Out in paperback this month, David Hajdu’s Positively 4th Street: The Lives and Times of Joan Baez, Bob Dylan, Mimi Baez Farina and Richard Farina (North Point Press) is part biography, part popular music history and part Greenwich Village travelogue, circa 1962.

It’s obvious why a writer of Hajdu’s expertise—his last book was on jazz vocalist Billy Strayhorn—would want to have a go at Dylan and the elder Baez sister. They were folk/rock royalty, the couple everyone talked about—they were Britney and Justin with talent.

But why would Hajdu devote so much time and energy to documenting the lives of Joan’s little sister and her husband Richard? As Hajdu points out in his richly-reported book, Mimi was, in some ways, a greater talent than her better-known sibling. A preternatural beauty and a widow by the time she was 21, hers is an irresistible story. And Farina, well, he was a storyteller, a musician and a writer of such skill that his only novel made a jealous man of close friend Thomas Pynchon. "Holy shit man," Pynchon, the most inventive novelist of his era, wrote after reading the manuscript that became Farina’s only novel, Been Down So Long It Looks Like Up to Me. "How would ‘holy shit’ look on the book jacket? What I mean is you have written, really and truly, a great out-of-fucking sight book."

Hajdu recently spent six months with Wynton Marsalis for an upcoming piece in Atlantic Monthly and has begun writing a book about mid-century comics. He is on tour again this month to support the Dylan-Baez-Farina paperback, but he took time out recently to talk about the book, the four characters at its heart and how he managed to get in touch with the famously reclusive Pynchon.

Gadfly: For pretty obvious reasons, a lot of other writers have focused exclusively on Joan Baez and Dylan. Why did you decide to focus on all four of these people?

Hajdu: There are a number of reasons. I was interested in the Farinas as a point of contrast. By telling the story of all four of them you start with four people who might seem to have the same kind of potential. You have two sisters who are both musically gifted. Practically everyone who knew them both—including Joan—thought that Mimi was the superior musician, as a guitarist. Joan had a better voice, and Joan had something else—but the similar genetic makeup. So the two of them are a case study in what it takes to succeed in this culture, and also of the role of sibling relations in the development of artistic lives.

And then Dylan and Farina are similar points of contrast. Dylan's detractors—I'm not among them—have often painted him as an overly ambitious young man who used everything he came in touch with to his benefit. But much more than that accounts for Dylan's success as an artist and as a cultural figure. Richard Farina was much more ambitious. Richard Farina was infinitely more ambitious. So what if you have two people, one who has great ideas—Richard Farina—and ambition on a monstrous scale and then someone who also has great ideas [Dylan] but a different kind of talent, and a deeper talent? And then the relationships between all four of them were intertwined. So it’s more than just the effect of sibling relationships on careers, but also fraternal relationships. The four of them are an irresistible study; it was a little laboratory for me.

You explain how Joan Baez enjoyed more early success than almost anyone in the folk scene, including Dylan. What effect did her popularity have on other artists and the scene as a whole?

It's immeasurable, it's absolutely immeasurable. Joan was the first young star in the folk milieu. She made a music that had different associations, she made it cool and young and hip and she helped a whole generation connect with the music, connect to folk music in a way that was related to their identity and their concerns. You had people seeking an individual generational identity in the shadow of the World War II generation, in the shadow of a generation that won The War, seemed to rule the world and was infusing everything in the culture with a kind of bombast and power—the confidence and the kind of overt the top rah-rah Americanism. Big cars, jets, confidence in anything that was American, mass-produced, commercial. Folk music was played by older people and had been around forever. It was folk music for goodness sakes. Young people were able to see that as an antidote to everything their parents represented. For once they had someone their own age to connect to. Joan was really the Elvis figure, not Bob.

You alluded to this before, I think. Like a lot of artists who came after him, Dylan sort of reinvented himself on a few occasions, didn't he?

Yeah, he sure did. But so did I. I don't know about you. That's kind of the nature of what it means to be American. It's part of the American ideal, it's part of the great promise of this country. It's a New World so you can become a new person here; I think I used a line like that in the book. And especially in show business, there's a long tradition that predates America of reinvention in show business. But the irony of it in the case of Dylan and his peers and Joan, too, was that they performed their roles and adopted false personas in the nature of authenticity. That's really the irony of it. On the surface they were challenging the artificiality of their parents‘ generation, they were challenging the Vegasy artificiality of Vic Damone and that whole ilk of singers. But what they were doing was certainly just as much a pose—but in the name of authenticity. It’s really very peculiar and complicated.

Dylan's first record was almost never released, you say, and when it finally was it sold pretty poorly, didn't it?

I don't have the numbers in front of me, but it was a disappointment. John Hammond, who had signed him, was under tremendous pressure to drop him. In the halls of Columbia Dylan was derided as Hammond’s folly. And the record is quite good, but it’s not the Bob Dylan we know now. He hadn't yet found his voice, certainly as a composer. And it's a remarkable act of prescience on Hammond's part that he signed this guy at all. He certainly didn't see any songwriting genius in Dylan at that point. He hadn't written works of genius yet, he had only written a handful of things of any merit. But then Dylan started composing and [1963’s The Freewheelin' Bob Dylan] seems like some kind of miracle following the first album. The rate of his growth was just breathtaking. In a matter of months he was on another level, from one album to another album to another album. He just seems to be almost a different artist. It's the same kind of growth that you could see in the Beatles just a few years later. There's practically no precedent for it in the music of subsequent generations.

Dylan and Joan Baez tapped into sort of a cultural moment as much as a musical movement. How were they able to pull that off?

It was kind of remarkable. It was this odd time when it was a trend, it was chic to be serious, introspective, poetic, socially conscious, to apply self-sacrifice to social causes. Why? The peak of the Civil Rights movement, the Vietnam War was just catching fire, beginning to become a controversy in this country. The Cold War was at a peak. I was a kid in those days, and I remember being in school with crayons and having to draw pictures of how we would design our fallout shelters. And that was a class assignment. [Dylan and Baez] gave voice to those concerns through a music that seemed appropriately serious and had the right kind of gravitas.

You talk about the legend surrounding Dylan's going electric at the Newport Folk in '65. That's sort taken on mythic status over the years and it's become overblown to a certain extent, hasn't it?

Well, it definitely has. I read the contemporary reports, and it was not seen as a cataclysm at the time. It was absolutely impossible that most of those people were surprised to hear Bob Dylan playing with a rock band. "Like a Rolling Stone" was on the pop charts. You couldn't drive to Newport without hearing "Like a Rolling Stone" the whole ride. Bringing it All Back Home had come out something like six months before that. "Like a Rolling Stone" was his second rock and roll single/ folk rock single. So there's no way that everyone was shocked. They might’ve been shocked if he came out with a folk guitar—that would’ve been a shock.

Now there were some complaints about the performance that day. But they didn't dominate the audience reaction. The nature of those complaints is up for debate. Maybe it was the sound system. The Newport Folk Festival wasn't wired for a rock band. The sound system wasn't set up for that kind of performance, and surely some of the diehard old-line folk purists did object to the commercialism that they associated with rock n roll. It was popular music, my God. Folk music can’t be popular. The moment has been reinvented over the years because it serves a handy function. Every generation needs not just great music and great artists, we need great moments. We just need them and that became one of them.

Thomas Pynchon was Farina's best man, as you note, and you quote Pynchon several times in the book. How were able to pin him down?

He was very generous with me and helpful and I think that was out of respect for his old friend Richard. He responded well to my questions, by fax, by way of an intermediary. One day I came home and the fax machine is churning and it was answers from Thomas Pynchon. I was so excited about it. He had never done this before. I couldn't sit still. I had to go out and take my dog for a walk, just kind of run around the block. My mouth was parched so I put the dog on a post and I ran in to get a cold drink at the deli. I came back to the house, pacing, the buzzer rings, it's the police. I had left my dog tied to a post. Could I say I'm sorry, officer, I just got a fax from Thomas Pynchon? I'm sure he’d understand.

Farina’s novel is still in print but you say near the end of the book that he never started his second one, and you explain how it was going to be a memoir of his times with Dylan and the Baez sisters. Did you in a way write the book that he never got a chance to?

That was not my intent. I had put a couple of years of work into the book and done probably half the interviews when I found that out from his editor. I was surprised but it just seemed like a poetic convergence, so I loved hearing that fact. But I didn't set out to write the lost Richard Farina novel. I did have that fact in mind when I asked [artist] Eric von Schmidt to do the cover. It was a painting inspired by a poster that he made for a concert that Joan and Bob did. He repainted it and added Richard and Mimi in the back. I had that in mind because he had only ever done two book jackets before (Farina’s novel and a collection of his previously unpublished work). So no I didn’t set out to write the lost Richard Farina book, but I found a lot of pleasure in the convergence.