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Top 10 Bob Dylan Bootleg Albums

Bob Dylan
Evening Standard, Hulton Archive, Getty Images

Columbia Records has released nine official volumes of Bob Dylan bootlegs that cover everything from outtakes to concerts to demo recordings. But ‘The Bootleg Series’ only skims the surface of Dylan’s mad output of unreleased music over the past 50 years. That’s where the real bootleggers step in. In fact, the first mass-produced bootleg album, 1969’s ‘The Great White Wonder,’ featured two dozen unreleased Dylan tracks spanning the decade. Since then, hundreds of bootlegs have turned up, documenting nearly every song, fart and onstage mumble Dylan’s let loose over the years. Our list of the Top 10 Bob Dylan Bootleg Albums boils them down to the essentials.

Bob Dylan Highway 61 Revisted Again


‘Highway 61 Revisted Again’




‘Highway 61 Revisted Again’ (sic) recreates one of Dylan’s best albums with alternate takes from the 1965 sessions, but not in the proper sequence. It also adds a few extra songs that were recorded at the time, including ‘Please Crawl Out Your Window’ and ‘Positively 4th Street,’ both of which were released as singles after ‘Highway 61 Revisited’ came out.


Bob Dylan Genuine Bootleg Series


‘The Genuine Bootleg Series’




The first official ‘Bootleg Series’ box from 1991 includes the first three volumes in the the series and nearly 60 prime studio outtakes that cover 30 years. Apparently that’s not good enough for the folks who assembled a trio of three-disc sets made up of studio leftovers and live cuts covering roughly the same period. They make great companion pieces.


Bob Dylan Pllymouth Rock


‘Plymouth Rock’




Starting in October 1975, Dylan’s Rolling Thunder Revue — a caravan of friends and musicians including ex-girlfriend Joan Baez and former Byrd Roger McGuinn — played nearly 60 performances. This album gathers seven cuts from the first show of the tour from Plymouth, Mass., where he previewed songs from ‘Desire,’ which wouldn’t be released for another couple of months. Another nine tracks come from a Connecticut concert two weeks later. They all sound great.


Bob Dylan Folksinger's Choice


‘Folksinger’s Choice’




A few months before his self-titled debut album was released in 1962, Dylan played a New York radio show where he performed his own songs plus some traditional folk numbers. The music is excellent, but ‘Folksinger’s Choice’ includes a playful conversation with host Cynthia Gooding between songs — a real treat and rarity, even among the Top 10 Bob Dylan Bootleg Albums.


Bob Dylan Dylan Cash Sessions


‘The Dylan / Cash Sessions’




While recording ‘Nashville Skyline’ In early 1969, Dylan and Johnny Cash got together in a Nashville studio and played a bunch of songs — some Dylan’s, some Cash’s and some old country tunes. The performances are unstructured and often unfinished. But this historical summit between two legends is pretty awesome.


Bob Dylan In Concert


‘In Concert’




In 1963, between Dylan’s second and third albums, Columbia Records was all set to release a live record culled from a pair of NYC performances. It was pulled at the last minute, allegedly because Dylan and the label couldn’t come to a compromise on the opening track, ‘Last Thoughts on Woody Guthrie,’ a six-minute poem about the folk icon. This bootleg restores the unreleased album, right down to the cover.


Bob Dylan Freewheelin' Bob Dylan Outtakes


‘The Freewheelin’ Bob Dylan Outtakes’




Like he’s done throughout his career, Dylan recorded more songs than he needed for his second album. Good thing — first pressings of the record were pulled and four tracks were replaced. The 15 songs included on this great collection could easily have been compiled for another terrific Dylan album. It’s a wonderful chronicle of an artist finding his voice.


Bob Dylan Thin Wild Mercury Music


‘Thin Wild Mercury Music’




Like the No. 10 album on our list of the Top 10 Bob Dylan Bootleg Albums, ‘Thin WIld Mercury Music’ includes outtakes from ‘Highway 61 Revisited.’ It also includes leftovers from the two other terrific albums Dylan recorded in a whirlwind 12 months: ‘Bringing It All Back Home’ and ‘Blonde on Blonde.’ You may recognize some of the titles, but Dylan reworks the tunes into completely different songs.


Bob Dylan Blood on the Tracks New York Sessions


‘Blood on the Tracks: New York Sessions’




Dylan rarely used initial arrangements on the released versions of his songs — just scan any of the outtakes collections in our list of the Top 10 Bob Dylan Bootleg Albums for proof. In September 1974, he recorded ‘Blood on the Tracks’ in New York with studio musicians. The album was all ready to be shipped when Dylan returned to Minneapolis, entered a studio with local players and re-recorded the entire album. The official ‘Blood on the Tracks’ features cuts from both sessions; this excellent bootleg collects those earlier takes.


Bob Dylan Tree With Roots


‘A Tree With Roots: The Genuine Basement Tapes Remastered’




Dylan holed up with his old backing group the Band for three months in 1967. They batted around new songs (some ended up on Dylan albums, some ended up on Band albums, some were never heard from again) and goofed around on some old country and rock classics. Columbia released a two-record set of highlights from the loose sessions in 1975, and it’s an essential LP. But this four-disc, 128-track collection documents, almost in full, one of Dylan’s most pivotal periods.


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