Since 1991, Bob Dylan has been gifting his fans with bootleg compilations of session demos, song outtakes, live rarities and hidden gems once left off of major albums. Over the last 32 years, there have been 17 volumes of the infamous Bootleg Series, chronologically expanding the universes of every major era in Dylan’s career, from his time rambling through the Greenwich Village folk revival scene to his reclusive period after a motorcycle accident to the most recent retrospective: the years of Time Out of Mind and ”Love and Theft”.
It should be no surprise that someone as prolific as Dylan, who has released 39 studio albums since 1962, has more songs written and recorded than he has space for. In a situation like that, a masterpiece is bound to be left off of a major studio release. In fact, Dylan has left, by our account, six masterpieces off of his records, only for them to be discovered through bootleggers and compilation releases. That’s what makes being a Bob Dylan fan so rewarding, though. Even his most well-versed disciples have much more of his career left to mine through.
For this list, we will be looking at Dylan’s best outtakes. Non-album singles will not count, so don’t be alarmed by the omission of “Positively 4th Street” and “Can You Please Crawl Out Your Window?,” two of his absolute best songs ever. Instead, we will be looking at tracks puzzlingly left off of albums and live songs that never got studio recordings. Here are 10 of Bob Dylan’s best hidden gems, ranked.
10. “Talkin’ Bear Mountain Picnic Massacre Blues” – 1962
Recorded in April 1962, “Talking Bear Mountain Picnic Massacre Blues” quickly became a staple in Dylan’s early live sets. Along with “Song to Woody,” it is one of the pre-Freewheelin’ Bob Dylan compositions that Dylan became defined by when he was garnering attention at clubs across New York. It’s a hilarious, near-six-minute song inspired by a newspaper article about the Harlem social club’s Father’s Day picnic trip at Bear Mountain State Park.
The incident included a large amount of counterfeit tickets getting sold, a boat becoming overfilled with eager picnic-goers and then a bunch of people getting hurt. Of course, Dylan embellishes the story with a smidge of his own elastic wit, confidently crooning about hating bears and brainstorming better and safer places to have picnics. “Dogs a-barking, cats a-screaming / Women a-yelling, men a-flying, fists a-flying, paper flying / Cops a-coming, me a-running / Maybe we just better call off the picnic,” he sings.
Though it was recorded for inclusion on Bob Dylan, “Talking Bear Mountain Picnic Massacre Blues” never made it onto the record, it found a place on two different Bootleg Series releases, as well as Dylan’s live album In Concert – Brandeis University 1963, which is the best version of the track, and his funniest.
9. “Dink’s Song” – 1961
The origins of “Dink’s Song” are relatively unknown. No songwriter has ever been credited for the composition, but ethnomusicologist John Lomax made the first iteration of the song in the early 1900s, when he traveled to a migratory levee-builder tent camp in Texas and recorded an African-American woman named “Dink” singing it. Lomax’s recording of the song has since been lost, but some of the most important folk figures, including Pete Seeger, Dave Van Ronk and Dylan, covered it during the genre’s post-war revival.
Though Van Ronk’s version (which, in the liner notes of Van Ronk Sings, he credits the song to Lomax and his wife Bess Brown) is what inspired its use in the Coen Brothers’ Inside Llewyn Davis, Dylan’s cover is an underrated grail within his vast, never-ending discography, even if it never found a permanent home on a record.
The song casts a story of yearning and loss, as a woman grieves a lover abandoning her. Though some of the lyrics have changed over the years, depending on the singer’s rendition, Dylan left them virtually unchanged from Lomax’s recording, which he claimed to have heard sung from Dink herself. “I had a man / Who was long and tall / Moved his body / Like a cannonball / Fare thee well, my honey / Fare thee well,” he sings. “Dink’s Song” is not just a focal piece of the folk songbook, it’s one of Dylan’s best translations of standards from the genre.
8. “Angelina” – 1980
Written for Shot of Love in 1980 but not released until 10 years later on The Bootleg Series Volumes 1 – 3, “Angelina” arose from the aftermath of his Gospel Tour earlier that year. It’s an allegorical song pondering whether love can outlast violence, told by Dylan through bends in language that only he could elicit.
For the most part, Dylan had all but abandoned his surrealistic portraits of the mid 1960s by 1980. “Angelina” combines the story of a woman who was kidnapped as a child and now seeks vengeance with sometimes-indecipherable language. That isn’t to say “Angelina” is not a masterpiece, because it quite certainly is one of Dylan’s best songs from the time period. How it didn’t make the final cut of Shot of Love is fascinating, given that it’s quintessentially better than every song that did make it onto that record, aside from “Every Grain of Sand.”
But alas, Dylan is a poet of immeasurable imagery and insurmountable misunderstanding. “When you cease to exist, then who will you blame / I’ve tried my best to love you but I cannot play this game / Your best friend and my worst enemy is one and the same, Angelina,” he sings. Does his character sympathize with Angelina? Does he love her too much to let her parish under the weight of her own vengeful determination? The song, with beautiful backing vocals from Carolyn Dennis, Regina McCrary and Clydie King, dares to not conclude with a serviceable resolution. “Angelina” is a piece of cynical, romantic storytelling that would have fit nicely on Desire, though its legacy remains forever caught in the ether between Shot of Love and Infidels.
7. “Farewell” – 1963
“Farewell” might sound like a folk standard from the Depression-era, but it was actually written and recorded by Dylan in early 1963. The song was made before The Freewheelin’ Bob Dylan was completed, but it’s said that Dylan instead considered putting it on The Times They Are a-Changin’. “Farewell” finally saw a release in 2010 when it was included in The Bootleg Series Vol. 9.
The take of “Farewell” that is readily accessible came from a demo Dylan made for M. Witmark & Sons; all of the takes from the The Times They Are a-Changin’ sessions were never finished. Dylan reportedly based the song’s conception off of “The Leaving of Liverpool,” an old British folk ballad, but changed the lyrics. There’s a story, though unconfirmed, that Dylan wanted to sing “The Leaving of Liverpool,” but couldn’t read the lyrics that Scottish folk singer Allan McLeod wrote out for him, so he wrote “Farewell” instead.
“Farewell” is a tune about wayward hope and love, as a man has to leave his lover behind but hopes to see her again. “I will write you a letter from time to time / As I’m ramblin’ you can travel with me, too / With my head, my heart and my hands, my love / I will send what I learn back home to you,” he sings. Dylan would quickly transition from the lyrical architecture of the folk songbook to his patented poetic meanderings, where songs would be stuffed to the brim with imagery. That’s what makes “Farewell” such a perfect document of everything pre-Bringin’ It All Back Home. Dylan wasn’t just able to make renditions of songs written years before him; he could offer his own translations that were truly unique.
6. “Tomorrow Is a Long Time” – 1963
Though it was recorded before The Freewheelin’ Bob Dylan was completed, “Tomorrow Is a Long Time” only exists on The Bootleg Series Vol. 9 and Greatest Hits Vol. II. The version we all know and love is from a concert on April 12, 1963, at Town Hall in Midtown Manhattan. Because of its inclusion in Dylan’s second greatest hits entry, “Tomorrow Is a Long Time” doesn’t have the mysticality of other bootleg tracks. However, it remains one of his prettiest songs.
The song was then re-recorded during sessions for New Morning, but that recording has become lost online (though it surely exists beyond the lore, tucked away someplace in a bootleggers stash). “Tomorrow Is a Long Time” is very akin to other love songs Dylan wrote around the same time, including “Don’t Think Twice, It’s All Right” and “Girl from the North Country,” but there’s something in its simplicity that stops you in your tracks.
Some of Dylan’s prettiest translations of adoration appear on “Tomorrow Is a Long Time.” It’s the first real, recorded instance of his ability to master the romantic quadrants of the American Songbook. “Yes and only if my own true love was waitin’ / And if I could hear her heart a-softly poundin’ / Yes, only if she was lyin’ by me / Then I’d lie in my bed once again,” he sings. “Tomorrow Is a Long Time” is a gem from Dylan’s folk revival era.
5. “Red River Shore (Version 2)” – 1996
The 17th volume of Dylan’s bootleg series, titled Fragments, chronicles the ins and outs of his studio time during what is now considered his greatest comeback, Time Out of Mind and its successor Love and Theft. After releasing some of the weaker albums in his catalog between 1985 and 1993, he took a four-year break from new albums. For reference, before 1993 he had never gone more than three years between releases (New Morning came out in 1970 and was followed by Pat Garrett & Billy the Kid and Dylan in 1973).
Time Out of Mind became Dylan’s greatest record since Desire and would even with Album of the Year at the Grammy Awards in 1998. Some of his strongest songs, like “Love Sick,” “Not Dark Yet” and “Make You Feel My Love” solidified that he was still our greatest living songwriter. That being said, Fragments was long awaited, as fans waited for an inside look into how Dylan was able to piece together such a heroic return to his singularity.
“Red River Shore (Version 2)” is the best song from Fragments that didn’t end up on a record. It would have fit nicely on ”Love and Theft”, but there’s something otherworldly about it now. Dylan was singing about spiritual themes in a secular way, and “Red River Shore” is mythical in that way, how the protagonist of the song grapples with unrequited love and feeling forgotten. “Now I’m wearing the cloak of misery / And I’ve tasted jilted love / And the frozen smile upon my face / Fits me like a glove,” he sings. Like many of Dylan’s outtakes, it’s a great track that, to him, wasn’t good enough to make an album, but to many others could have been the song that transformed an entire career.
4. “Blind Willie McTell” – 1983
Recorded in 1983 and released on The Bootleg Series Volumes 1-3, “Blind Willie McTell” is one of the tracks that failed to make it onto the final cut of Infidels. Dylan had based the song’s melody off of “St. James Infirmary Blues,” a jazz standard made popular by Louis Armstrong, and told the story of Blind Willie McTell, a Georgian Piedmont blues pioneer who revolutionized fingerpicking and the use of a 12-string guitar.
The song is an allegorical reflection on the slavery and American blues, something Dylan would explore on “High Water (For Charley Patton)” on Love and Theft and “Goodbye Jimmy Reed” on Rough and Rowdy Ways. With Dire Straits frontman Mark Knopfler on guitar and Dylan on piano, “Blind Willie McTell” properly emphasizes the songwriter’s comeback after a string of three evangelical records. It was a return to impassioned lyricism, using Southern imagery and Bible scripture to tell the century-spanning history of oppression in America.
Dylan disciples consider “Blind Willie McTell” as one of his best compositions, and for good reason. It’s not just a songwriting apex; it’s solidification that his 1980s were, in fact, a great chapter in his career. Even in 2023, it being left off of a major studio release is befuddling. Though, its album-less identity feeds deeply into its singularity, permanently solidifying it as a mystical, burgeoning echelon in Dylan’s genius.
3. “She’s Your Lover Now” – 1966
Originally recorded for inclusion on Blonde on Blonde, “She’s Your Lover Now” didn’t see a release until The Bootleg Series Volumes 1-3 in 1991. Its chord progression is similar to “Like a Rolling Stone,” but Dylan’s vocal performance is done in the style of “Stuck Inside of Mobile with the Memphis Blue Again.” The song took 12 hours to record, with 21 takes to choose from when it was all said and done. Unfortunately, Dylan hated all of them and cut the track off the album.
But undeniably, “She’s Your Lover Now” is one of Dylan’s sharpest lyrical performances. The track is poetic in the esoteric way that most of Blonde on Blonde is. “She’ll be standin’ on the bar soon / With a fish head an’ a harpoon / An’ a fake beard plastered on her brow / You’d better do somethin’ quick / She’s your lover now,” he sings. The track is chaotic and cluttered, but in a linguistically harmonious way that only Dylan can pull off.
Through mermaid imagery, castles and lost memories, “She’s Your Lover Now” is the closest thing we have to a Bob Dylan fairytale. Yet even that label feels unfit. The song gnaws away at you, as there’s something angry about its sound, even through all of its mysticality.
2. “Up to Me” – 1974
The mystery of why “Up to Me” was left off of Blood on the Tracks remains unsolved. Though the album is widely considered a masterpiece, “Up to Me” might have skewed that designation, given how it contradicts the passive ethos sprinkled across the tracklist we all know and love. The song would later find a home on the Biograph box set in 1985, and later on Side Tracks and The Bootleg Series, Vol. 14.
Blood on the Tracks has long been associated with Dylan’s separation from his wife Sara Lownds. Even his son Jakob has called the record “my parents talking.” Dylan himself has disputed that the record is autobiographical, but he’s never been all that reliable. Nonetheless, “Up to Me” is a beautiful track echoing the melancholia of the album it was scrapped from. However, on the other songs on the record, Dylan’s character found himself in the throes of a heartbreak he couldn’t avoid. On “Up to Me,” his character is tasked with circumventing his despair; to be or not be alone is his choice.
“Well I watched you slowly disappear down into the officers’ club / I would’ve followed you in the door, but I didn’t have a ticket stub / So I waited all night ‘til the break of day, hopin’ one of us could get free / When the dawn came over the bridge, I knew it was up to me,” Dylan sings. There are 12 verses, each sharing the same refrain. In the context of his catalog, “Up to Me” is that one track that benefits more from being albumless. It sounds too much like a Blood on the Tracks song to have wound up on Desire, yet it doesn’t align with the storytelling perspective of the former. It’s the only Dylan song that belongs in the purgatory of bootlegs. “Up to Me” does not need a forever home; it transcends the confines of one article of time.
1. “Abandoned Love” – 1975
Recorded just before the Rolling Thunder Revue tour began, Desire quickly became an underrated stroke of genius in Dylan’s catalog. Of course, “underrated” means very little in the context of his work, as even the most hidden gems are dearly beloved by his loyal fans. But the record contains “Sara,” “Hurricane” and “Joey,” some of the greatest songs Dylan wrote in the 1970s, all often overlooked by the masterpiece of Blood on the Tracks. However, maybe the best composition from the Desire sessions, and one of the best in Dylan’s entire discography, is “Abandoned Love,” a heart-wrenching breakup song written in the wake of his separation from his wife Sara.
The one-two-punch of Blood on the Tracks and Desire gave listeners an intimate look at Dylan and Lownds falling out of love with each other. Dylan quickly perfected the protest song and the love song, but “Abandoned Love” is him at his most tortured: a man who has said every word imaginable but is now tasked with stringing them together in a way that might save his marriage or provide catharsis and clarity to its ending. “We sat in an empty theater and we kissed / I asked ya please to cross me off your list / My head tells me it’s time to make a change / But my heart is telling me I love ya but you’re strange,” Dylan sings.
It’s hard to tell what is more astonishing: That Dylan could write such a momentous and perfect depiction of heartache, or the fact that he had the gall to leave it off of a record altogether. “Abandoned Love” is the kind of track that makes Bob Dylan’s genius so influential in the history of modern music. To know his most popular songs is a gift, but to take the time to mine through the irreplicable gems, which come aplenty in numerous iterations across decades, is an act of loving discovery.
Matt Mitchell is Paste’s assistant music editor, and a poet, essayist, and culture critic from Northeast Ohio. Find him on Twitter @matt_mitchell48.
Listen to an exclusive Bob Dylan live performance from Bob Dylan & The Band at Boston Garden on January 14, 1974.