day) about folks on holiday may seem tame on an album full of boxers, gangsters, and grave robbers, but it actually ends up being the wildest trip on Desire. This light and airy album version—stripped down from earlier takes — finds Dylan setting the scene for a tale of forbidden love, vice, and despair turned on its head by a natural disaster. Dylan and Levy’s cinematic lyrics bring the bustling, doomed resort to life, and Dylan’s masterful phrasing—accented by Scarlet Rivera’s violin and backing vocals from a young Emmylou Harris—make this easily one of the most enjoyable sing-alongs in his canon. Unlike those who went down with the island that day, listeners should want to go back to “Black Diamond Bay” time and time again.
Definitive Dylan: “Up on the white veranda / She wears a necktie and a Panama hat / Her passport shows a face / From another time and place / She looks nothin’ like that”
“True Love Tends to Forget” (Street-Legal, 1978)
A central motif across Bob Dylan’s career has been being out of step with his audience. Whether he’s forging ahead artistically, utterly disinterested, or just being stubborn, Dylan rarely has given fans what they think they want. In the case of an album like 1978’s Street-Legal, many critics and listeners almost took it as a slap in the face. After redefining the breakup album with Blood on the Tracks, finally giving The Basement Tapes an official release, and capturing the public’s imagination with the story-songs of Desire, Dylan dared to step back into the spotlight with a large pop-rock outfit and, gasp, lady backup singers. The shame of it all is that perfect pop songs like “True Love Tends to Forget” have never gotten the love they richly deserve. From the opening line (“I’m getting weary looking in my baby’s eyes”), Dylan sounds all in emotionally on this relationship that’s “like playin’ Russian roulette.” He’s still in great voice, and the pop guitars, tenor sax, and backing vocals on the chorus are the perfect complement. Again, we see Dylan step right into an adjacent genre and not miss a single brilliant beat.
Definitive Dylan: “I was lyin’ down in the reeds without any oxygen / I saw you in the wilderness among the men / Saw you drift into infinity and come back again / All you got to do is wait, and I’ll tell you when”
“Pressing On” (Saved, 1980)
Ironically, the same public that had once anointed Dylan their prophet had little interest in his plunge into his own faith. Say what you will about Saved and Dylan’s string of Christian albums, but it’s difficult to question the born-again artist’s sincerity, and, admittedly, Saved actually finds Dylan pulling in one direction—even if it’s not the direction most fans would’ve liked—rather than aimlessly wandering the musical desert as he did for most of the ‘80s. Much as he once adopted the language and cadences of the folk tradition, “Pressing On” finds Dylan ready to shake your stained-glass windows and rattle your pews as he enthusiastically testifies over building piano and gospel backing singers. It’s definitely one of his most passionate, forceful vocals of the era. He calls out the doubters and lets all listening know, as he has throughout his career, that he’s moving on, and there’s no turning back. It’s too much of a sermon for some tastes, too preachy, but damn if it doesn’t make you want to drag your ass back to church this Sunday and throw on a choir robe. Hallelujah!
Definitive Dylan: “Many try to stop me, shake me up in my mind / Say, ‘Prove to me that He is Lord, show me a sign’ / What kind of sign they need when it all come from within / When what’s lost has been found, what’s to come has already been?”
“The Groom’s Still Waiting at the Altar” (Shot of Love, 1981)
If you’ve attended Dylan shows in recent years, you probably know that “Every Grain of Sand” has become one of his go-to closing numbers. This final song off 1981’s Shot of Love not only closed the book on Dylan’s trio of evangelical records but, in many eyes, redeemed a period of his career that not many truly understood or appreciated. One of its too-often-neglected album-mates, “The Groom’s Still Waiting at the Altar,” didn’t even appear on the initial release of Shot of Love. It’s the only instance of Dylan going back and changing an album’s sequence after the fact. This rollicking blues romp—a first cousin to something like “Leopard-Skin Pill-Box Hat”—finds Dylan spitting lines like a preacher from a pulpit about a world that can’t possibly hold. It really doesn’t matter that we don’t know what it all adds up to; it’s one of Dylan’s most infectious jams ever. “Groom..” has since been included on several greatest hits compilations, but it’ll always be that badass Shot of Love song that inexplicably got rejected and then spent the next 45 years getting sand kicked in its face by the album’s beloved closer.
Definitive Dylan: “Cities on fire, phones out of order / They’re killing nuns and soldiers, there’s fighting on the border / What can I say about Claudette? / Ain’t seen her since January / She could be respectfully married or running a whorehouse in Buenos Aires”
“Don’t Fall Apart on Me Tonight” (Infidels, 1983)
I’ve never quite known how to read the fact that Dylan titled his return to secular music Infidels. Then you start listening to the record, and it begins to make more sense. For the most part, it’s an incredibly pessimistic, polemical, and political album that still largely draws from religious ideas and references. That makes album closer “Don’t Fall Apart on Me Tonight” a bit of an outlier but also welcome respite as a love song. Joined by Mark Knopfler (Dire Straits), Mick Taylor (The Rolling Stones), and the reggae rhythm section Sly & Robbie, Dylan begs his girl to hold it together because he’s struggling to, and Lord knows the world’s crumbling around them. Okay, so maybe it’s not the bubbly love song its pop sound might suggest, but it does feature some of Dylan’s most inventive language (imagining himself as a painting or considering a career change to medicine) and offers a glimmer of hope. After listening to Infidels, we’ll take it.
Definitive Dylan: “But it’s like I’m stuck inside a painting / That’s hanging in the Louvre / My throat starts to tickle, and my nose itches / But I know that I can’t move”
“I’ll Remember You” (Empire Burlesque, 1985)
Say what you will about Empire Burlesque, but Dylan really did try here. By his own admission, the same can’t be said about some other albums that rounded out the decade. So, we can forgive some of the trend chasing, painful ‘80s production, and even that sports jacket on the album cover. Also, and most importantly, despite all the panning of this record over the years, we can find some really beautiful songwriting here—none more so than on the simple ballad “I’ll Remember You.” Backed by legendary session drummer Jim Keltner and Mike Campbell and Howie Epstein on loan from the Heartbreakers, Dylan plays piano on this sweet expression of genuine affection for a past love. Campell’s guitar and Madelyn Quebec’s gospel backing vocals are a model of restraint here in an era prone to excess, and when Dylan leans into that vocal bridge (“Didn’t I try to love you? / Didn’t I try to care?”), we question neither his sincerity nor just how powerful his singing can be. A one-time concert staple well into the ‘90s, perhaps the song’s finest hour came during a dramatic montage in the 2003 Dylan-starring cult film, Masked and Anonymous.
Definitive Dylan: “Though I’d never say / That I done it the way / That you’d have liked me to / In the end, my dear, sweet friend / I’ll remember you”
“What Was It You Wanted” (Oh Mercy, 1989)
There’s not much meat left on the bone when talking about Oh Mercy. And that’s understandable. It’s not fair to say that Bob Dylan had left a ravenous fanbase starved for good songs for more than a decade leading up to this release. However, it is accurate to say that Oh Mercy marked the first album in that span that seemed to make sense to critics and listeners alike. Teamed with producer Daniel Lanois, Dylan’s latest batch of songs were sharp, economical, often mystical, and not suffering any fools. Even outtakes from these sessions of elusive studio cuts like “Dignity” and “Series of Dreams” would become fan favorites from the era. One song that didn’t seem to get devoured right away, though, was penultimate track “What Was It You Wanted.” It’s a driving, murky groove that finds Dylan playing bad cop in a relentless line of questioning to get to the bottom of things—in this case, what pieces of himself people feel entitled to. Dylan’s biting delivery, punctuated by a ghostly harmonica between verses, ratchets up the intensity as he searches for an answer that’s likely to never come. Dylan revisited “What Was It You Wanted” on 2023’s Shadow Kingdom, as telling a sign as any that we might’ve missed something the first time ‘round.
Definitive Dylan: “Has the record been breaking / Did the needle just skip / Was there somebody waiting / Was there a slip of the lip?”
“Handy Dandy” (Under the Red Sky, 1990)
There exists a small, but ardent patch of Dylan fans who’ve made it their mission to defend Under the Red Sky. That seems like a curious hill to die on, but it takes all types to make a fanbase. By all accounts, the recording sessions were miserable. Dylan felt completely disenchanted with the industry at the time and was stretched paper thin by pulling double-duty as a Traveling Wilbury. The result is an album of half-baked nursery rhymes, pointless cameos, and slick rock production that does these slight tunes zero favors. However, a couple keepers crept in, the least celebrated of which remains “Handy Dandy.” This bubble gum-snapping character study of an enigmatic, walking contradiction — maybe a fellow musician—finds Dylan in high spirits, delivering some of his most playful phrasing as old friend Al Kooper’s swirling Hammond organ bursts out of the gate in “Like a Rolling Stone” fashion. You can read whatever meaning you want into Handy’s circumstances, but the real joy here comes from just hearing Dylan sound happy making music again.
Definitive Dylan: “Handy Dandy, controversy surrounds him / He been around the world and back again / Something in the moonlight still hounds him”
“Dirt Road Blues” (Time Out of Mind, 1997)
I’m not sure even Bob Dylan knew that he had a record in him four decades into his career as formidable as Time Out of Mind turned out to be. His best work since 1975’s Blood on the Tracks by a country mile, this album spends no time pussyfooting around as Dylan delves deep into the darkest parts of human nature. It’s an unnerving record rife with alienation and paranoia, mired in heartache and despair, and steeped in confusion and questions of mortality. The stakes could not be higher, and Dylan wastes nary a note nor a word cutting to the core of matters. Perhaps lost in all these long shadows bumps along the little, improvised country blues number “Dirt Road Blues.” Saturated in producer Daniel Lanois’ signature swampy production, a muffled Dylan sounds less like he’s hitchhiking down that dirt road and more like he’s buried six feet beneath it. Jim Dickinson’s whirring work on the keys gives the tune just enough manic energy to make it a fit on this record. Sadly, “Dirt Road Blues” remains the lone track off Time Out of Mind that Dylan has never dusted off live.
Definitive Dylan: “Gon’ walk down that dirt road until my eyes begin to bleed / ‘Til there’s nothing left to see / ‘Til the chains have been shattered, and I’ve been freed”
“Floater (Too Much to Ask)” (“Love and Theft,” 2001)
As a songwriter, Bob Dylan has flexed just about every muscle imaginable across the years. He’s taken up causes, proven himself to be a master storyteller, and dug into all aspects of love, fate, and human nature. However, when we think about him building worlds, say, on an album like Time Out of Mind, we’re usually talking about an intense vibe, a particular window on the world as seen through a pane of glass tinted to match Dylan’s particular mindset. But the songs on “Love and Theft” feel much less mysterious and vague. Almost like we’re listening to Bob Dylan composing through a game of SimCity. A song like the meandering “Floater (Too Much to Ask)” bobs along for just under five minutes, using seemingly random brushstrokes to paint such a specific image of a time, place, and way of life. As this old-timey amble escorts us through town on a summer day, we learn of local history, town politics, and the protagonist’s family tree while receiving pearls of wisdom that range from homespun maxims to playful joshing. It’s a fascinating account that gives the drama of “Love and Theft” such a rich and worthy stage to play out on.
Definitive Dylan: “Romeo, he said to Juliet, ‘You got a poor complexion / It doesn’t give your appearance a very youthful touch!’ / Juliet said back to Romeo, ‘Why don’t you just shove off / If it bothers you so much’”
“Ain’t Talkin’” (Modern Times, 2006)
In a hypothetical game where we can save one closing song on a Dylan album from falling off the face of the earth, I’m reaching out for “Desolation Row” every last time. That said, if you tap out of 2006’s Modern Times a song early, you’ll have missed one of the most unnerving, mesmerizing performances of Dylan’s late era. “Ain’t Talkin’” pits the listener stride for stride alongside Dylan in a mysterious nocturnal tale full of quiet suffering, spiritual starvation, and moral agitation at what this world requires of him. It’s Dylan’s darkest piece since Time Out of Mind, a psychological burn that takes him from a mystic garden all the way to the end of the world. And to what ultimate end or fate? We’re not quite sure. Maybe these are the types of things Dylan thinks about when he’s just popping out to the corner bodega for a carton of milk and a newspaper. Then again, probably not.
Definitive Dylan: “Ain’t talkin’, just walkin’ / Through the world mysterious and vague / Heart burnin’, still yearnin’ / Walkin’ through the cities of the plague”
“I Feel a Change Comin’ On” (Together Through Life, 2009)
There’s something delightfully uplifting about hearing an older Bob Dylan feeling young at heart. Even if that youthfulness comes embedded in a highway paved with a lifetime of sadness, weariness, and dissolution. While album-mate “Forgetful Heart” has become a dramatic performance piece in concert, Dylan’s jaunty stroll through “I Feel a Change Comin’ On” might be the real gem of this 2009 collection. Down in the groove again with Grateful Dead lyricist Robert Hunter, Dylan surveys the road both behind and ahead as David Hidalgo’s accordion escorts him, blowing like the wind through the singer’s trademark curls. As Dylan laments how dreams never quite turn out and offers his baby some space in his suitcase to pack her things, we get the sense that he’s following the signposts towards Serenity, maybe the best destination one can hope for from a life that so often disappoints.
Definitive Dylan: “I’m listening to Billy Joe Shaver / And I’m reading James Joyce / Some people, they tell me / I’ve got the blood of the land in my voice”
“Narrow Way” (Tempest, 2012)
Shakespeare scholars sounded the alarm back in 2012 when it was revealed that Dylan’s upcoming album would share a title with The Bard’s final play. Groundlings, like myself, just made snotty posts about the C-minus school-project aesthetic of the record’s album art. Luckily, you can’t judge an album by its cover, and Tempest, though far from a perfect storm, gave no inkling of Dylan’s creative bluster starting to wane. I mean, the man recorded 45 stanzas about the Titanic for the title track. (Golf claps, anyone?) Nowhere on Tempest, though, does Dylan sound more potent than on the grinding 15-bar blues of “Narrow Way.” Its elastic groove slingshots back and forth as Dylan pours a hard life’s worth of wisdom, disbelief, and venom into this careening, seven-minute joyride. Surprisingly enough, Dylan has still never played “Narrow Way” live. Maybe one of these days he can give “Early Roman Kings” a night off?
Definitive Dylan: “We looted and we plundered on distant shores / Why is my share unequal to yours? / Your father left you, your mother, too / Even Death has washed his hands of you”
“Goodbye Jimmy Reed” (Rough and Rowdy Ways, 2020)
It’s probably way too early to say so long to “Goodbye Jimmy Reed.” The roughest and rowdiest cut by far off 2020’s Rough and Rowdy Ways got steady work the last few years on the road as the lead-in to set closer “Every Grain of Sand.” However, it appears that Dylan has, at least temporarily, retired the album after four years of exhaustive mileage. If one song makes a return, though, it needs to be this Dylan nod to the late blues legend. On a record more tame than rough and tumble, Dylan reminds us just how much fun it still is to hear him barking and calling it like he sees it over a thumping country blues crunch. It’s rough and ragged enough to have been leftover from the Blonde on Blonde cutting room floor, and Dylan’s growl sounds like it’s shed two decades of wear. Here’s hoping it’s not goodbye. Just see ya later, Jimmy.
Definitive Dylan: “Transparent woman in a transparent dress / Suits you well, I must confess / I’ll break open your grapes, I’ll suck out the juice / I need you like my head needs a noose”
