The Story Of Bob Dylan’s Worst Trade Deal

In the vibrant years of 1964 to 1966, Andy Warhol, along with his assistant Gerard Malanga, created 472 short portraits at the famed Factory in New York, featuring an array of individuals, from the famous to the peculiar. Among these subjects was none other than Bob Dylan.

Ironically dubbed Screen Tests, Malanga humorously emphasized that these weren’t auditions for a film but rather a playful “Hollywood parody.” Despite Dylan’s reputed lack of affinity for plastic arts, he acknowledged in a 1985 interview with Spin magazine that he once made an intriguing trade deal with Warhol.

According to the tale, Dylan sold a Warhol painting, specifically one of Elvis Presley, with a tongue-in-cheek admission that he did it to acquire a sofa. Reflecting on this unconventional barter, Dylan expressed a desire to convey to Warhol the perceived folly of the transaction, half expecting another painting in return.

The encounter resulted in Dylan trading an Elvis Presley artwork he wasn’t particularly fond of for a sofa, marking a whimsical chapter in the interaction of these two towering egos. Despite the encounter, it appears the artistic exchange fell short of a genuine creative connection, as Warhol’s portraits aimed to capture souls with his Bolex, yet failed to spark a profound collaboration between these iconic figures.