Bob Dylan is an intellectual. The songs he wrote in the 1960s poetically represented his entire generation and many of those to follow. But when he wasn’t writing music, Dylan would spend a lot of time playing chess.
There was a chess club in New Jersey where Bob Dylan would play chess and perform his music. According to Dylan’s manager Victor Maymudes, they would play one another in chess.
Plus, the band would also play one another while touring in 1974, between shows.
Bob Dylan, The Chess Psyche Out Technique
Similar to poker, Bob Dylan would play the opponent rather than the game. In a match, he would talk a great deal to psyche out his opponent. He would also nervously shake his leg, possibly as another unique distraction.
In one particularly unusual occasion, the Gaslight Café in New York City couldn’t afford to pay Bob Dylan for his performance, so they paid him in chess pieces. “We’re too poor to pay you,” said the owner. “We’ll have to give you chess pieces.”
That night, he exchanged the pieces for food and got a few drinks for the pieces.