Bob Dylan also maintained his cool when he sat for his Screen Test portrait in late 1965 or early 1966—stone-faced in his dark sunglasses, scratching his nose and looking unfazed. When he got up to leave, the acerbic musician decided to help himself to Warhol’s silkscreen print of Elvis dressed as a cowboy: “I think I’ll just take this for payment, man.” Robert Heide recalled, “Andy’s face turned tomato-soup red, because Andy would promise people things, and he wouldn’t necessarily deliver. He wasn’t expecting Dylan to do that.” The friction between the two camps was partially rooted in the cult of authenticity that surrounded Dylan, a sensibility that clashed with Warhol’s unapologetic embrace of artifice and commercial culture. The musician’s involvement with Sedgwick (the likely subject of his songs “Just Like a Woman” and “Leopard-Skin Pill-Box Hat”) also exacerbated tensions. Dylan and his manager, Albert Grossman, hoped to turn Sedgwick into a film ingénue and encouraged her to break with Warhol, which she did. “If you get to the emotional truth of the thing, Andy and Edie loved each other,” Bibbe Hansen said. “Just like when two people are very, very fond of each other and something happens and people get in the way and they get riled up, the split is that much bigger.”

From Chapter 11 of The Downtown Pop Underground — order online, or from a local independent bookstore