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Bob Dylan once traded an Andy Warhol painting worth millions for a couch


Bob Dylan may have dipped his toes into the mad world of Andy Warhol’s Factory but he was never really a fully-fledged member of the scene, neglecting the pursuit of fame over pushing his own songwriting talent. Although being around the somewhat peculiar characters was an experience that Dylan wasn’t all too familiar with, it was also one that influenced his songwriting as he got a taste for a different life. With that said, there was one mistake he would make during this period which he would rue forever.

Dylan drifted in and out of the New York art scene throughout the mid-60s but never was at the forefront of it or got too heavily involved. The pinnacle of his involvement with the Warhol Factory crowd came when the bohemian singer-songwriter took part in one of pop artist’s infamous ‘screen tests’ in early 1965 when Dylan had strolled into Warhol’s studio and became his subject for a few brief moments. With two rolls of film lined up for a close-up and a wide shot, Warhol let the camera roll and captured Dylan.

Warhol biographers Tony Scherman and David Dalton, who created the book Pop: The Genius of Andy Warhol, wrote that “he [Warhol] was clearly star-struck, in awe of Dylan’s sudden, vast celebrity. He had a more practical agenda, too: to get Dylan to appear in a Warhol movie.”

Unfortunately, the movie with Dylan never came to fruition and the singer never became the Hollywood star that Warhol envisaged, largely because Dylan remained deliberately obtuse when in front of the limelight. As a thank you for appearing in the screen test, Warhol wanted to let Dylan know how grateful he was for him coming down and gave him a gift of a silver Elvis painting. Dylan accepted the soon-to-be-iconic painting in a typically nonchalant fashion, not quite aware of the worth of the treasure that Warhol had handed to him.

Dylan would later make one of the few missteps of his life when he decided to hand it to manager Albert Grossman in exchange for a couch. Yes, Bob Dylan swapped a painting worth millions and millions of dollars for a second-hand couch and that’s a decision he would grow to greatly regret. He later remarked about the misdemeanour to Spin in 1985 that “I always wanted to tell Andy what a stupid thing [I’d] done, and if he had another painting he would give me, I’d never do it again.”

During his time around The Factory, Dylan ventured on a rumoured romance with original ‘it’ girl Edie Sedgwick who he became friendly with which developed through a chance meeting through Warhol. She reportedly had an instant infatuation with the singer and, in reaction, it is rumoured that Dylan’s feelings were reciprocal. It is alleged the two of them had a secret whirlwind affair before Dylan married Sarah Lownds.

Her older brother, Jonathan, would even later claim that she became pregnant with Dylan’s child, but had to get an abortion due to her personal drug problems that she needed rehabilitation for, ultimately knowing she wasn’t ready to become a parent. It’s rumoured that not only ‘Like A Rolling Stone’ but also, ‘Leopard-Skin Pill-Box Hat’ and ‘Just Like a Woman’ were all written with Sedgwick in mind.

Even if Bob Dylan’s time at The Factory would see him miss out on this iconic piece of Warhol art in the end, overall it was an experience that was a positive one from a personal and artistic perspective. If it is true that ‘Like a Rolling Stone’, ‘Leopard-Skin Pill-Box Hat’ and ‘Just Like a Woman’ were written thanks to an encounter which involved Warhol then it’s fair to say Dylan has scraped back a dime or two from the millions he accidentally swapped for a couch.