I just re-read Frank Sinatra’s Playboy Interview from ’63, you should too…


The first time I read this interview, I was about 10 years old. Back when we were living in the South side of Chicago in a Bridgeport bungalow. Whenever opportunity and privacy would arise, I used to stealthily rummage through my dad’s Playboy collection. His collection went way back. He cleverly kept it stashed in the basement’s backroom, behind a large box full of boring papers. As if that would deter my prying eyes.

Anyway, while I was of course mesmerized by the pictures and nudity, I found myself getting more and more drawn into the writing as I went through the issues. While I found many of the articles and short stories to be interesting,  I never quite got into the interviews. This was one of the few, however, that sucked me right in.

Maybe it had to do with the fact that my dad had Sinatra playing on the basement’s hifi virtually every evening, while enjoying his evening whiskey in his La-z-boy after a hard day at his gas station. His love of Sinatra and the standards always seemed to clash with my love for pop and rock n’roll, but I always kept a hidden appreciation for it. Dare I say, I turned into quite a fan of Frank Sinatra, all the Big Bands, Count Basie and even Bobby Darin later in life. Thanks to my early exposure to Pop’s collection of the greats.   

So naturally, I was drawn into the piece about Sinatra, when I finally came across this particular issue from 1963. Which incidentally, was a year before I was born. Here is an interesting thing I’d noticed as I read through the back issues. Pop didn’t keep every one that came out in a given year. Some years, he would have all of its respective issues (he subscribed religiously). Yet in some other years, there would be as few as 4 or 5. It eventually became clear to me that he only held on to the ones he considered to be “keepers”. 

The Sinatra issue was definitely one of those. 

I remember on my first go-round, most of what was said just flew clear over my head. Yet, I remember being impressed by his slick command of the language. Before then, I hadn’t actually ever imagined that the man had such a vocabulary on him. He just never quite came across that way when I saw him on TV or the occasional movie. I remember saying to myself, “wow, he’s a pretty smart guy”. 

For the first time in about 40 years, I sat down and read that interview again via this Longform post, as well as the ebook (which is great, I highly recommend it).

Suffice to say, I’m very glad I did. I now have an even greater appreciation for his humanism, his compassion and his empathy. His worldview was both insightful and loaded with foresight. It was obvious he was well-read and able to form very complex opinions about very complex topics. 

This is a guy who despite his own incredible success, never forgot about the struggles of everyday people and even minorities. He expressed himself to be a true progressive and activist, despite acknowledging his own limitations as being “just a singer”. Though I have always had nothing but respect for the man and his contribution to the world of music and popular culture, I now possess an even greater respect for him now as a person as if that is even possible. He clearly shows himself, warts and all. To be a flawed, often arrogant, yet incredibly caring and giving person. Something the world needed more of then as much, if not more so, as it does now. 

It makes me want to be better too.  – T

Playboy Interview: Frank Sinatra

This interview is part of The Playboy Interview: Music Men, a new ebook anthology that also includes conversations with Ray Charles, Kanye West, Elton John, and more. Buy it today at Amazon.Playboy: Frank, in the 20 years since you left the Tommy Dorsey band to make your name as a solo singer, you’ve deepened and diversified your talents with a variety of concurrent careers in related fields. But so far none of these aptitudes and activities has succeeded in eclipsing your gifts as a popular vocalist. So why don’t we begin by examining Sinatra, the singer?

Sinatra: OK, deal.

Playboy: Many explanations have been offered for your unique ability—apart from the subtleties of style and vocal equipment—to communicate the mood of a song to an audience. How would you define it?

Sinatra: I think it’s because I get an audience involved, personally involved in a song—because I’m involved myself. It’s not something I do deliberately: I can’t help myself. If the song is a lament at the loss of love, I get an ache in my gut. I feel the loss myself and I cry out the loneliness, the hurt and the pain that I feel.

Playboy: Doesn’t any good vocalist “feel” a song? Is there such a difference.…

Sinatra: I don’t know what other singers feel when they articulate lyrics, but being an 18-karat manic-depressive and having lived a life of violent emotional contradictions, I have an overacute capacity for sadness as well as elation. I know what the cat who wrote the song is trying to say. I’ve been there—and back. I guess the audience feels it along with me. They can’t help it. Sentimentality, after all, is an emotion common to all humanity.

Playboy: Of the thousands of words which have been written about you on this subject, do you recall any which have accurately described this ability?

Sinatra: Most of what has been written about me is one big blur, but I do remember being described in one simple word that I agree with. It was in a piece that tore me apart for my personal behavior, but the writer said that when the music began and I started to sing, I was “honest.” That says it as I feel it. Whatever else has been said about me personally is unimportant. When I sing, I believe. I’m honest. If you want to get an audience with you, there’s only one way. You have to reach out to them with total honesty and humility. This isn’t a grandstand play on my part; I’ve discovered—and you can see it in other entertainers—when they don’t reach out to the audience, nothing happens. You can be the most artistically perfect performer in the world, but an audience is like a broad—if you’re indifferent, endsville. That goes for any kind of human contact: a politician on television, an actor in the movies, or a guy and a gal. That’s as true in life as it is in art.

Playboy: From what you’ve said, it seems that we’ll have to learn something of what makes you tick as a man in order to understand what motivates you as an entertainer. Would it be all right with you if we attempt to do just that—by exploring a few of the fundamental beliefs which move and shape your life?

Sinatra: Look, pal, is this going to be an ocean cruise or a quick sail around the harbor? Like you, I think, I feel, I wonder. I know some things, I believe in a thousand things, and I’m curious about a million more. Be more specific.

Playboy: All right, let’s start with the most basic question there is: Are you a religious man? Do you believe in God?

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