I can’t think of a series of physical media releases that I currently adore more, both conceptually and in execution, than the ongoing Bootleg Series issued by Bob Dylan and Columbia Records. Despite the ultimately large differences in my personal love for each, all of them are wonderful and probably essential listens for any Dylan lover. Somehow, they take his inextricable relationship with the genesis and continuing influence of the “illegal” bootleg and Great White Wonder and take them far further, all while feeling like not shameless cash grabs/commercial co-option but rather true labors of love.

These rankings, and even the categorization around the boundaries of each tier, aren’t terribly precise, but it’s worth noting that they’re graded along dual criteria: listening enjoyment and historical significance. My own tastes are different than many others, of course (Shot of Love is in my top 5 Dylan albums after all), but I do think this general order feels right; all the Curios — the name is meant as a compliment, and not a backhanded one either — are extremely fascinating and lovely works in and of themselves. These are all evaluated based on my first (give or take a couple) listens of the standard editions, typically composed of two CDs, and don’t take into account any ancillary material like the booklets.

MASTERPIECES

Vol. 13: Trouble No More, 1979-1981

Vol. 16: Springtime in New York, 1980-1985

Vol. 11: The Basement Tapes Raw

Vol. 8: Tell Tale Signs: Rare and Unreleased, 1989-2006

Vol. 10: Another Self Portrait (1969-1971)

Volumes 1-3: (Rare & Unreleased), 1961-1991

TREASURE TROVES

Vol. 17: Fragments: Time Out of Mind Sessions (1996-1997)

Vol. 5: Live 1975: The Rolling Thunder Revue

Vol. 4: Live 1966: The “Royal Albert Hall” Concert

Vol. 14: More Blood, More Tracks

CURIOS

Vol. 15: Travelin’ Thru, 1967-1969

Vol. 9: The Witmark Demos: 1962-1964

Vol. 12: 1965-1966: The Best of the Cutting Edge

Vol. 6: Live 1964: Concert at Philharmonic Hall

Vol. 7: No Direction Home: The Soundtrack

Volumes 1-3: (Rare & Unreleased), 1961-1991

Realistically speaking, if these were considered as individual volumes, their placement in these rankings would be wildly different: Vol. 1 would be towards the bottom, Vol. 2 likely wouldn’t still leave the Curios tier, and Vol. 3 would be a healthy Treasure Trove. But taken together, this is a completely remarkable achievement, a full summary of Dylan’s entire oeuvre thus far and nearly indefatigable in its search for tracks both expected and unexpected. The inclusion of “Blind Willie McTell” and “Series of Dreams” alongside stuff like “I Shall Be Released” and the 3/4 “Like a Rolling Stone” acts as a validation of then-late Dylan; even if the amount of tracks is a little smaller, the straight run-through of Infidels outtakes lands like a sledgehammer. And there’s even room for surprises to a Dylan fan of like myself among the first two volumes, “Last Thoughts on Woody Guthrie” most of all. Really just a total triumph, with an impact and breadth even greater than the sum of its parts.

Vol. 4: Live 1966: The “Royal Albert Hall” Concert

This and its successor (and that volume’s successor to a much lesser extent) are a little difficult for me to evaluate, considering that I listened to them a number of times many years ago, when my Dylan interest was strictly limited to the ’60s and 1975-76. Still, this really is a great live album, well balanced along the acoustic and electric halves, and engrossing as a clearly audible evolution of energy and tension until the enormous release of “Like a Rolling Stone.” For historical value alone this must place in at least mid-tier, the true apex of the electric period controversy, but Dylan is inspired, clearly headed for a crash under the intense spotlight that dogged him throughout the tour but giving it his all. The Hawks/Band are great as well, “Tell Me, Momma” was probably the first non-studio Dylan song I ever heard and is a perfect way to start disc 2, and I love the little blast of “God Save the Queen” after he’s already left too, a reminder of where we are and a sudden calm reckoning after the storm.

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Vol. 5: Live 1975: The Rolling Thunder Revue

The gulf between this and Hard Rain, at least quality-wise, really isn’t as different as many say, but there’s something infectious about the exuberance displayed throughout here, and for all the complaints about this not being taken from a single concert like the surrounding volumes, the hodgepodge nature works to its benefit as a reflection of the ragtag brilliance that typified the Rolling Thunder Revue. “Tonight I’ll Be Staying Here With You” is so electrifying that I often forget it was originally on Nashville Skyline, and in many ways my enormous cooling on Desire actually helps me love the openness and unrestrained fun here. Again, the relative familiarity makes it hard to rate this, and the historical significance is a little tempered considering the existence of other documents of the RTV and its prominence in Dylan’s legend, but as a collection of music it’s never not transporting.

(I’m not counting the DVD that originally came with this; cool to see Dylan playing “Tangled Up in Blue” and to have the Biograph version of “Isis,” though it’s annoying “Romance in Durango” isn’t here, but it’s fairly inessential after everything else on this set.)

Vol. 6: Live 1964: Concert at Philharmonic Hall

I’m probably underrating this one, and it’s really a testament to the strength of the other volumes that this has to settle for second-to-last. The thing that totally escaped me before is how much this is a document of Dylan essentially on top of the folk music world. Consequently, he spends much of it in quite welcome goof-off mode, forgetting the first verse of “I Don’t Believe You,” bantering with the audience (the “Mary Had a Little Lamb” quip is especially choice). His incorporations of Bringing It All Back Home material adds several layers of historical significance; on the other end of that spectrum, the duets with Joan Baez are just lovely, to the point where he simply provides accompaniment on one song. Not as varied as the other releases, but on pure mood alone, this is a great time.

Vol. 7: No Direction Home: The Soundtrack

This is the release that I really don’t know what to do with. I haven’t yet seen Scorsese’s documentary, but as is this exists in a weird space, quite nearly superseded by not one but two volumes: 1-3 in its attempt to tell the story of Dylan, which is a much narrower portrait that only runs to the motorcycle crash; and 12, in its extensive reliance in disc 2 on 1965-66 studio outtakes. I listened to it a second time and think it flows a bit better, but the inclusion of “Song to Woody,” an honest-to-God studio album track, takes up space on what’s supposed to be a bootleg (even if it is the perennially underrated debut), a decision which rubs me the wrong way, as does the usage of 4’s closer to a lesser degree (surely there was some other final performance that would have worked as well). Not a misfire, and listening to Dylan’s evolution even in micro form is still fun, but this is the one that I don’t think has quite the same clear-cut raison d’être that every other volume has.

Vol. 8: Tell Tale Signs: Rare and Unreleased, 1989-2006

Quite conceivably the most important release to the identity of the Bootleg Series aside from 1-3; not only does this introduce the deluxe edition concept that every release from 10 on embraced, but it also redirects the focus of the series from live records or career overviews to a laser focus on a specific period of his creativity. That period here, while still larger than the others, is just chock-full of great songs, and especially coming after the familiarity of 7, the pure blast of energy of “Mississippi” and expert flow makes this a total joy to listen to. The inclusion of multiple versions of the same song also highlights the mutability and constant experimentation that truly comes to the fore with this installment going forward, as does the canny incorporation of fantastic live cuts. The reintroduction of track-by-track notes is more than welcome (though sadly not universally adopted); “‘Cross the Green Mountain” is the exact right slightly odd way to end too. As a realignment in multiple ways and a collection dedicated to such different eras that nevertheless feels so concentrated, this is a total success.

Vol. 9: The Witmark Demos: 1962-1964

Notwithstanding its clear historical significance, I initially had this solidly in second-to-last place, thinking that the comprehensiveness made for something of a slog, but a relisten really helped me love this more. The collection, similar to something like the Basement Tapes, benefits from simultaneously seeing the demos as embryonic forms that would be elaborated on further and as a vibe in and of themselves, the chronological flow across songs signaling a development in songwriting that’s become rather palatable for me to track anew. There’s also just a charm in hearing such a young Dylan interacting with the producers, his eagerness breaking up the songs without interrupting the mood. Much stronger as a unit than I had previously given it credit for.

Vol. 10: Another Self Portrait (1969-1971)

For me, Self Portrait isn’t an album in any need of improvement, but what’s so great about this collection is that all the removal of overdubs and so on and so forth only helps emphasize the brilliance of the original. Dylan’s voice comes to the fore, as does his clear passion for his varied material, and the little bits of contextualization — a Nashville Skyline outtake here, a Basement Tapes cut there — work beautifully to frame the sessions that produced both one of Dylan’s best albums and one of his worst. The latter’s alternate takes are near-uniformly better than their approved counterparts; this even manages to redeem “If Dogs Run Free” for God’s sake. I don’t know if this is quite as revelatory as many of its tier fellows, but ending with maybe my favorite Dylan recordings, the “When I Paint My Masterpiece” demo, is such a bold and perfect move. “Masterpiece” on a masterpiece about a masterpiece: couldn’t be more fitting.

(I still wonder why the deluxe edition only includes the invaluable Isle of Wight concert and the baffling choice to throw in a remastered Self Portrait, though I haven’t listened to it yet and it may be markedly different; wish it didn’t seem so lean but that’s not included in the evaluation.)

Vol. 11: The Basement Tapes Raw

This selection carries with it an enormous asterisk; it can be convincingly argued that this is the sole bootleg whose canonical/standard edition is The Basement Tapes Complete; it’s not given a Deluxe classification, it’s the name of the article/listing on both Wikipedia and Discogs, and arguably the entire reason for this release is the completeness. I haven’t listened to the six discs yet, which could either be a bit wearying or #1 by a mile (I’m banking on the latter), but Raw is totally essential in and of itself, not just because it has the track-by-track notes that Complete understandably lacks. The decision to include outtakes, alternate tracks, restored tracks, and tracks without overdubs all in one basket is inspired, not least because it encourages the listener to constantly look back and reconsider these tracks built upon their underground status. I’ve talked about my enormous issues with the ahistoricity and futzing of the original The Basement Tapes, and even Raw makes enormous strides towards correcting them, bringing these songs and recordings back into the light where they ought to have been forty years earlier. While I wouldn’t want to just own this one (and don’t), the standard and deluxe make for a great pair that reinforce each other, and this one has immaculate vibes, a dream to listen to and savor.

Vol. 12: 1965-1966: The Best of the Cutting Edge

This also poses some of the same categorization problems as its predecessor; I don’t expect I’ll ever listen to the Collector’s Edition and it’s safe to discount that, but the Deluxe Edition doesn’t have the awkward “The Best of” specification. There are reasons to put down this collection: the weird contrivance of three separate editions, a slightly redundant return to the electric period well, my insanely petty gripe that it’s the only one where the booklet is so thick (without track-by-track notes I might add) that it and the jewel case have to swap places in the cardboard slipcase. All that being said, this is still a terrific collection of music, albeit with more inessential outtakes and a little less focus and dynamism than most others post-8. It might be that these songs are *too* iconic for the differences in alternate takes to truly register, notwithstanding the real frisson of “Bob Dylan’s 115th Dream” proceeding in acoustic after the false start that’s on the real album. Even on second listen, I have a lot more fun with the more varied Blonde on Blonde recordings (that chugging “Visions of Johanna”!) well into disc 2, and that’s taking into account that it’s one of my very favorite Dylans. But this isn’t a hard listen at all, and I’m in the presence of some of the greatest songs ever recorded, so this can’t be all that low; breaking the continuity with the last giggle-fit track is a pleasingly playful touch.

Vol. 13: Trouble No More, 1979-1981
An astonishingly big swing in all ways: an album of nothing but live performances for the first time since the early bootlegs, a focus on the infamous Christian period, all coming off of the bootleg dedicated to his most beloved era. This is my favorite, with only 16 as a close rival, in large part because the Christian period genuinely might be my favorite at this point. But this is also among the most historically significant releases, with as radical rearrangements as 8, as complete a reconceiving of a period as 10, a band on as much fire as 5. The very fact that the songs that get two versions are the expected “Slow Train” and “Gotta Serve Somebody” and the totally unexpected (to me) “Solid Rock” just demonstrates how intelligent this is as a collection of music. Even the exclusion of a few Shot of Love songs is more than made up for by a number of amazing unreleased songs, especially the immortal “Ain’t Gonna Go to Hell for Anybody.” That this represents the fullest depiction yet of how Dylan’s songs will evolve across a tour is just icing on the cake; the existence of numerous releases of studio outtakes from this era, especially on 1-3, makes this live swerve all the more appropriate. He’s never sounded more fiery or surprising than this, and I couldn’t be more grateful for such a labor of love.

Vol. 14: More Blood, More Tracks

It’s both annoying and entirely reasonable that this is the only Bootleg thus far (hopefully the only one) that only has one disc in the standard edition. On one hand, it messes up the cardboard slipcase aesthetic continuity and it’s much more annoying to take the booklet out of the jewel case. On the other, while this runs into the same problem as 12 — the songs are too iconic, coupled with the inclusion of acoustic tracks already on 1-3 — there’s still the fact that I’m listening to some of the greatest and most penetrating music ever recorded. With just one take for each song — really wish “Call Letter Blues” was thrown on to complete the collection — this still achieves the same consistent mood that, say, 12 and 9 have without ever getting monotonous; the full New York sessions can stay on the deluxe edition, while these represent something of the cream of the crop, a setup akin to my beloved 11. Maybe I don’t have the best idea of how to rate this (it really is short after all, perhaps too much so to be a true treasure trove) but it’s just great music that doesn’t overstay its welcome at all, each take ringing with possibility.

Vol. 15: Travelin’ Thru, 1967-1969

Conversely, I have no clue why this of all bootlegs needed to be three discs, given that there’s actually less music all together than some of its two-disc brethren, though ultimately that doesn’t mess with the continuity nearly as much as 14; it is strange that there’s no deluxe edition though, especially since there’s so many takes that aren’t on here. Regardless, while this probably has a similar relative lack of dynamism as 12, the comparative strangeness of the music here helps elevate it, as does the canny segmentation. This entire period has some of the most pleasant vibes of Dylan’s entire career (alongside of course 11), and this bootleg is a great representation of that, floating along through the unexpectedly great and fascinating Dylan/Cash sessions, all the way to the surprisingly engaging Earl Scruggs cappers.

Vol. 16: Springtime in New York, 1980-1985

Among other things, this is just utterly brilliant as almost a direct rejoinder to 1-3, acting as a remake and embellishment on all those Infidels outtakes. Performing the incredibly valuable duties of establishing both Infidels and Empire Burlesque as two great albums that could have been masterpieces, it also finds one of the most cogent justifications for the entire series, each of the seven common tracks between it and 1-3 chosen to provide an alternate picture of an alternate picture, fully capable of standing on its own but also encouraging the listener to go back and forth, finding a synthesis of Dylan in this incredibly fertile but also compromised period. In that sense, it’s as full a reinvention of a reviled period as 10 and 13, doing so with both those works’ predilection for new arrangements (so much Empire) and by including substantial outtakes, “Too Late” being the crown jewel (a similar approach that 11 applied to a much more popular time). The decision to end with first “New Danville Girl” and then the other take of “Dark Eyes” is primo Dylan sequencing as well. This is as joyous and revelatory as any edition; on some days it might as well be my favorite.

Vol. 17: Fragments: Time Out of Mind Sessions (1996-1997)

First things first: the new remix of Time Out of Mind is as valuable a service as any the Bootleg Series has ever offered. I go back and forth on the original album (though it’s always been great), but drained of the Lanois swamp this version just sparkles. The inclusion of a full studio album on a bootleg, however, kind of unbalances it, or at least makes it a strange object when compared to the semi-hodgepodge concept of all the preceding entries. It almost feels too polished in a way, too obviously great when compared to the relative modesty of the series as a whole; if there’s a mammoth quality to 11 Complete or 14 Deluxe, that’s created by historical reputation rather than an artist’s canon. More pertinently, it means just one disc of outtakes/alternate takes, though it functions almost akin to 14’s single disc; once again I wish “Dreamin’ of You” and “Marchin’ to the City” were on it to complete the set (intriguingly there’s no alternate studio “Million Miles” even in the Deluxe). But the alternate versions here are vastly different and stripped down, there’s yet another version of “Mississippi,” and listening to them just after a more official version adds another valuable lens. Definitely a fascinating experience, and its revision’s brazen lack of precedence is something to be treasured; a real blast to listen to.