The Sinatra files_ the secret FBI Dossier Part 1

The Sinatra files.

The secret FBI dossier.

by Tom Kuntz & Phil Kuntz.

Introduction.

When he died on May 14, 1998, Frank Sinatra was one of the most chronicled celebrities of modern times-the focus of oceans of ink and miles of film and video footage at turns serious-minded, celebratory, or mean-spirited.

But one detailed record of his life, taken from a uniquely penetrating perspective, became fully public only after his death: the Federal Bureau of Investigation's extensive files on the singer and screen star. Most were compiled over the course of several decades under the watchful eyes of J. Edgar Hoover, as his agents investigated whether Sinatra was a draft-dodger, a Communist, or a front for organized criminals.

Released in December 1998 in response to requests under the Freedom of Information Act, the 1,275-page dossier is a trove of insights into Sinatra's life, his turbulent times, and, perhaps most important, the Hoover-era FBI's invasive and at times almost voyeuristic ways.

Although Hoover's FBI kept files on other celebrities, few were as voluminous, for no other subject was as enduring or controversial. For more than five decades, Sinatra was a major force in American society and popular culture, a politically active, hard-partying star who a.s.sociated with powerful figures in both the underworld and at the highest levels of government through every important turn in the latter half of the twentieth century. The Sinatra FBI files offer themselves as an allegory of the American Century and its obsessions.

Extensive excerpts from them are published here for the first time. Along with a limited number of historical doc.u.ments from other sources, the files have been organized and supplemented with explanatory notes to put them in context and to highlight their revelations.

Taken together, they invite a rea.s.sessment of the entertainer. Revelations abound. chapter 1 chapter 1 details how the rail-thin crooner with impeccable phrasing at first told World War II draft board officials that he had no physical or mental disabilities, then a.s.serted later not only that he had a perforated eardrum, which was true, but also an irrational fear of crowds, which was highly doubtful. With a blossoming career at stake, could Sinatra have been feigning mental illness? details how the rail-thin crooner with impeccable phrasing at first told World War II draft board officials that he had no physical or mental disabilities, then a.s.serted later not only that he had a perforated eardrum, which was true, but also an irrational fear of crowds, which was highly doubtful. With a blossoming career at stake, could Sinatra have been feigning mental illness? chapter 2 chapter 2 includes evidence suggesting an unholy alliance between press muckrakers and the FBI's star-obsessed top bra.s.s, who occasionally helped favored journalists seeking dirt on Sinatra. This new material lends credence to Sinatra's lifelong grudge against the press. includes evidence suggesting an unholy alliance between press muckrakers and the FBI's star-obsessed top bra.s.s, who occasionally helped favored journalists seeking dirt on Sinatra. This new material lends credence to Sinatra's lifelong grudge against the press.

chapter 3 offers a disturbing glimpse into the red-baiting 1940s and 1950s, when Sinatra was unjustifiably, in his words, "tagged [as a] commie." Though for a time he stood by other embattled Hollywood stars caught up in the paranoia, he became so sensitive to the charges that, according to an intermediary, he volunteered to become an undercover snitch in the FBI's hunt for subversives. Hoover turned him down. So did the army years later, when Sinatra offered to entertain American troops in Korea. offers a disturbing glimpse into the red-baiting 1940s and 1950s, when Sinatra was unjustifiably, in his words, "tagged [as a] commie." Though for a time he stood by other embattled Hollywood stars caught up in the paranoia, he became so sensitive to the charges that, according to an intermediary, he volunteered to become an undercover snitch in the FBI's hunt for subversives. Hoover turned him down. So did the army years later, when Sinatra offered to entertain American troops in Korea.

In some key instances, what isn't in the files is as important as what is.

For example, although excerpts in chapter 4 chapter 4 and elsewhere a.s.siduously note Sinatra's interactions with notorious hoodlums, the FBI gathered no evidence that mob pressure landed him his Oscar-winning role as the pugnacious Private Angelo Maggio in and elsewhere a.s.siduously note Sinatra's interactions with notorious hoodlums, the FBI gathered no evidence that mob pressure landed him his Oscar-winning role as the pugnacious Private Angelo Maggio in From Here to Eternity From Here to Eternity in 1953. This canard is so embedded in the popular imagination that it is a.s.sumed to be the inspiration for a scene in in 1953. This canard is so embedded in the popular imagination that it is a.s.sumed to be the inspiration for a scene in The G.o.dfather The G.o.dfather in which a severed horse's head in a movie mogul's bed ensures a plum role for an Italian-American singer. Nor do the files support the widely held a.s.sumption that the mob in 1942 strong-armed Tommy Dorsey into releasing Sinatra from a contract that ent.i.tled the bandleader to 43 percent of the singer's earnings for life. in which a severed horse's head in a movie mogul's bed ensures a plum role for an Italian-American singer. Nor do the files support the widely held a.s.sumption that the mob in 1942 strong-armed Tommy Dorsey into releasing Sinatra from a contract that ent.i.tled the bandleader to 43 percent of the singer's earnings for life.

More broadly, the files offer a striking case study of the way Hoover managed and manipulated the sensitive information at his disposal. chapter 5 chapter 5, 6 6, and 7 7 detail how the FBI director, with little subtlety, made sure each successive politician who befriended the popular singer knew exactly how much derogatory information the FBI had on their friend. detail how the FBI director, with little subtlety, made sure each successive politician who befriended the popular singer knew exactly how much derogatory information the FBI had on their friend.

John F. Kennedy's recklessness is by now well doc.u.mented, but the files' dry bureaucratic account of the president consorting with a.s.sociates of the very mobsters his brother the attorney general was trying to imprison will startle even the best-read Kennedy aficionados.

There also are moments of unintentional humor, as in the case of the straight-faced FBI memo that says, "Sinatra denied he sympathized with Lenin and the Marx brothers." And the capitalized names of Marilyn Monroe, Tony Bennett, and other celebrities leaven the G-men's reports like the boldface type of gossip columns.

The files also shed light on the evolving nature of Sinatra's relationship with the FBI: He eventually joined with his would-be pursuers in the bureau in a mutually respectful common cause, when Sinatra's son was kidnapped in 1963.

In sum, the files track an iconic career whose arc seems to personify postwar America's loss of innocence: Sinatra's evolution from liberal, idealistic crooner to sophisticated, s.e.xually liberated swinger to jaded Las Vegas headliner and friend of Republican presidents.

Was the scrutiny unfair?

The FBI twice seriously considered prosecuting Sinatra, once for denying that he was a Communist and once for denying that he par-tied with a mobster. But despite coast-to-coast investigations, the FBI couldn't make a case against him.

Sinatra's problem throughout his career was that he never did much to remove the taint of guilt by a.s.sociation, especially with the mob. Judged by the company he kept, Sinatra kept inviting more scrutiny. The FBI obliged, and its files grew until the singer became, as the journalist Pete Hamill put it, "the most investigated American performer since John Wilkes Booth."

But in many ways Sinatra wasn't so unique as a subject of FBI interest. The agency kept files on thousands of people, famous and otherwise, whenever they figured in investigations, no matter how tangentially.

According to Hoover's longtime deputy director, Cartha D. "Deke" DeLoach, the main FBI dossier on someone like Sinatra wouldn't have been kept in the agency's collection of "Central Files," which were open to virtually anyone in the bureau. Instead, most of the Sinatra material would have ended up in the "Official and Confidential" files of well-known people, which were located in Hoover's suite in two small filing cabinets behind the desk of his secretary, Helen Gandy.

There was nothing sinister in this, DeLoach maintains. In his 1995 memoir, Hoover's FBI: The Inside Story of Hoover's Trusted Lieutenant Hoover's FBI: The Inside Story of Hoover's Trusted Lieutenant, DeLoach writes: "The purpose of keeping the O&C Files in an area of limited access was to protect the privacy of those about whom information had been gathered, not to maintain secret records for the purpose of blackmail."

Many a Hoover chronicler would disagree with DeLoach about the sanct.i.ty of his boss's motives, but what is undeniable is that the director often took a personal interest in the minutiae of Sinatra's life. Readers of these pages can judge for themselves why.

The FBI began compiling the dossier during one of the most charged moments in American history-the 1940s. From the start of the Second World War, Sinatra's rise to fame stirred an incredible amount of resentment and envy. The crooning heartthrob was thrilling millions of bobby-soxers, and making millions doing it, while avoiding the fate of the hundreds of thousands of other young men who forwent love and fortune to fight European fascism and j.a.panese imperialism.

As Sinatra himself noted, he was a surrogate to young women for "the boy in every corner drugstore who'd gone off, drafted to the war." The popular historian William Manchester put it another way: "I think Frank Sinatra was the most hated man of World War II."

And so, on the heels of pandemonium-filled appearances at New York's Paramount Theatre, a letter arrived at FBI headquarters in Washington. Thus began the FBI's shadow biography of Frank Sinatra on August 13, 1943: A concerned citizen intimated darkly that a "shrill whistling sound" of shrieking bobby-soxers during a recent Sinatra radio broadcast might have been a devious technique "to create another Hitler here in America through the influence of ma.s.s-hysteria!"

Later, an FBI memo said that the columnist Walter Winch.e.l.l gave the bureau a reader's letter a.s.serting that the FBI was investigating whether the singer had bribed his way out of the draft. The FBI wasn't investigating any such thing, but the tip insured that it would. In February 1944, the FBI opened a "limited inquiry" that actually was far-reaching enough to dredge up records of Sinatra's 1938 arrest in New Jersey for an alleged "seduction" under a false promise of marriage-a charge that was later changed to "adultery" after it was discovered that the supposed victim was married. That matter also was dropped, and Sinatra was free to love and leave again.

As World War II ended, Sinatra charmed his fans with songs like "Put Your Dreams Away" and frothy films like Anchors Aweigh Anchors Aweigh, with Frank playing Gene Kelly's wide-eyed, sailor-suited sidekick. But a serious film, all of ten minutes long, proved more important to the young singer's career. His heartfelt plea for racial and religious tolerance in The House I Live In The House I Live In-borne of painful memories of growing up in ethnically divided Hoboken, New Jersey-won a special Academy Award and helped debunk the singer's reputation as a frivolous, draft-dodging crooner.

The film, written by the leftist screenwriter Albert Maltz (later blacklisted), also made Sinatra a darling of the American Left and presaged the star's a.s.sociation with groups the FBI deemed to be Communist fronts. It wasn't long before an informant told the FBI (incorrectly) that Sinatra had "recently been admitted to the New York branch of the Communist Party."

In the conservative press, Sinatra thus became, at best, a Communist-leaning "fellow traveler." In 1946, the far-right radio commentator Gerald L. K. Smith told the House Un-American Activities Committee that Sinatra "has been doing some pretty clever stuff for the Reds," without backing up the charge. The committee never actively pursued Sinatra, but other conservative columnists, like Westbrook Pegler of the Hearst chain's New York Journal-American New York Journal-American and Lee Mortimer of the and Lee Mortimer of the New York Daily Mirror New York Daily Mirror, picked up the red-baiting cudgel against the pro-Roosevelt singer. By 1946, Hoover himself was disdainful, scrawling this unkind comment at the bottom of a memo about Detroit schoolgirls skipping school to see the star: "Sinatra is just as much to blame as are the moronic bobby-soxers."

Later, as the bobby-soxers grew up, Sinatra's career headed into a precipitous decline-marked by a drought of hit singles from 1948 through 1952 and dreadful films like The Kissing Bandit The Kissing Bandit. Sinatra's marriage to Nancy Barbato, whom he wed in 1939, was on the rocks, too, as he pursued affairs with a series of actresses.

Public disaffection increased after the Scripps-Howard columnist Robert Ruark denounced him in February 1947 for having flown to Havana with two members of Al Capone's Chicago gang and socializing there with the deported gangster Lucky Luciano-hard evidence of Sinatra's growing tendency to a.s.sociate with tough guys.

The FBI files soon began detailing Sinatra's mob ties, and his press detractors were in high dudgeon. Mortimer, the Mirror's Mirror's film editor, was relentless, sarcastically opining that film editor, was relentless, sarcastically opining that It Happened in Brooklyn It Happened in Brooklyn "bogs down under the miscast Frank (Lucky) Sinatra, smirking and trying to play a leading man." "bogs down under the miscast Frank (Lucky) Sinatra, smirking and trying to play a leading man."

On April 8, 1947, Sinatra struck back, literally, socking the diminutive Mortimer when they came across each other at Ciro's nightclub in Hollywood. A month later, in one of the FBI files' most telling episodes, Mortimer met with Clyde Tolson, Hoover's right-hand man and best friend, to find out what the bureau had on Sinatra. Tolson informed Hoover by memo that he had told Mortimer he couldn't give him "any official information," yet the memo itself seems to suggest that Tolson had been helpful. Later, Mortimer reported that Sinatra had delivered $2 million in cash to Luciano in his luggage while in Havana. Often repeated, this charge isn't backed up by anything in the FBI files.

By this time, Sinatra's career was going to the dogs: He performed a canine howl on the novelty song "Mama Will Bark." In 1950, Louis B. Mayer had fired him from MGM after the intemperate star had joked too loudly that the mogul's horseback-riding injury actually resulted from falling off his mistress, Ginny Simms.

As if the draft-dodging, commie, and mob allegations weren't enough, Sinatra's marriage collapsed in the midst of a tumultuous affair with his second-wife-to-be, Ava Gardner, during which the singer attempted suicide. Coupled with his mercurial behavior, all this made Sinatra almost radioactive in show business. Performing at the Copacabana in New York while ravaged from stress, The Voice gave out as Sinatra strained to reach a high note during "Bali Hai." He'd suffered a throat hemorrhage.

Sinatra may have been desperate to relieve the pressure. On September 7, 1950, a colleague informed Tolson in a memo that a Sinatra go-between was trying to meet Hoover "with a proposition Sinatra had in mind." Since "subversive elements" with whom Sinatra had been linked "are not sure of his position," the singer "consequently feels that he can be of help as a result by going anywhere the Bureau desires and contacting any of the people from whom he might be able to obtain information." Perhaps wary of Sinatra's sincerity, Tolson scribbled at the bottom, "We want nothing to do with him," to which Hoover added, "I agree."

But Sinatra's career began a phenomenal resurgence in 1953 with his Oscar-winning turn in From Here to Eternity From Here to Eternity. Soon afterward, the singer tried to join a troupe traveling to Korea to entertain soldiers at Christmastime. The army, however, said no, citing his alleged Communist affiliations. Responding to suggestions that the rejection was based on information supplied by the FBI, Hoover's handwritten notation on a memo ordered subordinates to "nail this down promptly."

Agents looked into the matter and later reported on a bizarre meeting in which Sinatra tried to persuade three army generals to let him sing for the troops. One general congratulated Sinatra on his fine performance in From Here to Eternity From Here to Eternity-a movie that was probably more subversive than Sinatra himself ever was, for it was about infidelity, indiscipline, and brutality in the military. "I am just as communistic as the Pope," Sinatra told the generals, to no avail.

Yet the FBI persisted in trying to dig up "subversive information" on Sinatra as agents tried to prove that he lied in denying Communist affiliations to get a pa.s.sport. Finally they gave up, and Hoover concluded in a memo that despite repeated "nonspecific a.s.sociations" of Sinatra's name with the Communist party, "the investigation failed to substantiate any such allegation."

Not that it mattered much. By the mid-1950s, Sinatra was back on top. A collaboration at Capitol Records with the arranger Nelson Riddle was yielding the best work of Sinatra's career, alb.u.ms of swing and sophistication, including In the Wee Small Hours In the Wee Small Hours (1955) and (1955) and Songs for Swingin' Lovers Songs for Swingin' Lovers (1956). He followed his Oscar success with memorable roles in, among other films, (1956). He followed his Oscar success with memorable roles in, among other films, Suddenly Suddenly (1954), in which he played a would-be presidential a.s.sa.s.sin-an eerie foreshadowing of Jack Kennedy's murder. (1954), in which he played a would-be presidential a.s.sa.s.sin-an eerie foreshadowing of Jack Kennedy's murder.

The FBI's interest in Sinatra might have receded but for his mob a.s.sociations, which if anything were growing. In 1954 he had bought a 2 percent stake (later increased) in the Sands Hotel in Las Vegas, which reputedly had mob backers. He was seen with Joe Fischetti, one of the mobsters he had accompanied to Havana, and was especially friendly with Sam "Momo" Giancana, the Chicago mob boss who had interests in many of the clubs where Sinatra had performed.

But what really got the FBI's attention was his growing closeness to the rising young senator from Ma.s.sachusetts who was running for president. Senator John F. Kennedy had even adopted Sinatra's "High Hopes" as his 1960 campaign theme song. Sinatra, for his part, badly wanted a place in Camelot. After hiring Maltz, the screenwriter for The House I Live In The House I Live In, who was now blacklisted, to do a script for another movie, Sinatra bowed to pressure from the Kennedys, first by delaying the news until after the 1960 New Hampshire primary and then jettisoning Maltz altogether.

Hoover received regular reports on all this and more. On March 22, 1960, an informant told the FBI that Confidential Confidential magazine was investigating a rumor that Senator Kennedy had attended "an indiscreet party" at Sinatra's Palm Springs home. Later the FBI noted that Sinatra and Kennedy had partied together in New York, too, and that magazine was investigating a rumor that Senator Kennedy had attended "an indiscreet party" at Sinatra's Palm Springs home. Later the FBI noted that Sinatra and Kennedy had partied together in New York, too, and that Confidential Confidential reportedly had "affidavits from two mulatto prost.i.tutes in New York." In Las Vegas, the FBI heard that "show girls from all over town were running in and out of the senator's suite" and that "Kennedy had been compromised with a woman." reportedly had "affidavits from two mulatto prost.i.tutes in New York." In Las Vegas, the FBI heard that "show girls from all over town were running in and out of the senator's suite" and that "Kennedy had been compromised with a woman."

According to FBI informers, the mob was looking for an in with the next president of the United States. As one memo put it, the mob wanted Sinatra to use his show-biz friendship with Kennedy in-law Peter Lawford to get close to Jack Kennedy "so that Joe Fischetti and other notorious hoodlums"-Sinatra's pals-"could have an entree to the Senator."

After the mob reportedly helped Kennedy win the election, the FBI examined the phone records of one Judith Campbell and discovered that she was mixed up with both the president and Sam Giancana-not to mention Sinatra, who had introduced her to both men on separate occasions. It wasn't hard to figure out that she was the president's lover, as she later acknowledged. In early 1962, Hoover laid out what the FBI knew for Attorney General Robert F. Kennedy, the president's brother. It was a not-so-subtle suggestion that the president's coziness with Sinatra could destroy his presidency.

JFK got the message. In March 1962, the president distanced himself from Sinatra by canceling a scheduled stay at the singer's Palm Springs complex, staying instead at the nearby home of Bing Crosby, a rival crooner and a Republican at that. It must have hurt: Sinatra's long-cultivated friendship with JFK was over, and the mob wasn't happy. An FBI memo later noted that "Chicago sources have advised of Giancana's disappointment in Sinatra's apparent inability to get the administration to tone down its efforts in the anti-racketeering field."

Not that Sinatra was through hanging around with tough guys. Far from it: He was so successful now, having just started the Reprise record label and flying in his own private jet, that he didn't seem to care what people thought.

He was the Chairman of the Board.

And the head of the Rat Pack. Late in 1962, he topped the bill for a week with fellow Rat Packers Dean Martin and Sammy Davis, Jr., at the grand reopening in suburban Chicago of the mob-run Villa Venice Supper Club. According to an FBI memo, the appearance by Sinatra's clan was "what can only be termed a command performance" in return for past favors from Giancana. Onstage, Dean Martin even sang parody lyrics about not getting paid for the gig.

Sinatra had the red-meat crowd roaring with a typically vicious putdown of the Hearst Broadway columnist critical of his connection to JFK: "I met many, many male finks but I never met a female fink until I met Dorothy Kilgallen. I wouldn't mind if she was a good-looking fink."

Sinatra talked the hoodlum talk, but was he walking the walk? Many in Attorney General Robert Kennedy's anti-mob Justice Department believed so. But hard evidence was elusive, as the FBI files demonstrate.

On April 24, 1963, the special agent in charge of the FBI's Los Angeles office asked Hoover to consider bugging Sinatra's home in Palm Springs. Surprisingly, Hoover promptly denied the request. "You are reminded that all misurs [microphone surveillances] must be completely justified," said the reply.

That summer, however, the FBI got a compelling new reason to keep the heat on Sinatra. At the Cal-Neva Lodge in Lake Tahoe, a casino resort in which Sinatra held a major interest, Giancana had been spotted ensconced with his girlfriend, the singer Phyllis McGuire of the McGuire Sisters. The resulting public furor-Giancana was proscribed from the casino as a known mobster-forced Sinatra to relinquish all his gambling interests in Nevada, at both the Cal-Neva and the Sands in Las Vegas.

Soon afterward, Dougald D. MacMillan, one of RFK's top mob prosecutors, arrived in Los Angeles with authority to "review all pertinent information in an effort to determine whether prosecution could be initiated against Sinatra." But his Los Angeles colleagues scoffed at his grandstanding plan to start off by grilling top stars and Sinatra friends like Dean Martin, Sammy Davis, Jr., Dinah Sh.o.r.e, and Eddie Fisher. "MacMillan is a boy on a man's errand," an FBI official scrawled on one memo. When Hoover found out about MacMillan's plan, he called it off.

Two months later, according to FBI memos, serious consideration was given to prosecuting Sinatra for denying in an interview with the Internal Revenue Service that Giancana had attended a two-week-long party he threw at the Claridge Hotel in Atlantic City. The FBI had evidence that Sinatra was lying-the testimony of a chorus girl at the party-but the matter was dropped as an "apparent, though minor, violation of the law." Sinatra would never have a closer brush with the FBI.

At least not in the legal sense: On December 8, 1963, two weeks after Kennedy's a.s.sa.s.sination, Frank Sinatra, Jr., age nineteen, was kidnapped from his hotel room in Lake Tahoe and held for ransom by three men, one of them an ex-schoolmate of the singer's daughter Nancy. Two days later, Sinatra paid nearly $240,000 to secure his son's release; the FBI arrested the three kidnappers days later.

The FBI agents who had worked closely with Sinatra throughout the ordeal felt they had made a breakthrough with the singer. One of them, Dean Elson, the bureau's special agent in charge for Nevada, had developed a "close personal relationship" with the star and suggested that he "might be able to induce Sinatra to help us," according to a memo.

But once again, Tolson and Hoover wanted nothing to do with Sinatra. "I do not agree," wrote Tolson in response to Elson's suggestion, to which Hoover added, "I share Tolson's views."

Still, the kidnapping episode demonstrated that Hoover and Sinatra shared at least one thing in common: an unforgiving att.i.tude. When a Catholic prison chaplain appealed for forgiveness on behalf of two of the kidnappers, Sinatra wrote back rejecting the suggestion as "presumptuous." He informed Hoover of his exchange with the priest in a "Dear Edgar" letter. In his "Dear Frank" reply, Hoover was in an equally unmerciful mood, quoting a judge with approval: "It is not the criminals ... that need a neuropathic hospital; it is the people who s...o...b..r over them in an effort to find excuses for the crime."

Sinatra was entering a September of his years whose bitterness belied the wistful tone of his similarly t.i.tled 1965 alb.u.m. In 1966, according to an FBI memo, he hired a Washington public relations man to "determine the ident.i.ty of the SOB" who "tagged" him as a "commie" in the 1940s. When asked why Sinatra still cared after all those years, the investigator told the authorities, "Sinatra is a very temperamental, vindictive and moody individual and has periods where he dwells on his past life."

Within a few years of Hoover's death in 1972, the FBI's interest in Sinatra trailed off, and little new information was added to the files.

But in 1981, after a swing to the Republicans, a retirement, a comeback, and a fourth marriage, Sinatra privately obtained his FBI dossier under the Freedom of Information Act. He turned it over to the Nevada Gaming Control Board as part of an effort to win back the gambling license he had lost thanks to Giancana in 1963.

Though the files offered plenty of reason to be suspicious of Sinatra, they proved no illegality. Perhaps that's why Sinatra got his license back. But it couldn't have hurt that he once again had friends in high places: One of his character references was President Ronald Reagan, whose inaugural gala the singer had hosted the previous month.

To many, it looked like the fix was in. As with so much else in Sinatra's life, the episode didn't so much clear up doubts about his character as ill.u.s.trate them.

Less ambiguous was Sinatra's statement to an interviewer in 1963: "When I sing, I believe, I'm honest."

The FBI files presented on the following pages do not refute that.

The Life of Frank Sinatra: Selected Highlights

1915.

December 12: Birth of Francis Albert Sinatra to Martin Sinatra and Natalie Catherine "Dolly" Garavante in Hoboken, N.J.

1935.

September: As a member of the Hoboken Four, wins first prize on Major Bowes and His Original Amateur Hour Major Bowes and His Original Amateur Hour.

1938.

First important nightclub gig, as a singing waiter at the Rustic Cabin in Alpine, N.J.

charged in Bergen County, N.J., with "seduction" under a false promise of marriage (and later adultery, in the same case). Charges are later dropped.

1939.

February 4: Marries Nancy Barbato.

June: Joins Harry James and His Orchestra.

First recordings with the James band, including "All or Nothing at All." James later releases Sinatra from contract so he can join the Tommy Dorsey Band.

1940.

January: Joins the Tommy Dorsey Band.

May 23: Records "I'll Never Smile Again," his first major hit, crystallizing the yearning and despair of a generation torn apart by World War II.

June 8: Birth of first child, Nancy Sandra.

1941.

Voted Outstanding Male Vocalist by Billboard Billboard and and Downbeat Downbeat.

First of nearly sixty film appearances: Las Vegas Nights Las Vegas Nights.

1942.

January: First solo recordings (with Axel Stordahl arranging) on RCA's subsidiary label Bluebird, including "Night and Day."

September: Last appearance with Dorsey band.

December 30: Appears at Paramount Theatre for the first time as an "extra added attraction" with Benny Goodman's band.

1943.

Lead singer on Your Hit Parade Your Hit Parade radio show (until 1945). radio show (until 1945).

June: First Columbia recording session, including "Close to You." Sinatra is backed by a vocal chorus because of a musicians' strike.