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60 years ago, Bob Dylan’s Boston debut was a freewheelin’ good time

Weeks before the release of his seismic ‘The Freewheelin’ Bob Dylan,’ the singer performed stunning new originals at a tiny Kenmore Square cafe.

Bob Dylan with Club 47's Betsy Siggins backstage at Jordan Hall in November 1963. Seven months earlier, Dylan's first headlining show in the city took place in a tiny coffeehouse near Kenmore Square. In the interim, he released "The Freewheelin' Bob Dylan," the album that catapulted him to the top of the folk music world.Photo by Dick Waterman, courtesy of Betsy Siggins

Sometimes there’s a very thin line between being a musical sensation and no one being certain exactly how you spell your stage name. If you were paying attention in April 1963 to newspaper ads for a pair of weekend shows at a Kenmore Square coffeehouse, you might not be certain if “Bob Dylan” or “Bob Dillon” was about to perform at Café Yana.

That spring 60 years ago, 21-year-old Bob Dylan was only just beginning to construct his monumental myth. His eponymous debut had been released 13 months earlier to a small, mostly warm reception, but he was far from being a household name. In the folk music circles of Greenwich Village and Harvard Square, however, he was an intoxicating curiosity who had manufactured his own rumors and origin stories until no one knew what was real and what wasn’t. His girlfriend, Suze Rotolo, for instance, had only recently learned his real last name — Zimmerman — when she spotted his draft card in their shared apartment.


An April 1963 Boston Globe ad misspelled Bob Dylan's name ahead of his two shows at tiny Café Yana.Boston Globe

Signed to Columbia Records and managed by Albert Grossman, Dylan was in the thick of recording his second album — “The Freewheelin’ Bob Dylan” — when he made his live debut in Boston. Its iconic cover image of Dylan and Rotolo walking down Jones Street in the West Village in the freezing cold dawn had already been snapped back in February. Released five weeks after the singer’s April weekend in Boston, “Freewheelin’” would introduce Dylan as a powerful songwriter to a rapidly expanding audience. It would completely capture the Beatles’ imaginations — they excitedly listened to the LP over and over — altering the way they’d approach songwriting, beginning with 1965′s “You’ve Got to Hide Your Love Away.” Within a year of the album’s release, Dylan would be back in Boston, this time selling out Symphony Hall.


Dylan had been to the city several times prior to that April 1963 weekend, but he had never enjoyed a proper venue booking. He had even been denied his own stage time at the it-folk venue, Club 47 on Mount Auburn Street in Cambridge — the scene rivalry between Greenwich Village and Harvard Square was very much real — and the singer-songwriter had only managed to appear before an audience there by convincing Carolyn Hester to bring him onstage during her set in August 1961. Without significant stage time to speak of, Dylan drank and swapped songs with New England folk musician Eric Von Schmidt at his apartment and, at one point, they found themselves in a backyard in West Roxbury, drunkenly trying to play croquet. “He was one of the most uncoordinated guys I’ve ever seen,” Von Schmidt told writer Anthony Scaduto. “He could just not make the mallet come in contact with the ball.”

The red-carpet-free Boston/Cambridge reception Dylan experienced in ‘61 was now transforming into a fevered, reverent welcome less than two years later. In the mimeographed pages of Broadside, Dave Wilson’s local biweekly folk music publication, a big reveal came a week before the Café Yana gig: “We couldn’t tell you his name then, but can now — Bobby Dylan. There is no other young performer today with as much magic surrounding his name. … As far as we know, this will be Bobby’s first Boston appearance — professionally at least.”

As for the club itself, it was nothing special, save for the music and people it attracted. Wilson recalls how dark it was inside Yana with its walls all painted black and its narrow corridor between tables and chairs leading to the small stage in back. Passing by it today — the coffeehouse at 50 Brookline Ave. occupied the rear portion of what is now the Cask ‘n Flagon — you certainly wouldn’t guess local music history was made there. Its capacity? Maybe 35 or 40 people.


On a small stage, stunning new music

Café Yana waitress Susan Bluttman clearly remembers Dylan and Rotolo walking into the venue together that Friday evening on April 19, asking where they could hang out before showtime. Bluttman showed them to the loft above the kitchen in back and asked Dylan if he would play “Blowin’ in the Wind” during his set. His recording of the song was not out yet, but he had performed it on TV a year earlier; still, Dylan was shocked by her request. “He looked at me like, ‘Where the [expletive] did you hear that song?’” Bluttman says, “and I told him that Buffy Sainte-Marie covered it when she performed at Yana a few months prior.” Dylan would oblige her request.

This song request was not the only pre-concert surprise waiting for Dylan in Boston. Wilson regularly aired live performances from Café Yana on his “Coffee House Theatre” radio program on MIT’s WTBS-FM. Apparently, no one told Dylan that his performance would go out live, and he became nervous when Wilson quietly spoke to him about it right before his set. “I knew what he worried about,” Wilson says, “that Albert Grossman would chew his ass out if he found out he performed on the radio for free.” Wilson managed to convince Dylan that the station had a weak campus signal and that not many people would even hear it.


The cover of "The Freewheelin' Bob Dylan"

The April shows at Café Yana were rounded out by a politically minded folksinger with a strong local following named Greg Hildebrand and New Bedford native Paul Clayton. By the close of the 1950s, Clayton had released nearly 20 full-length albums, specializing in New England sea shanties and Child Ballads. Dylan looked up to Clayton, and a friendship bloomed. Clayton would morph from mentor to something of a sidekick to the rising star. Remarking on Dylan’s uncanny ability to invent a song from whole cloth without an instrument in his hands — he once drove to a concert booking while Dylan sat in the back seat writing “Chimes of Freedom” — Clayton told mutual friend Barry Kornfeld he “thought [Dylan] had the devil in him.”

But by the time “It’s All Over Now, Baby Blue” was released in 1965 — some believe it was both a send-off to folk music and to Clayton — Dylan had exiled the singer from his inner circle without much of an explanation.

On the Yana stage, soon-to-be-released stunners were unveiled one after the other: “Girl From the North Country,” “A Hard Rain’s A-Gonna Fall,” and “Masters of War,” with its melodic blueprint unmistakably arising from the English ballad “Nottamun Town” (and potentially from a Boston connection, via local folksinger Jackie Washington’s cover of “Nottamun Town,” released in 1962). At this time, Dylan sang songs about impending nuclear war and romantic heartbreak back to back, with equal weight, where losing your girl was just as bad as the literal end of the world, and there was something both insane and magnetic about this gambit.


As Dylan enjoyed a second sold-out night at Café Yana on Saturday, less than a mile away, at the Donnelly Memorial Theater, the undisputed queen of folk music, Joan Baez, was performing. Since 1959, Baez had been at the forefront of the folk music revival in New England, helping to put Harvard Square on the folk music map (literally) with her performances at Club 47, followed by a series of increasingly popular recordings that showcased her uncanny ability to turn sometimes-obscure traditional songs into something vibrant and wholly contemporary. By November 1962, before Dylan could even score a proper gig in Boston, Baez’s image appeared on the cover of Time magazine.

Bob Dylan playfully climbs atop a car in Cambridge on a return visit in 1964, a year after he debuted in Boston at Café Yana and later joined friends for a Hootenanny at Club 47.Betsy Siggins

It was apparently just a coincidence that Dylan and Baez were both in Boston the same weekend. Baez, who grew up in Belmont and was uncomfortable with everything that came along with the fame she had achieved, had traded a Massachusetts address for one in California in 1961. Broadside treated her April 1963 return to the city as though she were visiting royalty: “There are not enough words and thanks to give her for giving us something beautiful and real; it is an honor to have Joan Baez with us again.”

“I didn’t want to meet her, but I knew I would,” Dylan wrote in his 2004 memoir, “Chronicles: Volume One.” “I was going in the same direction even though I was way in back of her at the moment.”

The pair had briefly crossed paths before: two 1961 encounters at Gerde’s in New York where Dylan seemed more interested in Joan’s sister, Mimi, than the folk star. Baez found him charismatic, but in each instance neither schedule, circumstance, nor hot pursuit from either party led to anything more. Dylan’s reported opinion of Baez before their collaboration was lukewarm if not outright dismissive, but this was about to change.

A Hootenanny, and an unforgettable after-party

Sunday nights at Club 47 were Hootenanny nights in which a rotating roster of musicians, with no headliner, would all perform a few songs each; rumors of both Baez and Dylan’s potential appearance had not only ensured a capacity audience but also a who’s who of local folkies onstage. In the book “Baby, Let Me Follow You Down: The Illustrated Story of the Cambridge Folk Years,” music producer Paul Rothchild recalled: “It just snowballed. Joan was there, Dylan, the Jug Band, [Ramblin’] Jack Elliott, [Jim] Rooney, The Charles River Valley Boys, Eric von Schmidt, [Bob] Neuwirth, Carolyn Hester. It was an incredible night. Nobody hogged the show.”

In the basement of Club 47, Betsy Siggins switched on the venue’s tape recorder and, upstairs, a microphone hanging from the ceiling captured the loose, celebratory showcase for the ages. While Siggins, a founding member and then employee of the club, has never made the tape public, snippets of it can be heard in the 2012 documentary “For the Love of the Music.”

While Eric von Schmidt, Ramblin’ Jack Elliott, and Dylan were performing together, Baez walked into the room. Von Schmidt recalled having trouble performing whenever he looked in her direction “such was her allure,” author David Hajdu reported in his book “Positively 4th Street.”

Joan Baez performs at Club 47 in Harvard Square in 1959. By 1962, she would be on the cover of Time magazine.Photo by Dick Waterman, courtesy of Betsy Siggins

Finally, at long last, Dylan got his solo moment at Club 47. As heard on the excerpts of the recording, von Schmidt introduces Dylan by saying he’s from New York. Dylan says he’s not from there, so von Schmidt offers that he’s from “some place in the Midwest.” Perhaps worrying that this introduction is getting too close to the actual truth of his Minnesota upbringing, Dylan offers “Boston,” to which von Schmidt replies, “Out in the midwest of Boston …West Roxbury,” nodding to their first adventure together and the drunken croquet game.

Dylan’s jokey introduction to his first song goes over like a lead balloon with the audience — Siggins described it as innocent and contrived, which is precisely correct — but as soon as his humor surfaces in one of his original songs, the crowd responds immediately and enthusiastically. That song, the first of his short solo set, undermines a long-held belief that “Talkin’ World War III Blues” was an April 24 studio improvisation unveiled after Dylan returned to New York to resume recording “Freewheelin’”; his performance of the complete song at Club 47 three days earlier indicates otherwise. It’s not unreasonable to wonder if he composed the song during his time in Boston that weekend.

But it was Dylan’s second and final solo song of the evening that would have long-lasting consequences. The brilliant “With God on Our Side” is a “finger-pointing song” — a term that he would use to label his most famous protest songs — which ends up pointing the finger right back at you, the listener, instead of some figure of authority. It’s an audacious composition that dares to ask why one might think the United States is a moral authority in the world. Even further, how can anyone believe that God chooses sides in a world that is filled with continual atrocities? It’s that rare political song that rises above current events to ask questions that can apply to any era, challenging the listener’s point of view in a way that’s fairly shocking the first time you hear it.

“When I heard him sing ‘With God on Our Side,’ I took him seriously,” Baez told writer David Hajdu. “I was bowled over. I never thought anything so powerful could come out of that little toad. When I heard that, it changed the way I thought of Bob. I realized he was more mature than I thought. He even looked a little better.”

At the close of the Hootenanny, no one wanted the good times to end, so an impromptu party assembled at 26 Surrey St., the Cambridge apartment of Sally Schoenfeld, Susie Campbell, and Joy Kimball (now Joy Overstreet) — all three were involved in the local folk music scene in various ways. “The apartment was just amazing,” Overstreet recalls. “Because it was over this market, there was no one to annoy with noise, so we just had parties all the time. This particular case was the biggest party we ever had.”

An apartment above a convenience store at 26 Surrey St. in Cambridge was the scene of a Club 47 after-party that included Bob Dylan, Joan Baez, and local folk luminaries on April 21, 1963.Courtesy of Joy Overstreet

A collage of photos from the party taken by Rick Stafford paints the scene: Baez holding court in the packed kitchen, Geoff Muldaur and Eric Von Schmidt jamming in the living room, Baez’s manager Manny Greenhill staring skeptically at Dylan as he takes a drag off a cigarette.

It was here at 26 Surrey St. that Baez and Dylan finally shared a room together for more than a passing moment. If Suze Rotolo had indeed been with Dylan in Boston at the beginning of the weekend, she wasn’t there by the time Sunday night rolled around. Perhaps she left on her own accord, perhaps Dylan encouraged it knowing that a meeting with Baez was imminent. According to accounts in “Positively 4th Street,” Baez found Dylan in one of the apartment’s bedrooms face to face with local Jug Band leader Jim Kweskin, singing songs together, but with a competitive edge that hadn’t been there in their prior encounters. Mark Spoelstra, a singer-songwriter who had dated Baez when they were teenagers, witnessed the musical confrontation: “They were singing there with their noses three inches apart, proving to each other how many lyrics they knew to all these songs or something. It was just ridiculous. It wasn’t fun. It was tense, and Joanie walked in on that. … She really seemed to enjoy watching that.” Spoelstra recalled Dylan eventually tossing his guitar down on the floor in the manner of spiking a football. In what was becoming a tradition, Dylan turned to Baez and asked, “Is your sister here?” Baez moved past the diss and into an actual conversation with the man she would later refer to as a “little toad.”

Eventually, Dylan showed off more of his original songs at the party, including “The Death of Emmett Till” — a song detailing the real-life horror of the lynching of a 14-year-old Black boy in Mississippi in 1955 — which arguably altered Baez’s career in that moment. “I was not ‘political’ at that time. When I heard ‘Emmett Till’ I was knocked out,” she explained in “Positively 4th Street.” “That song turned me into a political folksinger.” By the end of the song, the room had filled up with other partygoers, some stunned to see the hard-to-impress Baez under Dylan’s spell. “It was [as if] he was giving voice to the ideas I wanted to express but didn’t know how,” she said. Ironically, Dylan’s own political awakening came directly from his girlfriend, Rotolo, whose family’s commitment to civil rights, unions, and left-wing causes enlightened Dylan. Now, in turn, he was passing it along to Baez, who would, in more ways than one, soon replace Rotolo.

Departing after 2 a.m., Baez told Dylan he should visit her the next time she was in California. Their time together, as artistic collaborators and lovers, would be relatively brief but endlessly consequential. Mere months from the night at 26 Surrey St., Dylan and Baez would perform “When the Ship Comes In” together in front of the Washington Monument at the March on Washington. In the end, Baez would remain committed to causes of social justice throughout her career, while Dylan would completely transform again and again and again into different personas. Though they diverged artistically, their unwavering allegiances — for Baez, to one singular mission; for Dylan, to perpetual transformation — are deeply impressive and admirable in their own right.

In November 2021, at Dylan’s most recent performance in Boston, it became a stunning, humbling thought exercise to look upon the 80-year-old man enjoying an extended standing ovation at the Wang Theatre and comprehend that this was indeed the same scrawny kid, the “little toad,” who once struggled to get stage time in Massachusetts, right before everything changed.

Ryan H. Walsh is the author of “Astral Weeks: A Secret History of 1968″ and frontman for the band Hallelujah the Hills. Follow him on Twitter @JahHills.