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I am pleased to offer this free excerpt from my award-winning Sinatra biography, Cent'Anni: The Sinatra Legend at 100.

Understanding the Frank Sinatra phenomenon, even now—100 years, or cent' anni, after his birth, remains an elusive goal, because there were so many renditions of the man, so many different Frank Sinatras.

Four years after Sinatra won a well-deserved Oscar for Best Supporting Actor, in 1953, for his portrayal of Army Private Angelo Maggio in From Here to Eternity, Joanne Woodward received the Oscar for Best Actress for her role in The Three Faces of Eve, based on a true story about a woman with multiple personalities. Just three of those personalities appeared in the motion picture, but the actual patient exhibited signs of 22 different women inhabiting her. I don't suggest that Frank Sinatra suffered from a mental disorder, or that the various aspects of his personality and character were blocked from his consciousness. There's no doubt about one thing, however. These diverse facets of the man—some brilliant in their eye-catching allure and some darkly flawed and foreboding, best kept from public view—tell a story of the most fascinating entertainer of the twentieth century.

The Sinatra beloved by millions of fans—the bobby-soxer heartthrob of the 1940s, before becoming "The Voice" and, later, "The Chairman of the Board" and "Ol' Blue Eyes"—is the well-known version and, probably, the easiest to like. Writer John McPhee, in a piece for The New Yorker, introduced me, fittingly, to an obscure Italian word that may offer the best description of this particular Frank Sinatra.

The word is sprezzatura, coined by Baldassare Castiglione, a formidable author, diplomat and courtier among the city-states of Renaissance Italy. McPhee, with the help of one of his Princeton University students and a daughter residing in Italy, defined the term thusly: "effortless grace, all easy, doing something cool without apparent effort" and having "nonchalance," although the latter word implies an indifference or lack of warmth, attributes entirely absent from and opposite to the unique way Sinatra delivered the lyrics of just about every song he sang, over a career spanning 60 years.

There are offshoots of this user-friendly image of Frank Sinatra. He could be tremendously generous and compassionate, quick to assist performers down on their luck and, in some instances, complete strangers in the throes of misfortune. Watching television one night with his daughter Tina, Sinatra saw a news clip about an impoverished family that had just lost everything as a result of a Christmas tree fire. Sinatra picked up a phone and called an employee, telling him to "send them a nickel"—Sinatra parlance for $5,000.

Buddy Rich, the flashy drummer Sinatra often feuded with, like cock roosters in a barnyard turf war, when the two worked together in Tommy Dorsey's band, battled illness and financial turmoil through much of his professional life. During one such period, Sinatra paid for Rich's hospital bills. In another, when Rich visited Sinatra backstage after a concert and talked about forming a band, Sinatra wrote him a check for $25,000 on the spot to help him get started.

When Sammy Davis, Jr., then part of a minor Las Vegas act called the Will Mastin Trio, lost an eye in a terrible car crash, in November 1954, the young entertainer was despondent. Dancing was a big part of his performing life, and he worried that with one eye, he'd never be able to regain the balance that enabled him to execute his intricate routines. Sinatra visited Davis in his hospital room and hugged the sobbing young man.

"You're gonna be fine," Sinatra said. "Charlie [a favorite Sinatra nickname for his pals], you gotta be strong. You'll come out of this thing bigger than ever. You're alive, man. You're alive."

Sinatra took Sammy under his wing, brought him to his Palm Springs home to recuperate, then took him to his mother's house in New Jersey for an Italian dinner. When Davis was fully recovered, Sinatra helped get him a booking at Ciro's, a Hollywood club, and packed the room with a star-studded audience, including Bogart and Bacall, James Cagney, Cary Grant, Edward G. Robinson, and Spencer Tracy. They gave Sammy a thunderous reception. Sinatra was right—Davis did become "bigger than ever."

Frank Sinatra was a fierce champion of racial equality and an implacable foe of intolerance, at a time when there was a risk to such advocacy, especially for an entertainer. In 1945, he made a film short for RKO Studios called, The House I Live In. In it, Sinatra, already a big star, talked to a gang of boys about showing respect and understanding toward those with different religious backgrounds. The film short received a special Academy Award, and Sinatra got a standing ovation from the Hollywood crowd when he accepted it. On October 23, 1945, he went to Benjamin Franklin High School in Harlem to plead for racial tolerance and to help quell violence that had erupted between Italian-American and African-American students. In November, he went on a similar mission to Gary, Indiana, where he told students, "I can lick any son-of-a-bitch in the joint." His attempt to connect with the students on their level was unsuccessful—they just wanted to hear him sing. But, he made the attempt, which was more than other entertainers were doing.

Sinatra's work in this regard also brought him unwanted scrutiny from those who were trying to tie him to the Communist Party in America. The Federal Bureau of Investigation maintained a file on the singer, but was never able to plausibly connect Sinatra to the Communist Party or to any of its front organizations. Sinatra was left-leaning during the 1940s, certainly, but a Commie? Never.

Up to the early 1960s, the entertainment business was still segregated in many of its venues, including Las Vegas. Black performers often could not occupy the rooms, guest elevators or restaurants in the very hotels in which they were performing or even join the white folks in losing money in the casinos. Sinatra fought that mindset wherever he performed, using his celebrity as clout and insisting on equal treatment for every black member of his entourage. While on tour later in his career, Sinatra was still sensitive to racial issues. At one concert, he saw that the musicians hired for the event were predominantly white—there were just three black faces among the 40 members of the orchestra.

"What the fuck is this snow white orchestra you got here?" Sinatra demanded of the concert promoter, who replied that it was too late to change, that it would be too expensive.

"I want at least 30-percent black musicians," Sinatra ordered. Later, when Sinatra returned to the concert hall for rehearsal, the orchestra included 15 black musicians.

For every admirable trait that Sinatra exhibited over his lifetime, there seemed to be a more sinister, less appealing flip side. Sincere in his attitude toward race and religion, Sinatra would nevertheless pepper his nightclub act with ethnic slurs, drawing laughs from the audiences of the 1950s, -60s and -70s. Sammy Davis, Jr. was a favorite target at gatherings of the Rat Pack "Summit" in the early 1960s, when Dean Martin and Peter Lawford joined in the "fun." Sinatra's nickname for his personal valet, a black man he paid very well and seemed genuinely affectionate toward, was "spook." Some of the epithets he delivered offstage, among cronies, were even more egregious, especially when he was drunk or sensed a breach of loyalty.

During World War II, Sinatra appeared regularly at bond rallies in the States and made musical recordings, called V-Discs, for the servicemen fighting around the globe, but he never went near a war zone to entertain them, as did Bob Hope, Bing Crosby, Phil Silvers and dozens of other male and female Hollywood stars, at great risk to their safety. It wasn't until May and June of 1945, after the shooting in Europe had ended, that Sinatra performed for troops still stationed in Italy. And even then, he damaged his image by making a fuss over the hotel accommodations the Army had arranged for his troupe in war-torn Rome—they weren't grand enough. Sinatra was classified 4-F during the war, but many considered that to be a manufactured arrangement to keep him out of uniform. It was not, according to a secret F.B.I. investigation, which didn't become public until many years later.

Sinatra was adored by millions of women, yet he was an unfaithful husband, to put it mildly, and an absent father. George Jacobs, his valet for 15 years, called him "the best telephone father there ever was." He could lavish attention and expensive gifts on the woman of the moment, then drop her with little or no explanation. Lauren Bacall found that out soon after Sinatra took up with her.

In the 1950s, Frank was close friends with Humphrey Bogart and his wife, Lauren Bacall, leaders of the Holmby Hills Rat Pack, a group of celebrities who gathered periodically in the Bogart home, in an elite area of Los Angeles that gave this group its name, to drink, play silly practical jokes on one another, exchange civilized witticisms, and revel in each other's company—sort of an Algonquin Round Table-West, though less literary. Bacall, who was the first to use the term "rat pack," described membership criteria this way: "One had to be addicted to non-conformity, staying up late, drinking, laughing, and not caring what anyone said or thought about us." Among the charter members were Spencer Tracy and Katherine Hepburn, David Niven and his wife, restaurateur Mike Romanoff, Judy Garland and husband Sid Luft, screenwriter Nunnally Johnson and Hollywood agent Irving "Swifty" Lazar.

Sinatra, who idolized Bogart and Spencer Tracy, drifted into the group's orbit in 1952, in the pre-From Here to Eternity days, during an estrangement from second wife Ava Gardner. "He was alone and not happy," Bacall recalled, "neither work nor his personal life had been going well."

Throughout Bogart's career, the tough-guy actor had a cigarette dangling from his mouth in just about every movie scene. More than an actor's prop, it was a hard-drinking, chain-smoking lifestyle that caught up with Bogie in 1956, when he was diagnosed with cancer of the esophagus. As Bogart's condition worsened, Frank Sinatra was frequently on hand to comfort "Betty"—Lauren Bacall's real name and the one all her friends used—and help her through the hard times. One observer said that Frank and Betty became intimate even before Bogart passed, but soon afterwards, their relationship went public. They made plans to marry, which someone—Bacall or a friend—leaked to gossip columnist Louella Parsons. Sinatra was furious and broke off the engagement with a brief phone call. And then he simply stopped talking to his former fiancée . . . for six years.

Drunk or sober, but mostly drunk, Sinatra could be the nastiest, most ill-tempered person to be around. He would pick a fight at the slightest provocation, often using a chair or other handy object as a weapon or projectile. He once drove a golf cart into a plate glass window at the Sands Hotel in Las Vegas, with his third wife, actress Mia Farrow, seated beside him, because of a perceived slight by a Sands executive inside the casino. He then piled chairs together and tried to set them on fire with his cigarette lighter. Fortunately, no one was seriously injured.

Standing just five feet, seven and a half inches tall, when not in elevator shoes, and weighing about 120 pounds for most of his adult life, Sinatra's muscle power and pugilistic skills did not always rise to the occasion, despite early publicity shots at Stillman's Gym in New York City showing him attired in boxing trunks and gloves. No matter—the singer always had several brawny bodyguards in his entourage, including his friend Jilly Rizzo and road manager Hank Sanicola, ready to finish whatever physical altercation their boss started.

Performance contracts never meant much to Frank Sinatra, even as a singer in the Harry James band. Seven months after James discovered the 23-year-old at the Rustic Cabin, a roadhouse in Englewood Cliffs, New Jersey, and signed him to a two-year contract, rival-bandleader Tommy Dorsey offered him $50 a week more and greater national exposure. Sinatra asked the lesser known James to be let out of his contract, and James goodheartedly acceded to his singer's wishes, not wanting to stand in the way of a kid he recognized as a future star. Sinatra would later quit the Dorsey band, in 1942, to go out as a solo act, but that broken contract proved more costly to the singer and fueled speculation about Mafia-style tactics used to persuade Dorsey to let him go.

Willie Moretti, a North Jersey crime boss and Hasbrouck Heights neighbor to the young Sinatra family (wife Nancy, two-year old Nancy Jr., and the Voice, himself) in the early 1940s, bragged to one intimate about his role in getting Dorsey to release Sinatra from his contract. Dan Lewis, entertainment editor for the Bergen Evening Record in the 1940s, once asked his gangster-friend Moretti about those rumors—years later, but before Moretti was gunned down in a Cliffside Park, New Jersey restaurant in October 1951 by confederates of Albert Anastasia, head of Murder, Inc., the Mafia's enforcement arm.

"Well, Dan" Moretti told Lewis, "let's just say we took very good care of Sinatra." Moretti didn't elaborate on who the "we" was meant to represent in that statement, but no elaboration was necessary.

Sinatra's mob connections may actually have started when he was a youth in Hoboken, his birthplace. Dolly and Marty Sinatra, Frank's parents, owned a saloon in Hoboken during Prohibition, where young Frankie first began singing in front of an audience, on a table-top in his father's bar. Waxey Gordon, one of the area's top bootleggers, was a bar patron and, most likely, its liquor supplier. Frank's paternal grandfather came from the same village in Sicily that gave us Salvatore Lucania, better known as Lucky Luciano—someone Frank Sinatra would rub elbows with at various intervals during his career, along with a Who's Who-worthy list of organized crime figures that, besides Luciano and Moretti, included Meyer Lansky, Benjamin "Bugsy" Siegel, Frank Costello, Sam "Momo" Giancana, Joe Fischetti, Johnny Roselli, Carlo Gambino, Abner "Longy" Zwillman, Vito Genovese and Angelo "Gyp" De Carlo, who was related to the Sinatra family through marriage.

Confidential sources once told law enforcement officials that Sinatra was a bagman for Luciano, delivering millions in cash to the exiled mobster in Cuba and Italy on three separate occasions. F.B.I. files offered no corroboration for those claims, which Sinatra vehemently denied. But comedian Jerry Lewis made a similar assertion. He said that Sinatra almost got caught while carrying $3.5 million in cash through U.S. Customs in New York, information he could only have gotten from Sinatra, or someone close to him. Obviously, there was insufficient evidence to warrant prosecution, but the taint of mob association plagued Sinatra, fairly or unfairly, throughout his career.

The most famous manifestation of that rumor-filled, gossip-fed association, of course, was the Johnny Fontane character in Mario Puzo's The Godfather and in the motion picture of the same name. Fontane got a career-changing role in a movie—read, Private Angelo Maggio in From Here to Eternity—when his godfather, Don Vito Corleone, arranged to have a Sicilian calling card, in the form of a horse's head, placed in the fictional movie producer's bed. Mario Puzo, for the rest of his life, would deny any connection between characters in his book and Frank Sinatra, but that didn't stop Sinatra's wrath from being visited upon the author when they ran into each other. It didn't help that Puzo's fictional godfather was said to be based, in part, on real-life Mafia boss Frank Costello, one of Sinatra's principal mob benefactors. But Sinatra had another benefactor, one more important than any mobster.

Dolly Sinatra was clearly the driving force in the family, a not uncommon occurrence in the often matriarchal Italian culture. Her influence on Sinatra's life and career cannot be overestimated. James Farina, City Clerk of Hoboken for the past 31 years, knew Dolly and called her "the engine that drove Frank Sinatra." She was feisty, foul-mouthed, smart, ambitious, conniving, ruthless, and demanding—in short, all the traits one finds in her son and only child, the very essence, aside from his natural talent, of what made Sinatra Sinatra.

What was it, then, about Frank Sinatra? His beginnings hardly presaged the success he would later achieve. As a teenager, he'd sometimes burst into song, uninvited, at neighborhood gatherings, only to be viewed as a pest. Older boys once tossed him and his ukulele (the do-it-yourself accompaniment of the day) out of a pool hall, so they wouldn't have their game disturbed. Frankie persisted, though, singing at every social club and church-basement dance that would have him, mostly for no payment. At first, he used a megaphone to project his voice, in the style of earlier singing sensation Rudy Vallee, but it wasn't a device that suited the young man's thin, reedy voice. After Dolly finally accepted that her son wouldn't be happy with any career choice but singing, she bought him a $65 microphone and public address system, which set Frankie apart from other local singers. It got him more gigs and more experience—exactly what he needed.

At 19, Sinatra sang as part of the Hoboken Four, contestants on Major Edward Bowes's Amateur Hour, a top radio show in the 1930s. The group was hastily formed by the Major, himself, after Frank and a Hoboken trio, the Three Flashes, had auditioned. Bowes introduced them as the "singing and dancing fools." They actually won that competition and went on to tour, briefly, with one of Bowes's theatrical groups. It didn't last, and Frank returned home, undeterred but with no prospects.

The ultimate goal for a singer in those days was to become part of an established band, as the featured vocal artist. But few professionals paid Sinatra much attention back then, despite his efforts at self-promotion. He even had the effrontery to approach bandleader Glenn Miller to ask for a job, but Miller turned him down. Sinatra, at the time, had no formal training as a singer, although he would later hire a voice coach for a short while, at a dollar per lesson. His politically connected mother called in favors to get her Frankie his first paid singing jobs as a solo performer, at a local Hoboken club and at the Rustic Cabin, where he had to do double-duty as a waiter when not on stage. The log cabin-styled roadhouse was a popular watering hole for travelers going to and from New York City, including an occasional celebrity.

One night, while Sinatra was performing at the Rustic Cabin, a musician in the band told him that songwriter Cole Porter was in the audience—the music genius who practically wrote the American songbook on his own. Sinatra dedicated his next number to Porter, but was so nervous he forgot the lyrics to a song he had sung many times, Porter's own "Night and Day."

Tommy Dorsey was also unimpressed the first time he heard Sinatra sing, or, as it turned out, not sing. Sinatra was auditioning in Manhattan for a job with Bob Chester's band, when Dorsey, a friend of Chester's, walked into the studio to watch. "We were all in awe of him in the music business," Sinatra would tell biographer Robin Douglas-Home in the early 1960s. Just 22 or 23 at the time of the Chester audition, Sinatra froze when he saw Dorsey. "Not a sound came out," he later recalled. "It was terrible." Dorsey teased Sinatra about it a year later, after Dorsey had recognized the younger man's talent and installed him as his own "boy singer," as male band singers were called in those days.

Before the Dorsey job, though, there was bandleader Harry James, who hired Sinatra away from the Rustic Cabin in June 1939, at $75 a week—a good salary when the average family breadwinner, if lucky enough to have a job, was bringing home $25 a week. It was Sinatra's first big break. That same year, James commented about his new singer to a reporter from DownBeat, one of the music industry's top magazines.

"He considers himself the greatest vocalist in the business," James said. "Get that! No one ever heard of him. He's never had a hit record. He looks like a wet rag. But he says he's the greatest."

Harry James's characterization was right on the money. He'd also hit upon the secret to the legend that Frank Sinatra became, which can be summed up in one word: attitude. Sinatra possessed unshakeable confidence in himself and faith in his ultimate rise to the heights of the entertainment world—it showed in every performance he gave. He was the original Jersey boy, if you will. People in a position to help liked his cockiness, and so did audiences.

It was an attitude forged in the rough-and-tumble world of the entertainment industry, by way of Hoboken, New Jersey.

Copyright © 2018 by Richard Muti. All rights reserved for all content published on this website.