Bob Dylan’s ‘Bootleg Series’ Ranked

Dylan just released the tenth installment of the "Bootleg Series," so we figured it was time to rank all of them.

By Brian Ives 

Bob Dylan recently released  The Bootleg Series Vol. 12: The Cutting Edge 1965-1966the latest installment in his long-running Bootleg Series.  Sometimes the series touches on the more celebrated eras of Dylan’s history, as the The Cutting Edge does, or 2014’s Volume 11: The Basement Tapes Complete. Other times, not so much (as with 2013’s Volume 10: Another Self Portrait 1969-1971).

That being said, Dylan’s fans are so diverse in the eras that they love, and they are so firm in their opinions, we’re sure Another Self Portrait was the Bootleg Series installment that some fans were waiting for.

And with that in mind, we’ll still dive in and rank all twelve volumes of the series.

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1. Volumes 1-3: Rare and Unreleased: 1961-1991 (1991)

In 1985, the career-spanning box set Biograph included a number of previously unreleased tracks, whetting the appetite for fans who were hoping for legit, commercial releases of other hidden gems from Dylan’s studio archives. The Bootleg Series Volumes 1-3 delivered that, and more. And while, on paper, this collection may seem as if it’s just for hardcore fans – after all, it’s a three-CD box set of all previously unreleased material – it turns out to be a great listen by any standard. There are some cool alternate takes of his songs here, notably “Tangled Up in Blue” and a piano version of “The Times They Are A’Changin’.” But the best part of the box set are the songs that Dylan never released:  some of his funnier songs (1962’s “Talkin’ Bear Mountain Picnic Massacre Blues,” 1963’s “Talkin’ John Birch Paranoid Blues”), songs that were recorded by other artists (1976’s “Seven Days,” 1971’s “Wallflower”) and one tribute to a baseball legend (1975’s “Catfish,” an ode to star New York Yankee pitcher Catfish Hunter). But the real highlights here include one of Dylan’s greatest songs ever, 1983’s “Blind Willie McTell” and his 1963 spoken word performance “Last Thoughts on Woody Guthrie.”

2. Volume 4: Live 1966: The “Royal Albert Hall” Concert (1998)

Fans may have been under the impression that the Volumes 1-3 box set was a one-off, but seven years after that release, Columbia Records put out the next installment of The Bootleg Series with this double live album, documenting one of Dylan’s most celebrated and controversial concert performances (this release also signaled that the Bootlegs would also include full concert recordings, not just studio outtakes). The concert, which had been heavily bootlegged, was actually recorded at the Manchester Free Trade Hall, but for years illegitimate bootlegs incorrectly stated that it was at the Royal Albert Hall, hence the quotes in the title. The first half of the show was Dylan as his folkie fans loved him: playing solo, with an acoustic guitar and his harmonica rack. But for the second half, he was joined by his backing band, the Hawks (who would later call themselves the Band), infuriating the purists. One fan famously yelled “Judas!” during that part of the show, which is audible on the album before “Like a Rolling Stone.” Historical significance aside, both halves of the concert are amazing. If you only own one live Dylan album (and we’ll admit that some of them are pretty dicey), let this be the one.

3. Volume 12: 1965-1966: The Cutting Edge (2015)

As mentioned above, different Dylan fans may favor different eras, but 1965 -1966 is one period that most fans (other than the die-hard folkies) will agree was incredible: it was the beginning of Dylan’s “electric” era. During that two year time span, Dylan recorded some of his greatest albums, 1965’s Bringing It All Back Home and Highway 61 Revisited and 1966’s Blonde on Blonde. Unlike Volumes 1-3 and Volume 4, this one is more for the hardcore Dylan fans. Comprised mostly of alternate versions of the songs from the aforementioned albums, it’s a bit like Pete Townshend’s Scoop series, which gave fans insight into the genesis of iconic songs. The standard version of this set, like most of the Bootlegs, is two CDs, although there is also a six CD version. And speaking of hardcore Dylan fans, only the most hardcore will want to spend time with disc 3 of the six disc set: it contains 20 different takes on “Like a Rolling Stone.” It’s almost surprising that an artist who has always enjoyed a veil of mystery is now willing to pull back that veil on one the most iconic songs in his catalog. (And the truly hardcore may want to check out a super-limited eighteen disc version of the box set for $600, including every note recorded during the ’65-’66 sessions, available only on Dylan’s website).

4. Volume 5: Live 1975: The Rolling Thunder Revue (2002)

Another double live album, documenting Dylan’s legendary 1975 tour. Unlike Volume 4, which contained a single live concert, this volume culled different performances from the “Rolling Thunder Revue” tour, which annoyed some fans. On the plus side: it’s a hell of a lot better than the live album recorded during the tour, 1976’s Hard RainThat’s probably because Hard Rain came at the end of the tour, when the rather large band seemed tired; this collection features earlier performances on the tour. The backing musicians were an odd conglomeration: who else but Dylan could get Byrds boss Roger McGuinn and Bowie’s guitar playing foil Mick Ronson in the same band? As with Volume 4, context adds to the enjoyment of the album, but it can likewise be listened to on its own merits. (Still, perhaps a Volume 5 version 2.o might be in order: fans have long complained about the lack of Dylan and Joan Baez’s cover of Johnny Ace’s “Never Let Me Go.”)

 

5. Volume 8: Tell Tale Signs: Rare and Unreleased 1989-2006 (2008)

While Dylan may not have owned the zeitgeist in the ’90s and ’00s, this collection points out he was still in full possession of his songwriting powers. It also shows how much great material came out of his collaborations with Daniel Lanois, who produced 1989’s Oh Mercy  and 1997’s GRAMMY winning Time Out of Mind. Besides the alternate versions of great songs like “Everything is Broken,” “Can’t Wait” and “Most of the Time,” there’s also songs that he held for later use (“Mississippi,” “Born in Time”), and there were also previously unreleased tracks, like the classic “Dreamin’ Of You,” a Time Out of Mind outtake. Next time anyone says Dylan hasn’t done anything since Blood on the Tracks , play them Oh MercyTime Out Of Mind, “Love and Theft” and Together Through Life. And then, once they’re blown away by that, play them this collection.

6. Volume 6: Live 1964: Concert at Philharmonic Hall (2004)

Dylan opened this show with “The Times They Are A’ Changin’,” and he wasn’t kidding around. A year later with the release of Bringing It All Back Home, he’d be leaving the folkies who attended this show in the dust, and some of the songs that he performed here would later get the full rock band treatment (“If You Gotta Go, Go Now,” “I Don’t Believe You”). Joan Baez joined him onstage at the end of this show, but you could hear him pulling away from his protest song roots during this performance. And like the other live concert recordings in this series, it’s easy to enjoy even without any context.

7. Volume 11: The Basement Tapes Complete (2014)

Before The Bootleg Series, there was The Basement Tapes. In 1967, Bob Dylan began recording prolifically in the basement of “Big Pink,” the house in upstate New York where the Band’s Richard Manuel, Rick Danko and Garth Hudson lived. Several of those songs ended up being recorded by other artists: Manfred Mann did “Quinn the Eskimo,” the Byrds did “You Ain’t Goin’ Nowhere,” and the Band recorded a few as well. But the Dylan/Band sessions ended up circulating to the public against the wishes of Dylan and his record company, as “Great White Wonder,” which is regarded as the first rock “bootleg” album. Dylan released a smattering of these recordings in 1975 as The Basement Tapes, but fans complained about cooler recordings on the bootlegs than on the version that Dylan released. Nearly three decades The Bootleg Series rectified this, via Volume 11. The standard 2 CD version contained a lot of great stuff, but completists went for the six disc deluxe set.

8. Volume 9: The Whitmark Demos: 1962-1964 (2010)

This is as stripped down as Dylan gets. Volume 9 collects the demos that he recorded for his first two publishing companies. Most of the songs would later be re-recorded for his albums but there’s a handful that had gone unheard for decades until this release. Some of the songs, like “Tomorrow is a Long Time” and “Seven Curses” ended up with other artists. A fascinating listen for Dylan fans, this one is pretty niche and isn’t for anyone but the hardcore.

 

9. Volume 10: Another Self Portrait (1969-1971) (2013) – Drawing from Dylan’s Nashville SkylineSelf Portrait and New Morning eras, this collection saw him covering traditional folk, more contemporary songs and doing some of his own songs as well.  Volume 10  features alternate takes, unheard covers and some unreleased songs, including “Only a Hobo” and “House Carpenter.” Again: only for the hardcore.

 

10. Volume 7: No Direction Home: The Soundtrack (A Martin Scorsese Picture) (2005) – As the title alludes to, Volume 7 doubled as the soundtrack to Martin Scorsese’s excellent Dylan documentary, No Direction Home. There’s nothing wrong with this collection: it’s filled with cool outtakes, alternate versions, demos and live stuff – but it just feels less special, given that better material was mined from Dylan’s ’60s era on other installments of the Bootleg Series. That said, his 1959 recording of “When I Got Troubles” is essential for any serious Dylan fan.

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