Why Sinatra Matters (10 page)

“You can’t imagine now how big Crosby was,” Sinatra said in the 1970s. “He was the biggest thing in the country. On records.
On the radio. In the movies. Everybody wanted to be Bing Crosby, including me.”

Crosby did understand the microphone – and the camera. He knew he didn’t have to hit the second balcony with the belting style
forced upon Broadway singers. The microphone permitted a more intimate connection with the audience. He didn’t have to italicize
his acting in movies, the way theater-trained actors did; the close-up allowed him to be natural. Crosby was relaxed, casual,
and very American.

The story of Sinatra’s inspiration by Crosby has been told in all the biographies: how he would sing along with the records,
and how one night in 1935 he took his best girl, a dark-haired beauty named Nancy Barbato, to the Loew’s Journal Square theater
in Newark to see Crosby in a live appearance. On the way home he said to her, “Someday, that’s gonna be me up there.”

Nancy Barbato, the seventeen-year-old daughter of a plastering contractor, was skeptical; on an average Saturday night that
year, about a million young American males must have been saying roughly the same thing. But Frank Sinatra had begun to believe
in his own possibilities. This was America, wasn’t it? And in America anything was possible. So he watched Crosby and listened
to him, simultaneously opening himself to other kinds of music too. Crosby’s stardom obviously inspired Sinatra, but in the
deepest, most substantial ways, his musicianship did not (the truest heirs to the Crosby singing style were Perry Como and
Dean Martin). The most important and enduring influence on the young Frank Sinatra was swing music.

Beginning with Benny Goodman’s breakout in the mid-1930s, and steadily gathering force, this jazz-inspired big band music
was soon cutting across all racial and ethnic lines, becoming
the
music of the generation dominated by the children of immigrants. The growth of radio as a national medium accelerated this
process: white kids could hear Count Basie or Duke Ellington; black kids could listen to Goodman (who included black musicians
Lionel Hampton and Teddy Wilson in the band); kids of all ethnic backgrounds, including Japanese and Mexican Americans, formed
their own swing bands. So although Sinatra was not directly influenced by jazz, he did become the most enduring singer to
emerge from the era of the big bands, which could not have existed without jazz. Their powerful, driving,
confident
sound was emerging at the same time that Sinatra began to sing for audiences.

“I used to sing in social clubs and things like that,” he told the British writer Robin Douglas-Home in 1961. “We had a small
group. But it was when I left home for New York that I started singing serious. I was seventeen then, and I went around New
York singing with little groups in roadhouses. The word would get around that there was a kid in the neighborhood who could
sing. Many’s the time I worked all night for nothing. Or maybe I’d sing for a sandwich or cigarettes – all night for three
packs. But I worked on one basic theory – stay active, get as much practice as you can.”

The family resisted. Marty was furious when Frank dropped out of high school in his senior year. He predicted that his son
would be a bum. Dolly once threw a shoe at him in his room, expressing contempt for his dreamy ambitions; the shoe hit a photograph
of Bing Crosby. Such reactions were not unique to the Sinatra family; many immigrant Catholic families discouraged the artistic
ambitions of their children, for decent reasons: they did not want them to be disappointed and hurt. It was safer to take
the cop’s test or acquire a real trade. Among the Irish, we called this the Green Ceiling; it was enforced by the question,
Who do you think you are?

When it was clear that her son was serious, Dolly gave in, paying $65 to get him a sound system that included a microphone.
This was the equivalent of buying a trumpet for Miles Davis. Frank Sinatra had his instrument at last. Almost immediately,
the gear made it easier for him to find places to play: amateur contests, bars, high school graduations. The Sinatra legend
includes the tale of the formation of the Hoboken Four, winning first prize in 1935 on a popular radio show called
Major Bowes’ Original Amateur Hour
. The winning group went off together on a Major Bowes tour. For the first time, Sinatra was being paid to sing. He and the
rest of the group cut up $75 a week.

“We had turned pro,” he said later. “Bowes was the cheapest son of a bitch in America, and a lowlife besides, but we were
singing for money.”

With Major Bowes in command, the Hoboken Four traveled all the way to California, an enormous journey for kids whose world
until then had been limited to Atlantic City to the south, New York across the water, and the towns and roads of northern
New Jersey. Frank Sinatra was seeing America, which until then was something he had only read about or had seen in the movies.
And he was hearing swing bands on the radios in every town.

“A lot of it was crummy hotel rooms, buses, and trains,” he said later. “But still, you saw how goddamned
big
the country was. And you could hear the same music everywhere. Bing, of course. But also Benny Goodman, Tommy Dorsey. You
heard them more than you ever heard the national anthem.
They
were America.”

The Hoboken Four did not survive the journey; they broke up soon after their return. But Frank Sinatra kept moving, working
part-time as a plasterer (for Nancy’s father), unloading crates of books for a wholesaler, catching rivets in a shipyard,
ending up in 1937 as a singing waiter in a place called the Rustic Cabin in Englewood, directly across the Hudson River from
midtown Manhattan. The pay was $15 a week, plus tips, but the newly completed George Washington Bridge led right over the
river to Manhattan, the city of dreams.

The management could not afford a big band to play the music the rest of America was hearing. But Frank Sinatra was singing.
Those who later claimed to have seen him at the Rustic Cabin could fill Yankee Stadium. But one who did see him was the trumpet
player Harry James, who had just formed his own swing band after leaving Benny Goodman. He needed a boy singer. James heard
Sinatra singing on one of the many radio shows that used him, unsponsored programs for which the singer was not paid (or,
received 75 cents a performance). He decided to drive over to the Rustic Cabin for a look. Among other songs, Sinatra performed
his version of “Begin the Beguine,” a big hit for Artie Shaw. James was impressed, explaining later, “I liked Frank’s way
of talking a lyric.” He gave Sinatra the job. That was the turning point, and without changing his name to Frankie Satin,
the young man was on his way.

A few months earlier, on February 4, 1939, he had celebrated a raise from the Rustic Cabin to $25 a week by marrying Nancy
Barbato in Our Lady of Sorrows in Jersey City. They moved into an apartment on Audubon Avenue in the same city. Frank Sinatra
would never live in Hoboken again.

Now earning $75 a week, Sinatra took Nancy on the road with the Harry James orchestra. Every night he would hear James play
“You Made Me Love You,” his big hit with Goodman. Every night he would listen to swing music that ripped and roared, a rallying
music in a bad time, and then ask questions of the musicians. How did
that
sound happen? On this record, what is
this
instrument? He was acquiring theory and practice.

The young musicians in the James band traveled all over the country, doing one-night stands, eating poorly, sleeping on buses,
sometimes even returning to New York for gigs at Roseland. By all accounts, Frank Sinatra was a happy young man. He had found
the family he was looking for, with his wife at the center. It was a family of men bound together by music, with ambitions
far beyond the narrow goals of the streets of Hoboken. Nobody in this itinerant family dreamed of gaining lifetime employment
in a shipyard or joining a New Jersey fire department.

“With Harry, for the first time in my life I was with people who thought the sky was the limit,” he said to me later. “They
thought they could go to the top, and that’s what they aimed for. They didn’t all make it, but what the hell. They knew the
only direction was up.”

On July 13, 1939, he went into a recording studio for the first time and made two recordings with the James band: “From the
Bottom of My Heart” and “Melancholy Mood.” A month later he recorded “My Buddy” and “It’s Funny to Everyone but Me.” Then
in September he recorded “Here Comes the Night” and a song by Jack Lawrence and Arthur Altman called “All or Nothing at All.”
The first release of the last song sold 8,000 copies. A few years later, after he was established as a star, it would be re-released
during a musicians’ strike and sell a million. On the earliest recorded vocals with the James band, Sinatra sounds uncertain,
unformed, but he does have a distinctive voice. It is certainly not another imitation of Crosby. But on each succeeding date,
he gets closer to what he will become, expressing the feeling of loneliness in a new way, within the context of a modern swing
band. Those earliest records are like talented first drafts of a good first novel.

Near the end of the year, after only six months with James, Sinatra got an even bigger break: Tommy Dorsey came calling. The
Dorsey orchestra was considered the smartest, toughest, hippest of the white swing bands. Some made the same case for Goodman,
of course, calling him the King of Swing, but the argument for the Dorsey band was based on its flexibility. Both could do
pulsing, vibrant, riff-driven swing pieces; Dorsey could also handle smooth ballads, which Goodman did not do well. (Most
musicians of the era thought that the Glenn Miller sound was safe, mechanical, corny.) Dorsey was himself a fine trombone
player, in a sweet legato style; he employed first-rate arrangers, such as Sy Oliver (from the Jimmie Lunceford band), Axel
Stordahl, Bill Fine-gan, and Paul Weston, and superb musicians, including the trumpet player Bunny Berigan, whose talent was
legendary but who would soon be destroyed by alcohol. Sinatra had inadvertently auditioned for Dorsey several years before
he landed the job with Harry James. He showed up to audition for a swing band led by a man named Bob Chester. He later told
Douglas-Home what followed:

“I had the words on the paper there in front of me and was just going to sing when the door opened and someone near me said,
‘Hey, that’s Tommy Dorsey!’ He was like a god, you know. We were all in awe of him in the music business. Anyway, I just cut
out completely – dead. The words were there in front of me, but I could only mouth air. Not a sound came out. It was terrible.”

Sinatra didn’t get the job with Bob Chester. But near the end of 1939 Tommy Dorsey’s star vocalist, Jack Leonard, quit after
a dispute, went off on his own, did poorly, and was eventually drafted. The war in Europe was already four months old, tensions
were increasing in the western Pacific, and the United States was getting ready for its own inevitable entry into the war,
twenty years after young Frank Sinatra saw those triumphant victory parades in Hoboken. Dorsey had heard the Harry James records
(Jack Leonard, in fact, had played “All or Nothing at All” for him) and sent for Sinatra.

“The first thing he said was, ‘Yes, I remember that day when you couldn’t get out those words.’”

Dorsey signed him to a long-term contract for $125 a week, which Sinatra needed since Nancy was now pregnant with their first
child. But it wasn’t easy to leave Harry James. The handsome, mustached trumpet player also had a contract with Sinatra, but
he was a decent man; he knew his own band wasn’t making money and that Dorsey, a “rich” band, could pay the young singer steadily
and well. He tore up his contract and wished Sinatra all the luck in the world. They were still friends when James died in
1983.

“That night the bus pulled out with the rest of the boys at about half-past midnight,” Sinatra later told Douglas-Home. “I’d
said goodbye to them all, and it was snowing, I remember. There was nobody around and I stood alone with my suitcase in the
snow and watched the taillights disappear. Then the tears started and I tried to run after the bus.”

He didn’t catch it. The James band went to play a gig in Hartford, and Sinatra took a train to New York. From there he went
off to three years of school at Dorsey University. Every night he listened to, and learned from, some of the best musicians
in the country: pianist Joe Bushkin, drummer Buddy Rich, Berigan and his replacement as lead trumpet, Ziggy Elman (a defector
from the Goodman band). Sy Oliver taught Sinatra how to ride or glide over the rhythm base of a tune, not repeat it in his
vocals, which was a kind of musical redundancy. Like Sinatra, these musicians had all been formed by Prohibition and the Depression,
and the new vocalist liked their style. They were hard-drinking, tough-talking, and dedicated to the music. They smoked cigarettes.
They chased women. They gambled. They cursed. And they played at the top of their talent, or were sent packing by the remorseless
Dorsey.

Sinatra started as one of the Pied Pipers, the band’s singing group, whose female star was Jo Stafford. She later remembered
Sinatra, walking on stage for the first time, as “a very young, slim figure with more hair than he needed. We were all sitting
back – like, ‘Oh, yeah, who are you?’ Then he began to sing.” After four bars Stafford knew that she had better listen closely.
She thought, “Wow!
This
is an absolutely new, unique sound.” As she elaborated later: “Nobody had ever sounded like that. In those days most male
singers’ biggest thing was to try and sound as much like Bing as possible. Well, he didn’t sound anything like Bing. He didn’t
sound like anybody else that I had ever heard.”

Sinatra swiftly gained the respect of the other members of the band, even those who were friends of the departed Jack Leonard.
He had a variety of troubles with Buddy Rich, a loner who considered himself the band’s feature attraction, with some reason
(many consider him the greatest white drummer of the century). Sinatra even heaved a water pitcher at Rich backstage, sending
shards of broken glass scattering and splashing Stafford. But they were also friends, rooming together on the road, where
Sinatra would absorb Rich’s knowledge of rhythm and tempo. As his confidence grew, Sinatra strengthened and refined his technique
by listening to all the musicians, but above all to Dorsey. And he made records with the band. The first two were recorded
on February 1, 1940 (“The Sky Fell Down” and “Too Romantic”); eighty-one others would follow.