When Frank Sinatra Met Bob Dylan

The music legend, at 75, opens up about modern music, his latest album — and his startling encounter with 'Ol' Blue Eyes'

by Zachary Leeman | Updated 27 Mar 2017 at 7:43 AM

“In my 20s and 30s I hadn’t been anywhere,” said 75-year-old Bob Dylan in a recent and rare interview that was posted exclusively to his website. “When I was young, there were a lot of signs along the way that I couldn’t interpret. They were there and I saw them, but they were mystifying. Now when I look back, I can see them for what they were, what they meant. I didn’t understand that then, but I do now.”

It’s an odd confession from a man who had more insight into the human condition in his 20s than most have at his age now. After all, Dylan was only a 20-something-year-old man who “hadn’t been anywhere” when he recorded such classics as “Blowin’ in the Wind,” “The Times They Are a-Changin,” and “Like a Rolling Stone.”

In this new wide-ranging interview with Bill Flanagan — meant to promote the March 31 release of Dylan’s triple record called “Triplicate” — the musician spoke of modern music, his continuing growth as an artist, and the recent losses of so many legendary artists he considered friends.

On the recent deaths of people like Merle Haggard, Leonard Cohen, and Leon Russell, Dylan was blunt about aging and about losing artistic colleagues. “We were like brothers, we lived on the same street and they all left empty spaces where they used to stand. It’s lonesome without them.”

Related: Bob Dylan, in Absentia, Awarded His Nobel

But perhaps the most interesting story to come out of the insightful 8,000-word interview was Dylan’s comments about meeting fellow musician Frank Sinatra.

“I think he knew ‘The Times They Are a-Changin’ and ‘Blowin’ In the Wind.’ I know he liked ‘Forever Young,’ he told me that. 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,” said Dylan, who also said he only saw the great Sinatra “maybe once after that.”

Dylan also revealed that he and former Beatle George Harrison were once set to record with Elvis Presley — but it never came to pass. "He did show up, it was us that didn't," he said without elaborating on what could have been a potentially historic music session.

Dylan's history of rubbing shoulders with some of history's biggest and most iconic artists didn't end there. The folk singer also told of the time he met actor John Wayne.

"I met him on a battleship in Hawaii where he was filming a movie, he and Burgess Meredith. One of my former girlfriends was in the movie, too, and she told me to come over there; she introduced me to him and he asked me to play some folk songs. I played him 'Buffalo Skinners,' 'Raggle Taggle Gypsy,' and I think 'I'm a Rambler, I'm a Gambler.' He told me if I wanted to I could stick around and be in the movie. He was friendly to me."

Dylan continued his revelations by touching on modern music and the feeling rock 'n' roll once gave the world. "Modern music and songs are so institutionalized that you don't realize it," he said.

On rock and the power of music, Dylan gave an eloquent lesson many musicians today would be wise to note. "It was skeleton music, came out of the darkness and rode in on the atom bomb and the artists were star headed like mystical Gods. Rhythm and blues, country and western, bluegrass and gospel were always there — but it was compartmentalized — it was great but it wasn't dangerous. Rock and roll was a dangerous weapon, chrome plated, it exploded like the speed of light, it reflected the times, especially the presence of the atomic bomb, which had preceded it by several years. Back then people feared the end of time," said Dylan.

Related: Bob Dylan, Forever Young, Turns 75

He continued, "Rock and roll made you oblivious to the fear, busted down the barriers that race and religion, ideologies put up. We lived under a death cloud; the air was radioactive. There was no tomorrow, any day it could all be over, life was cheap. That was the feeling at the time and I'm not exaggerating."

"Rock and roll made you oblivious to the fear."

Bob Dylan rarely grants interviews or answers questions about his life and career — and when he does, it's easy to forget what a great influencer he is. The artist is modest and quick to speak of other people's accomplishments well before his own significant body of work.

"If somebody does achieve greatness it's only for a minute and anyone is capable of that. Greatness is beyond your control — I think you get it by chance, but it's only for a short time," said Dylan.

If that's true, the musician who has had songs and lyrics transcend time and who still manages to dazzle crowds from a stage may be the exception to the rule.

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