Bob Dylan's Dumbest Move Ever, By a Mile

In 1966, the singer traded a Warhol for a sofa. Estimated price today: $50-75 million

Barbara Rubin was a complex individual. While still in her teens, she directed a celebrated—more accurately, notorious—film entitled Cocks and Cunts; she was a close colleague of Jonas Mekas, the dean of New York’s avant-garde filmmakers, and that’s her mussing Bob Dylan’s hair on the back of Dylan’s 1965 album Bringing It All Back Home.

Rubin, as I wrote in POP, my 2009 Andy Warhol biography, “was a groupie with a cultural agenda.”¹ Rubin’s sometime boyfriend Allen Ginsberg (yes, Ginsberg swung both ways) called her a “visionary.” As Ginsberg told an interviewer, Rubin considered himself, Dylan, Warhol, and the Beatles “heroes of a cultural revolution involving sex, drugs, and art” (she wasn’t far off), whom she considered it her job to put in touch with each other.² Whatever her accomplishments—one critic called Cocks and Cunts (which she was persuaded to rename Christmas on Earth) "an essential document of queer and feminist cinema”—Rubin was not much more than one of her day’s countless self-appointed seers with a nutty agenda. The difference was that she had access to the goods.³

The omnipresent, semilegendary Barbara Rubin and preoccupied friend (see above paragraph)

Dylan and Warhol, for instance, not to mention mere demigods such as Lou Reed (Rubin brought the Velvet Underground to Warhol’s attention). She was a habitué of Warhol’s studio, the Factory, at 231 East 47th Street, an abandoned remnant of the neigborhood’s light-industry days (it had been a hat manufacturer’s). Warhol never bothered to replace its creaky elevator, whose gated door took repeated shoves to open, nor its payphone. The Factory’s signature piece of furniture was a badly sagging couch that Billy Linich, Warhol’s ex-lover and chief factotum, had lugged in off the street. One Factory regular complained that he’d gotten crabs from it. Billy responded, huffily, “I was never aware of anyone getting crabs from it. If they did, it was after it had been used in movies where people were screwing on it.” (Billy was referring to Warhol’s 1964 film Couch, in which Warhol’s chief assistant, Gerard Malanga, anally penetrates a young woman, the film’s most sexually explicit scene, but not by all that much.)

Barbara Rubin’s most notable matchmaking coup came one day, probably in January, 1966, when Bob Dylan, his consigliere Bob Neuwirth and his road manager, Victor Maymudes, parked Dylan’s station wagon across 47th Street from the Factory and rode the nasty elevator upstairs.