Few musicians were ever as popular, influential, complicated, or dangerous as Frank Sinatra. Between landmark albums like “Songs for Young Lovers” and “In the Wee Small Hours,” his movie acting (“From Here to Eternity,” “The Man with the Golden Arm,” “The Manchurian Candidate”), his marriages to Ava Gardner and Mia Farrow, his running with the Rat Pack and brushes with the mob, he led a full, at times overstuffed life.
Biographer James Kaplan now follows his acclaimed “Frank: The Voice” with “Sinatra: The Chairman,” a thick, almost 1,000-page volume that aims for the level of depth and context Peter Guralnick achieved with his Elvis Presley biographies. Kaplan’s book both gets up close -- using detail the way a novelist does -- and weaves Sinatra in with the era he lived through. “The Chairman” emphasizes the period from 1954 to his 1971 retirement; it closes by moving quickly through Sinatra's return to performing.
We spoke to Kaplan about Sinatra’s temperament, his acting, and the influence of jazz on his singing. The interview has been lightly edited for clarity.
Can you characterize the period of Sinatra’s career and life? It’s really the mature and great and established Sinatra, isn’t that fair to say?
Yes, it is. My first volume covers Sinatra from birth until the night he wins the Oscar for "From Here to Eternity" in ’54. And so, it includes his rise as a romantic young singer, his explosion as a superstar in World War II, and then his collapse, in career and personal collapse post-World War II. The end of that book is the beginning of a comeback, and Volume II picks up that story 11 days after the Oscar, where Sinatra was writing a thank-you note to a friend for congratulating him on the Oscar.
And, the first book is the story of the rise of a young, romantic troubadour and the second book is really a book about power. It’s a darker, tougher book. And it’s a book that even with World War II and the big band era fitting into Volume I, Volume II covers a lot more of American history and a lot more of popular culture than Volume I does. There’s more to put in it. But yes, your assessment is exactly right. Even as Sinatra acquires enormous temporal power in the mid ’50s and on into the ’60s, he’s also putting together a string of the most astonishing albums of popular music—creative to date, and in many ways, still to this day.
How many years did you spend on this one? I’m wondering if the huge amount of research and interviewing change your view of him, either as a man or a musician?
Each of the books took me five years. Roughly speaking, with each of them, about three years of research and two years of writing. Research, including reading everything — books, newspaper articles, gossip columns, everything, and then, hundreds of interviews. It’s an enormous undertaking and of course, my feelings about Sinatra evolved as the project went on. When I began it, I was kind of, looking back, miserably ignorant of Sinatra. That is to say, I knew who he was, I knew how great he was, I knew he had created this music. But as to the specifics of this career and the complexities and subtleties of his life, I knew little if not nothing. I knew a lot of the clichés that had become widespread about Sinatra.
But it was my job to get behind those clichés, and to give the reality dimension and to shoot down any falsehoods that had been spread. One thing I’ll say is, the cliché about biographers is -- it’s an unfortunate one -- after a long time of working on the book they’re working from a contempt for their subject.
And it never happened to me. He was a genius and he was a genius in several ways, and one genius that he possessed besides his musical genius was a genius for making himself dislikable. So there were many times when I disliked him. He could be awful, he could be quite awful; as Pete Hamill said, “His shortcoming were regrettable.” He’s putting it very kindly.
His shortcomings were large on the world. But I never felt contempt for him; contempt is one thing but dislike is another. I never -- and this is more important still -- never got bored with him. And I’m still not. And what’s more is I get goose bumps when I hear the guy sing. It’s an astonishing voice, and it’s beyond astonishment really, it’s inexplicable. There’s all kinds of things that I can say what it is, and there’s all kinds of things that I can’t say.
The explosive moment of my pre-adolescence was seeing the Beatles on February 9 on the Ed Sullivan show. And I loved rock ‘n’ roll, I continue to love rock ‘n’ roll, I listen to all kinds of music. I love classical, I love jazz and another evolution for me, studying Sinatra, was realizing that studying Sinatra and his music was not looking at a nostalgia act. It was not looking at something old-fashioned, or big band-er or your father’s cardigan sweater. It was looking at the greatest, arguably the greatest, interpretive musician of all time. And that includes everybody.
Let’s talk about Sinatra’s temperament for a minute. During that period, he was enormously popular, enormously powerful, feared in some cases. He was also despairing some of the time too. He tried to kill himself in the early ’50s over Ava Gardner; he could’ve died. Did he remain haunted, frustrated and insecure, even through his most successful period?
Yes. I think he was a tormented man. Listen, this was a guy who said that when he was a kid he heard the music of the spheres. This is a little Italian kid walking around Hoboken, New Jersey, in danger of getting beaten if he walked into the wrong Irish-American neighborhood or African-American neighborhood. It was important, when he was growing up, to be tough. It was important for him during his whole life to be tough, but this was a guy who was an out-and-out a musical genius, who heard too much, who felt too much. He was beyond high-strung. He was exorbitantly oversensitive, and that was a quality he felt he had to shield from the outside world.
He had to put on this shield of swagger, bluster and masculinity. He was a little man. He was an Italian-American who grew up at a time when Italian-Americans were just a half step above African-Americans. Italian-Americans were not legally considered white until sometime in the 1940s. It was crazy.
That explains a lot about his attraction to the mafia. These were guys who seemed powerful to him, strong, and honorable, and unfortunately he had a crush on them. He idolized them like a small boy idolized cowboys or soldiers. But, he was a little guy. He was 5' 7". Until the mid-’60s, he was very skinny, had slight delicate wrists, artistic hands and small feet. He was over-sensitive, strung way high and a genius to boot.
He was really a tormented guy in lots of ways. He had horrible parenting. He had a father who was distant and a mother who he never knew whether she was going to hug him or hit him. And she did hit him. His mother and father ran a bar in Hoboken. They had a billy club behind the bar, and she slung him with it when he got out of line. And one time on the Jersey shore, she pushed his head underwater, under the surf, apparently just for the hell of it. She was extremely unpredictable. His parents were frequently absent.
He was very similar to his mother. She was pathologically impatient, had a volcanic temper, just like him. And so the whole combination made him a bundle of woe in many ways. He hated the night. He was scared of the dark. He was afraid to go to sleep. He needed company at all times until he finally turned in at about 7 or 8 a.m. He had many demons. I am not excusing his bad behavior, which he stoked with alcohol, and which grew worse with power and entitlement.
But he was guy who was never really happy, except for the times when he was singing well. And his standards were so superlative that he knew when he was singing well, and when he was singing poorly. And most of the rest of the time, seven-eighths or nine-tenths of his life, he was just from one thing onto the other. He was terminally impatient, and deeply dissatisfied always.
The ’50s was a great period for him. How did the change the ’60s brought, musically and otherwise, hit Sinatra?
It hit him hard. It destroyed the music business as he knew it. He hated rock 'n’ roll. He hated Elvis, when he came in in the mid-’50s. He detested rock 'n’ roll, and suddenly, here’s the apotheosis of rock 'n’ roll, and the music business is completely turned on its head. Everything, the American songbook, was not fallen by the wayside, but was becoming old hat in the blink of an eye. He had started this new record company, Reprise, in the 1960s, and it was a flop right out of the gate. He couldn’t sell records.
He signed up all his old pals, Dean Martin and Pearl Bailey, and people like that, for his new record label, but he couldn’t sell records until the guy he had hired to be in charge of his record company, a guy named Mo Ostin, started signing rock 'n’ roll acts. Reprise was about to go down the tubes, until 1963, when Jack Warner, head of Warner brothers, decided he had to have Sinatra as a movie star.
Well, Sinatra had a brilliant lawyer named Mickey Rudin, who met with Jack Warner, and said, “You could have Sinatra as a movie star, but you got to take the record label too.” And Jack Warner said, “Anything. Anything!” And he put several million dollars in Frank’s pocket. The labels merged: Warner and Reprise. Mo Ostin, as head of Reprise, began signing rock n’ roll. He signed The Kinks. Suddenly, they were making money, hand over fist, but only because he was signing rock acts. Frank loved to make money, but he hated rock 'n’ roll. So yes, he was somewhat conflicted.
How important was Sinatra’s acting to him, and how substantial does it seem? It wasn’t just a side project to his music career, was it?
Yes, it was more than that. First thing to understand was that when Sinatra was performing in a club, or in a recording studio – those recording sessions were performances, there was always an audience. He always brought in a gallery full of friends, acquaintances, hangers-on to every recording session. Every Sinatra performance was acting. His greatest performance was as himself.
The one time I saw him was in 1981 in Carnegie Hall, and I went with my tongue in my cheek. Growing up and seeing Phil Hartman and Joe Piscopo make fun of Sinatra, I was expecting something clownish, and I went and this guy was the greatest performer I had ever seen.
I had seen a lot of rock 'n’ roll in my time. I saw The Stones. And he was just incredible. He was an actor. The first person he ever idolized was Bing Crosby, and Bing Crosby became a superstar in the 1930s not only by selling records, but also by acting in movies.
He knew that his best take was his first one. He was a very untrained and instinctive actor. He was almost always, on a movie set, a total pain in the ass, and it all depended on his relationship with the director and his feeling about the property that he was acting in. Almost always, after MGM canned him in the early ’50s and he went out on his own, he was Frank Sinatra the superstar who was basically in charge of the production. And once he took over, once he was bossing the director around, all bets were off. And so he made a lot of crappy movies. But there were exceptions. There were people he couldn’t boss around, he didn’t want to boss around. The first big exception after MGM was Fred Zinnemann making from “From Here to Eternity.”
Sinatra was on his uppers, his career had gone down the tubes. He was desperate to come back, and not only that, but Fred Zinnemann was a brilliant director, a courtly and gentle and intelligent European whom Sinatra had great respect for. And Sinatra busted his ass to do that job in “From Here to Eternity” and deserved every bit of the Oscar he won. He did a wonderful job.
The other two exceptions I would say -- with an asterisk for Vincente Minnelli in “Some Came Running” in 1958 -- would be Otto Preminger’s “The Man with the Golden Arm” in 1955, where Sinatra played a heroin addict, and always felt that he deserved another Oscar for that. I differ — I tend to think that that movie is stagey and dated and that Sinatra was chewing the scenery, but he did do a good job in that movie and he respected Preminger and worked hard. And I feel Sinatra’s greatest movie of all was “The Manchurian Candidate” in 1962.
It’s a great movie, and John Frankenheimer was a brilliant director, brilliant young guy, much younger than Sinatra. And Sinatra didn’t have to behave for John Frankenheimer, John Frankenheimer was not only brilliant -- he was as tough guy. He was a jock from Queens, and he was not going to take any shit from this little Sinatra.
But not only that, he wasn’t just a tough guy, he was a great director, brilliant guy, and it was just a brilliant project from the get-go between Frankenheimer and his writer George Axelrod. It’s a staggeringly great movie. Other than that, the movies he made tend to be either regrettable or entertainments. You can watch “Pal Joey,” and “Pal Joey” is a fun musical. You can watch “Guys and Dolls” and for all the negative people said about it, and how Sinatra and Brando should have reversed roles -- I like the movie. It’s fun to watch.
“Ocean’s 11” is a terrible movie but it’s fun to watch. It’s seminal and it is definitively politically incorrect, and it’s the Rat Pack and it’s naughty fun, and Sinatra was bossing the hell out of that poor director Lewis Milestone. It’s a bad movie but it’s a fun movie.
And the Tony Rome movies – [like] “Lady in Cement” where he’s playing a private detective. Those two were really the roles that were closest to Sinatra as Sinatra. Those were fun movies to watch. Not great movies by any means, but fun.
Right, right. Well, the real genius of Sinatra I think is in the phrasing. I wonder how much of that came from his love of jazz musicians… Billie Holiday, Lester Young, and Ella Fitzgerald -- how much of phrasing is indebted jazz singers and horn players?
All of it. All of it! Billie Holliday was almost the same age as Sinatra. She was born, I think, eight months before Sinatra in 1915, and yet she became a success very, very young with Teddy Wilson, with Count Basie, and with Benny Goodman.
So when Sinatra was a punk kid, a teenager, he used to go to 52nd Street in New York between Fifth and Sixth. Now it’s just office buildings. But back then it was this long row of brownstones, both sides of the street, and it was full of jazz clubs. You could walk from door to door and hear these geniuses. You could hear Lester Young. You could hear Teddy Wilson. You could hear Billie Holiday -- and he did. And this was not only the basis for his phrasing and for his love of jazz, it was also the basis for his admittedly flawed, conflicted sense of tolerance his entire life.
He was a guy who thought it was obscene and absurd that black people were discriminated against, and yet this was also a guy who could make horrible “Amos and Andy” jokes on-stage at the Sands, who could say things about eating watermelon. He thought he was entitled to.
But when you watch “A Man and His Music, Part III,” the great TV special he made in 1967 with Ella Fitzgerald and Antonio Carlos Jobim, you watch Sinatra with Ella and he was not only vastly respectful of her and not only learned a ton from her, he was in awe of her. He was even kind of intimidated by her.
So the answer to your question is, All of it. He loved jazz. He loved jazz musicians. He loved listening to them and he learned that great secret of just staying a little bit behind the beat, keeping the listener hanging and wanting a little bit. It was a great secret, and he learned it from the great horn players. But first from Billie.