Don Hunstein

"He was moving so quickly," filmmaker D.A. Pennebaker says of Bob Dylan, the subject of his seminal, on-the-road documentary, Dont Look Back. Pennebaker tracked the songwriter through his 1965 U.K. tour, where his now-classic songs were reshaped each time he took the stage. "He almost seemed bored playing his older songs—songs that were only a year, or even a few months, old – he was developing so quickly. He'd already moved on. It was amazing to watch; almost magical."

That magic, with Dylan careening forward—developing the protest song as far as he could and then abandoning it; filling huge halls and holding audiences rapt with attention with just his voice and an acoustic guitar and then abandoning that for an electric guitar, Mike Bloomfield, Al Kooper and, eventually, The Band; and inventing the template for the modern rock star in the process—is in full flower on The Cutting Edge 1965–1966:The Bootleg Series Vol. 12, the new entry in Dylan's long-gestating Bootleg Series, out this Friday. The $600, 18-disc version set features every note Dylan laid down during that fertile, earth-shaking period, making him the first artist to give such unfettered access to the outside world into his creative process and the development of his craft, and even his persona.

"Almost within the first day or two, I found myself listening to the way he used language, which I thought was different," Pennebaker tells Esquire of the earliest days shooting Don't Look Back. "I thought, 'he's rewriting the way everyone after him will approach songwriting. This is a poet in the making.'"

The period covered by The Cutting Edge encompasses Dylan's seminal releases: Bringing It All Back Home, Highway 61 Revisited and Blonde On Blonde, a trifecta of albums that no artist has matched in the fifty years since their release. So many outtakes, studio chatter, and works-in-progress might sound less than intriguing to all but the most die-hard Dylan fan but, as you listen, and the story unfolds before you, the insight into Dylan's choices as a songwriter and artist are innumerable, and remarkable.

"When those albums were first released, the songs 'Subterranean Homesick Blues', 'Like A Rolling Stone' and 'Positively Fourth Street' were radical interruptions to the regular sound of the hit parade," Elvis Costello tells Esquire of that time, when he was only just toying with the idea of writing songs of his own. "These recordings (on The Cutting Edge) are fascinating for a number of reasons. They travel from a snapshot of a solo singer in the same room as some shambolic electric accompaniments to incredibly elegant record-making, whether accompanied by the fire and thrill of Mike Bloomfield or The Hawks (later known as The Band) or the greatest, most delicately articulated playing from the Nashville session Cats on Blonde On Blonde."

Listen to "It Takes a Lot to Laugh, It Takes a Train to Cry - Take 3" from The Cutting Edge, exclusively on Esquire:

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Perhaps the best example of that "fire and thrill" on the 6-disc version of The Cutting Edge are the four takes of "It Takes a Lot to Laugh, It Takes a Train to Cry", which keen listeners may recall as "Jet Pilot" from Dylan's 1985 Biograph box set. But here, Dylan, guitarists Mike Bloomfield and Al Gargoni, pianist Frank Owens, plus bassist Joseph Macho and drummer Bobby Gregg, attack the song on June 15, 1965 during the very first session for Highway 61 Revisited, with an aggression not usually found on major label recordings of the day. Dylan starts out on piano on Take 1, and the backing is tentative. But by Take 8 Gregg is pushing everyone forward and Bloomfield's guitar sounds like it's shooting sparks. A month and a half later, on July 29, with Al Kooper, first on organ and then second piano, the band truly finds its groove, on a soul-infused, hypnotic Take 3.

"I give a lot of credit to Albert Grossman," Pennebaker says of Dylan's oft-maligned manager of the time. "He loved Dylan and he loved that music. He would hang around all the time, and he was always there listening, and he was always supportive of what Dylan was doing, no matter what it was. And I thought, that's what an agent should be. I never even saw the Beatles agent when I was around them. Not once in my life. He was off making money somewhere and the Beatles were doing whatever they wanted on their own. I thought that Albert was invaluable to Dylan at that time."

And is all the hubbub around rejected recordings all too much?

"I don't know that you should 'lighten up' regarding the writer of 'Across The Green Mountain' or 'Not Dark Yet', let alone 'Masters Of War' or 'Every Grain Of Sand'," Costello says. "But I also see a hard-working traveling musician and showman, who just happens to be at the head of the column in two or three songwriting traditions." Dylan pops up regularly in Costello's recent memoir, Unfaithful Music & Disappearing Ink. He is a bona fide fan as well as a legend in his own right. And like most Dylan junkies will, he has a favorite track on The Cutting Edge. "My favorite cut is the intense, solo piano rendition of 'She's Your Lover Now'," he says of the 8 minute heart-stopper that was left off Blonde On Blonde. "The whole clambake is worth that one performance."

The 379 track, 18-CD numbered edition of Bob Dylan's The Cutting Edge 1965–1966: The Bootleg Series Vol. 12 and a are available this Friday, November 6. A newly of D.A. Pennebaker's Dont Look Back is out November 24.

Don Hunstein

Jeff Slate Jeff Slate is a New York City-based songwriter and journalist who has contributed music and culture articles to Esquire since 2013.

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