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How Bob Dylan landed his first recording session 60 years ago

It was 1961 in New York City, and a 20-year-old named Bob Dylan was recording his first album.

“What I remember is this scruffy little kid sounding like he was 80 years old. And I was astonished,” Billy James, a young publicist for Columbia Records at the time, told The Post. He was working at the label’s Midtown Manhattan office when he got called to the upstairs studio to see the new guy. “I’d never seen or heard a performer like that before.”

He may have sounded 80 years old then, but now Dylan is actually 80, and hitting the Beacon Theatre Nov. 19 exactly six decades since he began recording his debut album.

To get there, the stars had to align for this kid from Minnesota — born Robert Zimmerman — who first arrived in New York in January of 1961.

His lucky break came when he met Carolyn Hester, a folksinger from Texas who was four years older than him and had already established herself in the NYC folk scene.

Bruce Langhorne (from left), Carolyn Hester, Bob Dylan and Bill Lee at a recording session in September 1961.
photo credit: Don Hunstein

In a recent phone call, Hester described first meeting Dylan. She was onstage late one night for her third set at Gerdes Folk City, a club in the heart of the burgeoning Greenwich Village folk scene. “Here’s a song I like that was taught to me by Buddy Holly, it’s a song he wrote,” she said by way of introduction to “Lonesome Tears.”

Then, as Hester told The Post: “Well, this young guy with a cap on pulls his chair over to the stage and sits beside me. A wide-eyed Dylan goes, ‘Did you know Buddy Holly?’”

Hester had indeed done some work with Holly, a fellow Texan who died in a plane crash a few years earlier, in 1959. Dylan said Hester’s connection to Holly awed him: “That she had known and worked with Buddy Holly left no small impression on me,” he wrote in his 2005 memoir “Chronicles: Volume One.”

Dylan and John Hammond Sr. recording together in 1962.
Dylan and John Hammond Sr. making music together in 1962.
photo credit: Vernon L. Smith co

In those days, Dylan was playing whenever he could in New York, doing the rounds at Cafe Wha?, the Gaslight and Kettle of Fish. He knew that he needed a recording contract to take it to the next level, but he’d been rejected by two labels, Folkways and Vanguard.

That summer, a couple of months after Dylan met Hester, he heard that she was performing at Club 47 in Cambridge, Mass., which had its own Village-like scene.

Hester, there with her then-husband Richard Fariña, was surprised to hear about her opening act that night: “There was Bob Dylan, he was going to open for me. I didn’t know a thing about it.”

She invited him to join them at nearby Revere Beach with some other musician friends the following day.

“We’re sitting on the beach,” Hester said, “and Bob impressed me as being someone who probably never went outdoors … he’s got that wonderful curly hair and white, white, ghostly white [skin]. I’m four years older, and I’m feeling a little worried about him, like a big sister.”

Surrounded by musicians, Dylan tried to make connections, Hester said. “So Bob’s sitting there and starts saying, ‘Um, I’m looking for gigs, I’m having kind of slow time. I don’t have a record contract yet. Do you have any more gigs? Maybe I could join you.’”

Bob Dylan crouching in a recording studio in 1961.
Dylan made important connections that helped him land the contract for his first, self-titled, album in 1962.
photo credit: Don Hunstein court

But Hester wasn’t performing, she was about to make a record, having inked a deal with John Hammond Sr., the legendary music man who signed or produced Billie Holiday, Benny Goodman, Count Basie and Aretha Franklin.

She told Dylan she already had guitar and bass players (Bruce Langhorne, later an inspiration for “Mr. Tambourine Man,” and Bill Lee, father of Spike Lee). But her lawyer father had played harmonica on her first album; maybe Dylan could take his spot?

“I could do that, sure,” Dylan said, giving her his phone number.

Hammond came to a rehearsal of Hester’s newly formed band on Sept. 14. It was at the ground-floor apartment of a brownstone on West 10th Street where Hester and her husband were house-sitting.

“He couldn’t take his eyes off Dylan. He was struck by him right away,” Hester said.

A couple of weeks later came the Hester recording session — and a fortunate turn of events for Dylan. He had been opening for the Greenbriar Boys at Gerdes and got a rave review by Robert Shelton in the Times, calling him “A bright new face in folk music … one of the most distinctive stylists to play in a Manhattan cabaret in months.”

John Hammond Sr. and Bob Dylan in 1962.
John Hammond Sr. and Bob Dylan recorded more tracks together in 1962.
photo credit: Vernon L. Smith co

The review ran the day of the Hester session — she and Fariña read it on the subway ride uptown and showed it to Hammond when they arrived at the studio. “We didn’t want Dylan to have to pull it out,” she said of championing her new friend. 

When that recording session was finished, Hammond brought Dylan into the control booth and they talked. In Hammond’s office on Oct. 26, Dylan got his first contract.

On Nov. 20, Dylan, along with his girlfriend Suze Rotolo, arrived at Columbia’s Studio A, also known as “799” for its street number on Seventh Avenue.

John Hammond Jr., a blues musician who Dylan knew around the Village as Jeep — and who Dylan says he didn’t realize was his album producer’s son — was also at the session. Seventeen songs were recorded over two days. Of the 13 that made the album, titled “Bob Dylan,” only two were written by Dylan — “Talkin’ New York” and “Song to Woody,” an ode to his hero Woody Guthrie.

In her memoir “A Freewheelin’ Time,” Rotolo called Dylan “intense and unsure” in the studio. “Afterward he’d ask ‘What do you think, what did you think?’”

It was the senior Hammond who called James, the publicist, up to the studio that day. After the session, James was tasked with writing Dylan’s bio.

Bob Dylan recording in 1961
The November 1961 session didn’t make Dylan a star right away, but it convinced industry insiders that he was the real deal.
photo credit: Don Hunstein court

“He told me fanciful stories of his history,” James said, “about uncles who were gamblers, [knowing] blues singers from Navasota, Texas … I just went for it hook, line and sinker.”

James had been an actor in New York and a pal of James Dean. He said he recognized the same “charismatic quality” of Dean’s in Dylan.

The album was released on March 19, 1962. But Dylan wasn’t pleased with it: “I just wanted to cross this record out and make another record immediately,” he recalled of listening to an early copy in the Martin Scorsese documentary “No Direction Home.” “I thought I had recorded the wrong songs, and had already written a few of my own that I thought maybe I should have stuck on there.”

His concerns turned out to be well-founded: His debut did not sell well, topping out at around 5,000 copies that first year. At Columbia, some people referred to Dylan as “Hammond’s Folly.”

But even as he was recording his first album, Dylan was a-changin’.

“The Dylan … on that first record had become the Dylan of ‘Don’t Think Twice, It’s All Right’ and ‘A Hard Rain’s A-Gonna Fall’ — songs of his own composition that I am certain all prove immortal,” Sean Wilentz, Princeton University professor and author of “Bob Dylan in America,” told The Post.

Indeed, after 39 proper studio albums (his latest, “Rough and Rowdy Ways,” released by Columbia in 2020), Dylan, has certainly proven he is no folly.

Bob Dylan is playing at the Beacon Theatre, 2124 Broadway, at 74th Street, Nov. 19, 20 and 21.

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