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What happened when Bob Dylan met Frank Sinatra

Bob Dylan has nothing but positive memories about Frank Sinatra. In 2015, for example, he paid tribute to Ol’ Blue Eyes by covering a selection of his beloved tracks, and when the two met, it transpired Sinatra was a fan of his work, too.

Although the two now-iconic figures of contemporary rose to fame in different eras, and sonically their output shared little resemblance, their cultural importance made them the voice of their respective generations. Both Dylan and Sinatra endured a zeitgeist appeal and represented similar sensibilities to their legions of fans. Nobody was more conscious of their likeness than the blue-eyed pair themselves.

When Dylan decided to revive the songs of Sinatra for the tribute album Shadows in the Night, the singer explained his unselfish reasoning for doing so. “I don’t see myself as covering these songs in any way,” he said. “They’ve been covered enough. Buried, as a matter a fact. What me and my band are basically doing is uncovering them. Lifting them out of the grave and bringing them into the light of day”.

Dylan’s love of Sinatra has been a fixture throughout his life. Even in his early days, when he was a rebellious troubadour, ‘Ol Blue Eyes covers were common in his set. He also dotingly described him as “the mountain” of music. “When you start doing these songs, Frank’s got to be on your mind,” he told The Guardian during the ’60s. “Because he is the mountain. That’s the mountain you have to climb, even if you only get part of the way there.”

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When they first met, immediately, the duo felt they were kindred spirits. They had bundles of arrogant energy in common and had an air of superiority over their rivals which helped gel their relationship. While Dylan later remembered the event, details on the intricacies of the meeting were a little hazy, apart from one comment which Sinatra made, which struck a chord with him. “He was funny, we were standing out on his patio at night and he said to me, ‘You and me, pal, we got blue eyes, we’re from up there,’ and he pointed to the stars,” Dylan remarked. “These other bums are from down here.’ I remember thinking that he might be right.”

Years later, the two would reunite shortly for a televised tribute to Sinatra to celebrate his 80th birthday in style, which would turn out to be one of his final public appearances before his death. Dylan headlined the concert alongside names as illustrious as Bruce Springsteen and Ray Charles. 

Interestingly, he opted to perform one of his more obscure tracks, ‘Restless Farewell’, which initially appeared on The Times They Are a-Changin’ in 1964. Many speculated that Sinatra ordered him to play it as it was his personal favourite. However, Dylan has never confirmed this theory. Despite their music catalogues lying miles away from each one another, it was a different story for them as people. Dylan and Sinatra forged an unlikely bond that bridged two generations of America.