Capturing the Genius of an American Icon

Capturing the Genius of an American Icon  James Kaplan ’73 is the author of the acclaimed new biography, Frank: The Voice (Doubleday, hardcover; Anchor, paperback), about the early life of one of America’s best known American singers and entertainers of the 20th century, Frank Sinatra, from the years 1915 through 1954. Kaplan reveals how Sinatra helped to make the act of listening to pop music a more personal experience to his fans than it had ever been before. Book critic Michiko Kakutani of The New York Times chose Kaplan’s book as one of the top 10 books of the year, and it quickly became a Times best seller.

Last spring, Kaplan was the Wesleyan Writing Programs’ 2011 Joan Jakobson Visiting Writer and he spoke toWesleyan magazine about his new book.

DAVID LOW: Sinatra has been the subject of numerous books. What made you decide to choose him for the subject of your first biography?

JAMES KAPLAN: I was fascinated by Sinatra. I’m from New Jersey so there’s some geographical connection, and I loved his music. When I started reading Sinatra biographies, what I discovered was that there was a lot about the fistfights and the mob and the women, but somehow, the writers hadn’t put the genius on the page. What I wanted to try to do, despite the fact that Sinatra has been more written about than any other human being in modern history, was to write a biography of empathy, and to try to get the genius onto the page.

DL: Would you talk about Sinatra’s growing up in Hoboken, New Jersey?

JK: Sinatra hated Hoboken. When he was growing up in the 1920s and 1930s it was a tough, blue-collar port city. He grew up at first in a part of town that was called, and I’m just quoting, “guinea town.” That was the Italian section of Hoboken. It was very poor, with row houses.

His father, Marty, was illiterate and didn’t say much. He had been a prizefighter, not a very successful one. He had tattoos all over his arms. Through his wife’s political pull, he got a job as a fireman and eventually as a fire captain in Hoboken. Dolly, Frank’s mother, was a dynamo: under five feet tall, fiery and brilliant. She spoke every dialect of Italian, which was very useful where they lived. Dolly quickly became a kind of political force in Hoboken, and eventually became a Democratic ward boss. She was a suffragist—in 1919, she chained herself to a fence to protest women’s inability to vote. She had a volcanic temperament and was deeply impatient, characteristics she shared with her son.

Sinatra was a forceps baby, born in 1915. Hoboken then was still a town of horse-drawn carriages with few automobiles. It was like the 19th century—many children died at birth and many mothers died giving birth. Dolly just survived the ordeal. Frank was yanked out with forceps, which badly damaged the left side of his face, leaving bad scarring. His left ear was mangled. And then when he was a child he had a mastoid operation which led to further scarring of his ear and his neck, just at the back of his ear. As an adolescent he had severe cystic acne, which deeply pitted his cheeks. He thought of himself as kind of deformed physically, and his birth had a lot to do with that.

Sinatra was also an only child, an extreme rarity in those days, especially among immigrants. As an ethnic group Italian Americans were extremely low in the social order in those days. In the sort of perverse social hierarchy of America in the 1920s and 1930s, Italian Americans were just a step above African Americans. In fact they weren’t legally considered white. There were a lot of chips on a lot of shoulders in Italian American sections of cities around America and Hoboken was no exception. Throughout his life, even as Sinatra acquired huge amounts of wealth and status and fame, he kept that chip on his shoulder. I think this feeling of being one down drew him to the mob, many of whose members were Italian Americans. He saw them as men of power and honor and he idolized them.

DL: Would you comment on his early rise to fame, and his years singing with band-leaders Harry James and Tommy Dorsey?

JK: In the start of his career in the early and mid-1930s, Sinatra was always trying to convince people that he really could sing. His voice was not the great Sinatra voice at the start. He was, however, born with a genius ear for music—he said in later life that at 9 years old he heard the music of the spheres, and I believe something like that was true. Largely through his mother’s help, he got a job as a singing waiter at the Rustic Cabin nightclub on the Palisades of New Jersey, near what is now the George Washington Bridge. The place had a radio hookup and the music there could be broadcast to WMCA in New York City.

Harry James, a great swing-era trumpeter and bandleader, was married to a beautiful singer named Louise Tobin. One night Tobin heard Sinatra on the radio and said to James, “I think you ought to hear this kid.” So James made it his business to go to the Rustic Cabin. Many years later he said when he first heard Sinatra sing the hairs went up on the back of his neck. He hired Sinatra in the spring of 1939. But as brilliant a musician as James was, he was a terrible businessman, and as he and his musicians toured the country, the band was falling apart because he didn’t have the money to pay them.

When they got to Chicago after a very unsuccessful westward swing, Sinatra auditioned for Tommy Dorsey, who was a great trombonist, bandleader, and businessman. He ran the Rolls-Royce of big bands and made big money. His musicians all wore exactly the same thing, and if a lapel or a necktie or a lock of hair was out of place, the offender would get fined. But Sinatra was thrilled to be signed by Dorsey, who also knew how to feature singers. Singers in the era of big bands were secondary; they were the voice that came in after the long, lyrical, instrumental intro by the bandleader. The singer would then vocalize for a minute or so, then the bandleader would play a long, lyrical outro and the song would be over. The spotlight was strictly on the bandleader.

This quickly changed when Sinatra joined Dorsey’s band. Sinatra had something special in his voice that caught the ear of every adolescent and post-adolescent female on the road. Hearing the Tommy Dorsey Band, they all went nuts for him. He was very skinny in those days, he had those electric blue eyes, he looked like he could use a good meal, and he had learned very early to project the appealing vulnerability that he really possessed. He was unsure of himself in a lot of ways but masked it with bravado. His vulnerability was extremely sexy to women. He would put a little catch in his voice when he was singing, and the women began to scream.

DL: This was a long time before Beatles mania, wasn’t it?

JK: This was 15 years before Elvis, 25 years before the Beatles. Nothing like this had happened in America before. Bing Crosby had been a huge idol, yet his fans had cut across all age groups. But with World War II, a social group arose that had never existed before. Suddenly adolescents had disposable income: they could buy records. Frank Sinatra’s fans were mostly adolescent girls, and they bought his records like crazy. Little by little, Sinatra became the star of the band instead of Dorsey.

DL: What was Sinatra’s approach to singing a song?

JK: The big surprise for me in doing this book was how incredibly hard Sinatra worked on his singing. He studied voice. In later years, there were a lot of myths about Sinatra, and he spread a lot of them himself. One of them was that he never had a voice teacher. That’s not true. An ex-Metropolitan Opera singer named John Quinlan worked very closely with Sinatra in his early career. Quinlan stressed superb diction, which was extremely difficult for Sinatra at first, given his strong New Jersey accent. There are recordings of early radio broadcasts that are unintentionally hilarious—Sinatra will be speaking to an announcer or bandleader and he sounds like pure Hoboken, as if he’d just gotten off work at the docks. Then suddenly he goes into this song, and his diction is perfect. When there is a “wh” as in “who” or “where,” it’s always aspirated. Every syllable is crisp yet flowing.

Dorsey taught Sinatra a great deal about breath control. But another important lesson Frank learned from Tommy, whom he idolized, was that the words to the song were all-important. Sinatra understood from the beginning—I think this is part of his genius—that the way to really rise above other singers was to communicate a song, not just to sing it, not just to be a pretty voice that was the bearer of the song, but to really tell a story. So he would read the lyric of the song, and he was learning it before he ever sang a note. He would read the lyric as if it were a poem.

DL: Would you talk about Sinatra’s relationships with women, particularly with his first wife Nancy and then later with Ava Gardner?

JK: It’s a cliché that bears deep truth that a man’s relationship to women has a lot to do with his relationship with his mother. Sinatra said he was very uncertain about his relationship with his own mother. She could be brutal to him. Dolly Sinatra used to whack her son with a billy club when he got out of line. It didn’t do much for his relationships with women. He was often very tough on them. Nancy Sinatra, his first wife, was beautiful in a very ethnic way. She had a sort of street quality. She was from Jersey City, the town next to Hoboken. I think that she and Frank really did love each other but the classic whore/Madonna thing was a very strong part of Sinatra’s consciousness and Nancy Sinatra was a Madonna as far as he was concerned.

Early in Sinatra’s singing career, in the mid-1930s, women began to be drawn to him like moths to the flame, and he gladly accepted all comers. He loved women, but I also think that perhaps his insecurity about his looks made him a little more likely to be promiscuous from the beginning of his career. Nancy decided to look the other way as long as he came home to her.

When he went to Hollywood in 1943, though, he became more famous and more photographed and his adulteries were written about in gossip columns. His affairs were with progressively more beautiful and famous women, eventually culminating with Lana Turner, who was the great movie-star beauty of her day. The two of them were photographed dancing together; Sinatra looked as giddy as a schoolboy, and his wedding ring was clearly visible in the picture. He looked like a newlywed, but it wasn’t his wife he was dancing with, it was Lana Turner. After a while Nancy had just had enough, but she didn’t finally boot him out until he took up with Ava Gardner.

DL: What was different about Gardner?

JK: Gardner really was a force of nature—the kind of beauty that comes along once in a hundred years. A number of people I’ve talked to for the book said that just watching her walk across a room was amazing. She was kind of the female version of Sinatra—very similar to him in a lot of ways, except for the fact that she was incredibly gorgeous. Like Sinatra she was a big drinker, hated to sleep, loved sex, and had a hair-trigger temper.

Their attraction for each other, to each other, was like the proverbial thunderbolt. They were never going to be the couple who would settle down behind the picket fence and raise babies. They would have these furniture-smashing fights, they would have fantastic make-up sex, then they would start fighting all over again. They were both far too promiscuous by nature ever to be monogamous. Even as they were having this affair of the century—they married in 1951; it was his second marriage, her third—they were constantly having romances behind each other’s back.

Gardner finally decided she couldn’t stand it anymore. One of the most difficult things for her was that from the moment they got together, Sinatra’s career, for various reasons, started going straight downhill. By the time they got married, it was almost over. He had been dropped by his movie studio (MGM), his record label (Columbia), and his agents. The IRS was after him, he was broke, and he was infamous all across America, not only for deserting his wife and kids, but because of his pull toward the Mafia.

DL: Let’s talk a little bit about his movie career. In 1944, he signed with the biggest studio in Hollywood, MGM.

JK: Yes, but just months earlier he had signed a contract with RKO, which he ripped up. Sinatra never saw a contract he didn’t mind ripping up if it suited his convenience. He knew that being a movie star for MGM was a great way to promote his career and fame. It was very important to his financial health. Yet he began to chafe immediately against making musicals for Metro. He didn’t like wearing a sailor suit and dancing next to Gene Kelly, who was an infinitely better dancer than Sinatra was. He didn’t like getting second billing to Kelly.

Sinatra loved making records and he would take as long as it took to make a great one. In the recording studio he would do 22 takes if that’s what was necessary to make the song perfect. But being on a movie set went against all his instincts—it was dreadfully slow and boring. He quickly gained a reputation as an actor who would only do one take. And Hollywood didn’t like that. So even as his fame was cresting in the early- and mid-1940s, his movie trajectory was sort of wavering before it began to sputter and go down.

DL: Near the end of your book, Sinatra’s career starts coming back when he gets a part in the film From Here to Eternity.

JK: Sinatra got the part in the film largely through Ava Gardner and through his own hard work. He was obsessed with James Jones’s big novel From Here to Eternity from the moment it came out in 1951. The book, set in pre-World War II Hawaii and telling the story of how unprepared the American army was for Pearl Harbor, was a big best seller. And Columbia Pictures optioned it immediately, for $85,000, which in those days was a fortune.

At the time, Columbia was run by Harry Cohn, who was a terrible man but a brilliant movie executive. Cohn put together a great production team, consisting of director Fred Zinnemann, screenwriter Daniel Taradash, and producer Buddy Adler. And right away, Cohn and the production team started getting telegrams from Frank Sinatra.

One of the main characters in From Here to Eternity was Private Angelo Maggio, a tough little Italian American from Brooklyn with a big chip on his shoulder. Maggio was one of the world’s victims. And Sinatra, feeling very victimized himself at the time, thought, “This is me. Angelo Maggio and I are the same person; this is my role.” And the telegrams he sent to Harry Cohn and the production team, which told how much he wanted the part, were all signed Maggio.

Ava Gardner’s movie career was rising as fast as Sinatra’s career was falling. But though she was tiring of him and his failures, she still loved him and knew how much he wanted this role. She went to Harry Cohn and told him that she would give him a free movie if he would give Sinatra a screen test. Cohn looked this magnificent woman up and down and wondered what else he might get for free. He gave Sinatra the screen test, and Sinatra aced it.

Eli Wallach was also up for that role and did a terrific screen test, but Wallach had a Broadway conflict and his agents were asking for a lot of money. Sinatra was so desperate, he told Cohn he would do the picture for expenses only, something south of $10,000, which was nothing. Cohn, who was an incredible cheapskate along with everything else, thought, “Okay, here’s my guy. I thought he was just a singer and dancer in MGM movies. Even though he’s down on his luck and his career is nowhere, he’s done this amazing screen test, and he’s offering to work for nothing.” So Cohn cast him, and it rescued Sinatra’s career. He won the Oscar for best supporting actor for playing Maggio.

DL: Would you comment on Sinatra’s musical comeback, which ends your book on a high note?

JK: Sinatra was dropped by Columbia Records in 1952. Then in early 1953, a brilliant and far-sighted young executive at Capitol Records named Alan Livingston decided to sign Sinatra, who at that point was worth nothing on the open market. When Livingston announced to his sales force at a big meeting that he had just signed Sinatra (for something like $200), every man in the room groaned. But Livingston had a vision for Sinatra. He had this genius arranger named Nelson Riddle working for him, and he had this idea of putting Riddle together with Sinatra. The rest is history.

Riddle was deeply, classically grounded. He loved the French impressionist composers. He could put all kinds of tones and colors into an arrangement that nobody else was capable of, and also make it very upbeat if the song called for it. He and Sinatra made this incredible series of genius albums for Capitol throughout the 1950s. In April 1953, just after Sinatra had signed with Capitol, he recorded “I’ve Got the World on a String,” with a gorgeous Riddle arrangement. After the final take, the take that nailed it—and you can listen to it today, it’s just an incredible piece of music—Sinatra yelled out in Capitol Studio A in Los Angeles, “I’m back baby, I’m back.” And he was, he was back.

Download a PDF of the complete article HERE 

David Low '76 writes about arts and culture for the Wesleyan magazine and Wesleyan Connection. He is associate director of publications in the Office of University Communications. He is also a published fiction writer. E-mail: