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James Kaplan’s Sinatra: The Chairman completes his two-volume biography (Frank: The Voice was volume one) of the man widely regarded as the great interpreter of American popular song. While Sinatra has already inspired a library of books, no one else has succeeded as well as Kaplan in teasing out the complicated relationship between the singer’s life and art. Reached by phone in New York, Kaplan was happy to discuss the results of his ten-year effort to document a public life that stretched across more than six decades. This interview has been lightly edited for length and clarity.

RA: Reading Sinatra: The Chairman, a quote of Joni Mitchell’s about David Geffen kept springing into my head, which is: “He’d have to spend a lot less time being generous if he spent a little being fair.” Maybe in Sinatra’s case, the word “fair” should be changed to “sensitive to other people,” or “reasonable.” I don’t know what word you want to put there, but could you explain the relationship between his incredibly legendary generosity and the sort of difficulty he could have in treating people around him well?

JK: Sure. I think that deep down he was a helpless narcissist, conditioned into that state by a brutally inconsistent mother. He always said he didn’t know whether she was going to hug him or hit him, and that was literally true. She hit him. She pushed him down a flight of stairs when he was a kid. She once pushed him under the surf down at the Jersey shore. And then there were the times she would pamper him. She was frequently absent, and this taught him not to trust human relationships.

I think that a lot of his generosity stemmed from a sort of abiding, overwhelming sense of guilt that permeated him. A lot of it also stemmed from grandiosity, from this sense of himself — as Gay Talese put it in his great article “Frank Sinatra Has a Cold” — as padrone, or godfather, this honorific from the hill towns of Sicily. The padrone takes care of everybody in the village, and that was Sinatra.

But when it came to human relationships, he found them a mathematical equation too complex for him to invest time in trying to solve. His own daughter Tina wrote in her very affecting memoir My Father’s Daughter, “My father was a deeply feeling man who was unable to attain an intimate relationship with another human being,” and one can only infer that this remark was autobiographical to a certain extent. She was talking about his inability to settle down — to find a true love — but I think it also applied, as close as they were, to his first wife and to his daughter. This is leaving out the problematic question of his son. He was usually absent, just as his own mother had been, and when he was present, he was always about to go. I think Nancy Sinatra wrote someplace that her father was always leaving, and always was. He was pathologically impatient, always bound and determined to be onto the next thing.

RA: Since you mentioned Junior, let’s talk about Junior for a moment. I’ve actually interviewed Junior a couple times, and I’ve honestly —

JK: Oh, boy.

RA: He was a difficult interview only in the sense I had a ridiculously hard time getting him to say anything about his dad. In fact, if I remember right, he didn’t even use the word “dad.”

JK: No, no. He calls him Frank Sinatra. And he has said a number of times in his own concerts, “I am now going to devote five minutes to the music of Frank Sinatra because that is exactly how long Frank Sinatra devoted to me.”

RA: Oh, wow. I interviewed him right before he did a concert with Bill Miller on piano — you know, “Sinatra Sings Sinatra.” So it was a different occasion, but he was still very reluctant to talk about his dad. I had three or four interviews with him, and I don’t think I ever got a solid quote about his dad beyond the boilerplate stuff — the obvious.

JK: It was a tortured relationship. Sinatra’s relationship with his own father was nearly nonexistent, and so unfortunately that passed along to his relationship with his son. Girls were easier for him. But Junior was difficult from the word “go.” We should also emphasize that Frank Sinatra, Jr. was not his birth name. He was named Franklin Wayne Emmanuel Sinatra, and he began calling himself Frank Sinatra, Jr. — either it was his own idea or on the advice of somebody — when he began his own singing career. It is a ludicrous understatement to say that he had big shoes to fill, and there was a deep shadow over him. It was an impossible situation to be in. To be the son of Frank Sinatra and to try to sing and to call himself Frank Sinatra, Jr. was, one can only say charitably and politely, somewhat destructive.

RA: Did you get to talk to Junior, by the way?

JK: I was talked to by Junior. When I began my work, I was obliged to approach the family. I wrote to each of them: never heard from Nancy, Tina turned me down through her lawyer, Robert Finkelstein. This changed somewhat when I began my second volume, but that’s another story. They never cooperated with me, but very early in my work for the first book, my phone rang one afternoon and I pick up and it is Junior on the line. He proceeds to ream me out for 20 minutes saying over and over again that he has absolutely no intention of ever speaking to me for my book. And I just kept thinking, well, why’d you call? But it was a fascinating experience. The voice is —

RA: Remarkably like his dad’s.

JK: Exactly! But dead inside.

RA: Yeah! When you see him sing on stage, “Sinatra sings Sinatra,” it’s incredible. It’s like Frank Sinatra’s voice, but the wind’s been let out of the balloon. The soul is missing, but the identical voice.

JK: It is sad, and it’s a metaphor for the whole thing: for who he is, for the relationship.

RA: But he devoted a significant number of years of his life to being his dad’s band leader at the end.

JK: He did. And he took a lot of — I was about to say shit, but however you want to put it — abuse from Frank Sinatra on the bandstand. It was at best a collegial relationship, and, at worst, which it frequently was, testy and abusive on Senior’s part. Frank, Sr. was aging, his powers were waning, he was taking too many different medications (not mixed intelligently), and the results were often rough. He was forgetting lyrics, he collapsed a couple of times on stage, and it was King Lear-like. He was an old man lashing out, and his son was an easy target.

RA: It’s funny — reading your book, I thought of King Lear too, but in relation to Don Rickles, who seemed to have the fool’s permission to say the stuff no one else could to Sinatra and got away with it. How did that happen? How did Rickles get to say stuff that literally no one else would have been able to say to Frank Sinatra?

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Sinatra: The Chairman by James Kaplan

IN_ABOWITZ_SINATRA_CO_002 Frank: The Voice by James Kaplan

JK: Well, I think that it’s natural for a potentate to have a fool. Sinatra walked into that little nightclub — Slate Brothers on La Cienega in Los Angeles — in the mid-‘50s. Don Rickles only happened to be at Slate Brothers because Lenny Bruce had gotten fired for saying some pretty vile things on stage. He used the word “cocksucker” on stage and he might as well have set off a hand grenade.

At the 11th hour they needed a sub and they called in Rickles. Rickles came in and that night and — just pure kismet — Sinatra and his entourage happened to stop by. Maybe they were expecting to see Lenny Bruce. The moment Sinatra walks in, Rickles says, “Make yourself comfortable, Frank, hit somebody.” There is a silence, and you can count one, two, three, four, while all the thick-necked guys around Sinatra look at the leader to see what his reaction’s going to be. And then suddenly Sinatra smiles. He just starts guffawing, and of course all his entourage is tremendously relieved and they all start guffawing too, and that’s the beginning of it. Rickles is a kind of genius, and Sinatra was always deeply sensitive to skill and brilliance wherever he saw it — his musicians, his arrangers, his conductors — and he recognized that Rickles was not just some schmo who was trying to score off Sinatra. The kid had something.

RA: In The Chairman, near the end of his life during one of his final performances, you have Rickles yelling as Sinatra heads towards the stage, “Remember: they’re clapping out of pity,” or something like that. I mean, it’s absolutely true what he’s saying, and Sinatra was still always okay with that? Rickles never went too far?

JK: I don’t think he ever did, unlike Jackie Mason, who got the crap beaten out of him, and Shecky Greene, who got the crap beaten out of him. I think in each case their sin was doing the material when Sinatra was not present; not doing it to his face. Sinatra just heard about it. Although, Shecky Greene had no fear of Sinatra, and he may have made some of the comments in Frank’s hearing. Shecky, who’s still with us, is a madman. He’s a total madman. He was a great comedian: a great, uncategorizeable comedian. Sinatra loved him, and he hated him when he made those remarks, and there is the famous joke that Shecky Greene made and keeps making: “Frank Sinatra saved my life one night. Three guys were beating me up in the lobby of the Fontainebleau hotel and Frank said, ‘That’s enough.’”

RA: That’s still a good one. Let me switch gears a little and go back in time to your earlier book. I think it’s fair to say, that before Frank Sinatra there was crooning, and after Frank Sinatra there was singing. How did this young man change popular song and how it was interpreted and performed? Why him?

JK: I think that that’s not entirely true. I think that before Bing Crosby there was crooning, and then there was Bing Crosby, and then there was Frank. Sinatra heard Crosby, who was not a crooner. A crooner is a high-voiced, artificial-sounding singer like Rudy Valley or Russ Colombo. The crooners were the singers who first came along before the electric microphone, and so they had to croon in order to be heard at the back of the house in theaters; high voices were heard better.

Crosby came along and utilized the microphone to its fullest advantage. Crosby sounded like a guy who was just singing in the shower: like an ordinary guy, except that the voice happened to be amazing, and the timing and the expression were amazing. Sinatra idolized Crosby, but in this completely Oedipal way: determined to knock him over to become the best singer around. From the start, Sinatra’s was a very beautiful voice, but it lacked the stilted quality of the crooners. The crooners had these high, androgynous-sounding voices, and there was sometimes an artificial English accent to make everything sound distinguished.

Crosby was talking to you, and Sinatra was talking to you. They were very different voices: Crosby was cooler, Sinatra was much warmer. There was an intimacy in Sinatra’s voice that nobody had ever heard before. It was not only a beautiful voice, but it carried this x-factor, even as the voice changed dramatically from decade to decade — this sense that he was feeling the feelings, thinking the thoughts that he was singing about in the instant that he was singing about them.

Crosby conveyed intimacy, but Sinatra brought vulnerability to American popular song. He had heard this in Billie Holiday, and he brought his own brand of it. It was enormously seductive and appealing to young women. They didn’t even know what was getting to them. There was something unconscious about it. It got to women and young women on an unconscious level. This expression of vulnerability, together with this magnificent, beautiful, young voice, just made him absolutely addictive and indispensable.

RA: You don’t feel like the young Sinatra was really just trying to sing like Crosby?

JK: Nope.

RA: And then later he lowers —

JK: Nope.

RA: — his voice —

JK: Nope. Nope.

RA: — and accepts his baritone?

JK: Nope. Nope. Nope. It is apples and oranges. Let’s not forget that from when Crosby started out until Jack Kapp got ahold of him and forced him to change it up, Crosby was an amazing jazz singer. Then Kapp forced him to concentrate on ballads. There is great beauty, and it’s impossible to say it any other way, but there is a kind of cool intimacy in Crosby’s singing. Sinatra was never cool. He was warm. He was hot.

It was Jo Stafford whom I had the privilege of interviewing, before she left us. She sang with Sinatra in Tommy Dorsey’s band, and she called him a warm Italian boy. You could see that as a flip characterization, but it wasn’t: she meant exactly what she said. She was talking about that voice. It conveyed a warmth and an intimacy that had really never been heard before. There are a lot of terrific voices out there: there was Bing Crosby, and there was Jack Leonard, who had sung for Dorsey before Sinatra came on the band. There were all kinds of very, very good voices, but they were just voices. They didn’t convey that immediacy of emotion, they didn’t convey the warmth and the heat that Sinatra conveyed. It’s a totally different thing from Crosby.

RA: This seems demonstrated a lot by the album you talk about they recorded of patriotic tunes, and how they each approached it and how it came off.

JK: Yeah. Bing said his famous quote about Sinatra: “Sinatra is the kind of singer that comes along once in a lifetime. Too bad it had to be my lifetime.”

RA: That’s very generous, considering.

JK: Very, very generous. And Bing Crosby was and remains a toweringly great artist. Unfortunately, his reputation, his legacy, doesn’t hold up with nearly the strength of Sinatra’s.

RA: One of the things that stunned me in your book is that the Playboy interview is a fraud.

JK: Yes.

RA: How did you stumble into that? Was that widely known before?

JK: No, it was not widely known before.

RA: This is a famous interview of Sinatra. These quotes are well known by Sinatra fans.

JK: Yes, of course, and they’re all attributed to Sinatra: “18-karat manic depressive,” “I’m for whatever gets you through the night, be it prayer, tranquilizers, or a bottle of Jack Daniels.” Yeah, there are at least three or four of these very, very famous quotes. Mike Shore was a genius, and I found him. I had heard the rumor that he was responsible for the interview. I interviewed the now late Stan Cornyn, who had written liner notes for Sinatra and was a strange and wonderful man, and when I asked him if Mike Shore was around anywhere, Stan Cornyn said, “No, I think he died a few years ago.” Well, I did some more hunting and Mike Shore was very much alive. He was 90. I talked with him a lot, and I met with him in L.A. Fascinating, fascinating guy. I wish he were still with us because there are a lot of questions I would still like to ask him.

RA: I have a couple. Did Sinatra see the answers before they were submitted?

JK: Yes, yes, yes. He rubber-stamped it. He loved Mike Shore. Again, Sinatra was an amazing talent scout when it came to hiring anybody, when it came to appreciating brilliance. So he knew that Mike Shore was brilliant. Mike Shore wrote advertising copy for Reprise Records and came up with all kinds of ideas. He knew Mike Shore was a brilliant guy. They had suggested this guy, Joe Hyams, Playboy had, to interview Sinatra, and he was on Sinatra’s shit list by that point. He did not want to sit down with Joe Hyams or any interviewer; he’s too impatient for it. So he just had Mike Shore write it up and he looked at it, and he thought “Oh, well that sort of sounds like me, and it sounds great. Great, terrific. Print it.”

RA: How close was it to Sinatra? I mean, was he somebody who didn’t particularly believe in God?

JK: Yes. I think it was close to Sinatra. I think that you can read that interview as a strange kind of parallel-universe autobiography. Mike Shore was an enormously intuitive man and verbally brilliant, and Sinatra again recognized this, and, as Mike explained to me, he understood Sinatra very well. He felt he understood Sinatra intimately, and I think that Sinatra understood that Mike Shore understood him, and Sinatra enjoyed being understood. And enjoyed being made to sound so incredibly articulate. The guy is holding forth on the world’s religions and Bertrand Russell and Mahatma Gandhi and he’s got opinions at his fingertips on everything. Mike Shore not only knew how to channel Sinatra: he knew how to flatter the hell out of him. It was a perfect combination.

RA: Some of the talented people in Sinatra’s life, particularly at the end, he had terrible endings with. I’m thinking of Nelson Riddle. Sinatra blew off an important award that he was supposed the present to Riddle. It torched the relationship.

JK: It’s unclear how that happened. It might have been a misunderstanding, but it wound up being a terrible insult to Riddle. Riddle was a guy who was a gloomy man and he was always inclined to think less of himself than he should have. He’s a gloomy and self-deprecating man who’s huge flaw it was that he was a historically brilliant arranger, of course, but he wasn’t a great composer. Unlike Henry Mancini, Neal Hefti, André Previn, he couldn’t churn out commercial tunes that could bring in big revenue. So he was always scrounging, he was always over-extending himself. He probably worked himself to death, and, much like Sinatra, he was very, very oversensitive to slights. When Sinatra first went to Gordon Jenkins in 1957 to arrange an album, Riddle was mortally offended. He was mortally offended each time Sinatra picked another arranger, and this was the final insult, Sinatra’s not showing up at the testimonial.

RA: And yet, Riddle is, I think it’s fair to say, the greatest arranger Sinatra ever had, and the partnership they had is what resulted in Sinatra’s best pieces.

JK: I think that he’s the greatest arranger of popular music there ever has been.

RA: Did Sinatra appreciate Riddle that way?

JK: Yes, he did. And his going to other arrangers does not reflect any disrespect for Riddle. It only reflects Sinatra’s brilliant idea of keeping it fresh, of looking for new sounds. Riddle could write in any style, but Sinatra knew that by going to Gordon Jenkins he was going to get something that Riddle couldn’t quite do. Billy May was Billy May, and the albums were bright and brassy and bouncy. I think it was partly a desire of Sinatra’s just to hang out with somebody else for a little while. It was much like what drove him to constantly find new lovers. He was restless, impatient, always wanted the best new thing, and Riddle couldn’t see it. I guess maybe he did see it, but it hurt him badly because he knew that Sinatra was the greatest artist he had ever worked with and would ever work with.

RA: I think that’s probably true for most of those. I mean, maybe Axel Stordahl didn’t know, but that was early.

JK: Stordahl knew. They knew. They knew.

RA: Let’s focus on Riddle for just one more question. Gordon Jenkins could do beautiful ballads, Billie May could do great bouncy songs, but somehow with Riddle it had a certain sound that wasn’t there any other way. I can’t put my finger on it. I was wondering if you thought that way as well.

JK: Yeah, absolutely. The finger to put on it is that Riddle was just far more deeply schooled in the classics and loved the French impressionists, loved Ravel, Debussy, Jacque Ibert, and had this unique ability to take these strains, these strands, these threads from classical music and weave them together with great jazz. He loved Sy Oliver; he loved the great black bands of the swing era. Jimmie Lunceford was a huge favorite of his, and of course he played, Riddle did, with Dorsey. And he was able to weave together these two strands in a way that nobody else really could. None of these other arrangers could. When it came to hearing impressionist tonalities, he just saw musical color combinations that nobody else could.

RA: Another aspect that you cover in The Chairman: one of the great Sinatra mysteries is his swing from a very active Democrat to a Republican in the ’80s. What happened?

JK: Well, a lot of it had to do with vendetta. His mother was from Genoa in the North and his father was from Sicily. Sinatra had a lot of the Sicilian in him, and vendetta is a centuries-old Sicilian tradition. Sinatra could be very vengeful when crossed or when he felt he was crossed. And so it was a combination of a couple of factors, almost like different weather fronts moving in. One had to do simply with his getting older and more conservative. Another had to do with the political turbulence in the world in the late ‘60s, but a great deal of it did have to do with vendetta.

It had to do with this incident in March of 1962, when President Kennedy had been going to spend a few days at Sinatra’s Palm Springs place for some R&R. And what R&R meant to President Kennedy was that his wife, Jackie, was traveling in India. The cat was away, and Kennedy was eagerly anticipating having some naughty fun at Sinatra’s place. However, J. Edgar Hoover, the head of the FBI, had recently informed the Attorney General of the United States, Bobby Kennedy, that the President was sleeping with a young woman named Judy Campbell, and that Judy Campbell was also sleeping with Sam Giancana, the head of the Chicago mafia, and furthermore, that Sinatra had made the introduction in each case, specifically with the intention of ingratiating himself to both these men.

Hoover was very aware of this; Bobby Kennedy was very aware of it. Bobby Kennedy told his brother, “you may not stay at Frank Sinatra’s place, ever,” so Jack Kennedy on his westward swing stayed at Bing Crosby’s place in Palm Springs. And Sinatra, who had completely remodeled his Palm Springs Place in anticipation of the President’s arrival and had built a concrete helipad and installed a hotline red telephone — he went ballistic. The legend is he went out to that helipad with a sledgehammer and started chopping away at it: hacking and pounding away at that helipad. He was so furious he ripped the red hotline out and smashed it against the wall. It was a huge public humiliation. He blamed it on the bearer of bad news, Peter Lawford, the President’s brother-in-law, but he also blamed Bobby Kennedy. And that began his disaffection. He never blamed it on the President, oddly enough.

Fast forward six years: JFK’s dead and then Bobby Kennedy gets assassinated. Sinatra campaigned for Hubert Humphrey in the 1968 presidential campaign. Humphrey’s advisors quickly whispered in his ear that Sinatra had some not-so-great friends and maybe he should stay away from Sinatra. So Humphrey dropped Sinatra. It’s 1968 and the world is on fire and the counterculture is rearing its head, rock ’n’ roll has completely destroyed the popular music business as Sinatra knew it, and the SDS [Students for a Democratic Society] is running across college campuses, everything’s burning, the assassinations, the Democratic National Convention in Chicago was chaos, and Sinatra has turned 50, and he’s getting on, and he’s scared. He hates all this disorder.

RA: He previously hated Nixon, right?

JK: He had hated Nixon. He had hated Ronald Regan, but suddenly here he is. He’s not campaigning for Nixon yet. That happens in 1972. The first step in Sinatra’s turn to the right is his campaigning for Ronald Regan, who was running for governor of California in 1970. Sinatra’s Democratic friends are utterly aghast that this guy who has been an FDR liberal since the early 1930s is suddenly campaigning for this guy whom he had derided very publicly as a total bozo. Sinatra is suddenly saying, “I can still be a Democrat, but I can support whoever I want.” That was the end of Sinatra and the Democrats, and in a couple of years, he’d be playing golf with Spiro Agnew and cozying up to Richard Nixon — a decision that he would very quickly come to regret.

Sinatra receiving the Presidential Medal of Freedom from Ronald Reagan in 1985
Sinatra receiving the Presidential Medal of Freedom from Ronald Reagan in 1985

RA: Let’s move to the sad end. Your book doesn’t end with Frank Sinatra’s 1972 retirement: you have a coda, but that coda covers the last, what, 20-25 years of his life?

JK: It does. It is a very different part of his life, and to my mind it is a less complex part of his life. It is more monochromatic. Sinatra comes back from the ’71 retirement as a totally different artist. He is not really making movies anymore — just one or two, here and there — he has changed physically: he’s thicker, his head is rounder, there’s a lot less hair. He doesn’t want to be on camera that much anymore. He’s not making record albums so much anymore, and in a certain way he is prescient in this.

You talk to young musicians today and they’ll tell you: they don’t make any money selling records, they make money touring. Sinatra recognized this in 1974. So he recast himself as a purely concert artist. The story of the last 20 years of his career, 1974 to 1995 (February of ’95 was his last concert), is a story of relentlessly being on the road. By the testimony of Tina Sinatra, she says that Barbara Sinatra, Frank’s fourth wife, kind of kept Frank on the road even though Frank was beginning to lose it. His mental powers were fading, and there were bad moments. None of us end well, but Sinatra had to end in public. His decline was very, very public.

There were some excellent concerts along the way. I saw him at Carnegie Hall in 1981 — he was staggeringly great — and a lot of people have told me they saw him in the mid-80s and even in the 90s and he could still be great, but less and less so. More and more often, people were just coming out to see Sinatra. The voice wasn’t there, the memory for lyrics wasn’t there, but it was still Sinatra.

RA: The period that he retired was just a couple years. Why was the change so dramatic? On The Main Event, you can tell it’s a different man singing on that album.

JK: Yeah. A lot had changed. All the changes that I noted — the changes in the popular music business, the physical and mental changes in Sinatra, the change in the culture at large — he had to work harder to capture the effects he wanted to capture. He had always respected his singing to a huge degree: he even went into training before he made record albums, cut down a little bit on the three packs of unfiltered Camels he smoked a day and the fifth of Jack Daniels he drank a day. For The Main Event, he was about to turn 59. Even though he made it to 82, astonishingly, Frank Sinatra was an old 60 years old. He had not taken good care of his body, and he continued not to.

Two things about the time off: one, he was wise to take it, but when he realized that the world needed Sinatra and he needed the adulation, he came back. I think the time off was also hard on him. I think it showed him an impossible fact about his life: that he needed to retire and he needed to work. He needed those things simultaneously; he needed them badly.

At that point in 1974, he had been performing steadily and at a pace none of us could really imagine for 35 years. And you look at the length of that career and try to compare it to any other artist — you can sort of understand it on paper, but it’s kind of inconceivable. I think all these factors converged in 1974 when he came back to make him a very different guy on stage than he had been before. He was also richer, he was more politically conservative, he was more entitled than ever. There was some sad, bad truth to some of the caricatures that began to be put forth by Joe Piscopo and Phil Hartman on SNL. There was a certain brutality to his public persona when he came back, but again, when I saw him at Carnegie Hall in ’81, it was a glorious concert. He was charismatic and the singing was amazing.

RA: Let me ask you, talking about this great, late concert: How much Sinatra is there unreleased? Are there studio recordings that he never put out? Are there lots of concerts on tape? Is there an archive we don’t know about?

JK: Yes, there’s a mountain of material. I just happen to have everything because my good and extremely generous friend, the world expert on Sinatra music Will Friedwald, gave me a hard drive full of everything when I began my research ten years ago — all the outtakes, all the studio sessions, all the rehearsals, everything, everything, everything. Not all of it keeping strictly in line with the Sinatra family’s wishes or legal restrictions. It’s a 60-year career, from 1935 to 1995, and a great deal of it was recorded. So, I can easily imagine over the next decades more and more previously undiscovered, unreleased Sinatra material coming to light. This new four-CD set, Sinatra: A Voice On Air, just came out. That’s Sinatra radio recordings, and this is all new material, previously unheard and beautifully mastered. At this point in my career, I am not restlessly seeking out new Sinatra material. I will say that, over ten years of working on these two books, I never got bored with him, and that I still get goosebumps when I hear him sing. •