What Did Sinatra and Dylan Talk About?

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Frank Sinatra Bob Dylan

I don’t know about you, but I’ve always wondered what kind of conversations Frank Sinatra and Bob Dylan had. Knowing that they hung out at least once at Sinatra’s pad around the time of Frank’s 80th birthday bash (although according to Frank Jr. they communicated on multiple occasions), and being as inexpressibly devoted a fan as I am of both artists, I couldn’t help but wonder what kind of words passed between them, and I have dreamed of one day obtaining the bootleg tapes.

Today, thanks to Dylan’s wonderful new interview with the estimable Bill Flanagan, we have been treated to one excerpt of their dialogue, and maybe it’s all we truly need and deserve.

Bob Dylan says, of being with Frank Sinatra:

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. “These other bums are from down here.” I remember thinking that he might be right.


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