Dylan and Sinatra



This one is incredible.

“Happy Birthday, Mr. Frank”, Bob Dylan says to Sinatra on the occasion of the older man’s 80th birthday.

At a star-studded evening superstars like Little Richard, Bruce Springsteen, Ray Charles, Tony Bennett and Bono came to serenade the great one with a selection of the songs that he made famous. Dylan was supposed to play “That’s Life”, which might have been great, but when he got there, the story goes, Sinatra himself requested “Restless Farewell”, the closing track from The Times The Are A-Changin’. Dylan had never performed this song in concert before (the only other known performance of it other than the album take was on the Canadian TV show Quest thirty-two years earlier). Backed by his touring band and a string quartet, Dylan absolutely crushes this one. It’s a beautiful version, and the only non-Sinatra song performed that night. Watch it here.

Dylan has a persona that seems like it could hardly be more removed from that of Sinatra. They are polar opposites in so many important ways: voice, repertoire, compositionally. The quarter century that separates them in age seems particularly enormous given the rapid transformation of popular music in the 1960s. Nonetheless, Dylan is clearly a fan. So much of Sinatra’s appeal lies not in his voice, but in his phrasing, and so too with Dylan. When Dylan released a Sinatra cover on his website earlier this year (rumoured to be a tease for his new album), some people were surprised, but they need not be. Dylan grew up listening to an enormous range of music, and Sinatra was obviously a key part of that. Bjorner notes that only four singers were invited by Sinatra to his house after the show: Stever Lawrence, Eydie Gorme, Springsteen and Dylan. What a group that must have been.

At the end of the show, the entire ensemble sang “New York, New York”, with Sinatra joining for the final few notes. It was his last performance on stage, and he passed away a few years later in 1998. I’ve always been fascinated by Sinatra, and I find him all the more fascinating for the fact that of all the singers in the world to request a song from, he’d choose Dylan, and of all the songs, he’d choose one of the most obscure of his entire oeuvre. But, after all, the final phrase:

So I’ll make my stand

And remain as I am

And bid farewell and not give a damn

is probably as close as folk ever came to “My Way”.

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