Thirty thousand teenage girls, unable to get seats at Manhattan’s Paramount Theatre, riot in Times Square, stopping cars and breaking shop windows. The object of their adoration? A 28-year-old big-eared beanpole named Frank Sinatra.
Upset with a newspaper columnist who wrote about his socializing with Mafia chieftains, Sinatra spots the journalist at a New York City nightclub, belts him and is arrested for assault.
With his record sales dropping and his movie career in a tailspin, Sinatra reinvents himself with an Oscar-winning performance in From Here to Eternity.
Frank Sinatra, pop singer and power broker, produces the Inaugural celebration for his friend President John F. Kennedy and escorts Jackie to the gala.
Sinatra delivers $240,000 to a deserted Los Angeles gas station for the safe return of his kidnapped son Frank Jr.
At a pre-lnaugural party for Richard Nixon, an out-of-control Sinatra lashes out at Washington Post columnist Maxine Cheshire, calling her a $2 whore and stuffing $2 into her glass.
For Sinatra’s 80th birthday, a multigenerational Who’s Who of showbiz gathers at the Shrine Auditorium in Los Angeles. They range from Tony Bennett to Ray Charles to Bruce Springsteen, Bob Dylan, Bono and Salt-N-Pepa—a trio of young women who strut, hip-hop and coo slightly revised lyrics from one of their songs: “Whatta man, whatta man, whatta man, whatta mighty good man, 01′ Blue Eyes.”
In a career encompassing some 2,000 recorded songs, almost 300 albums, 60-some films and countless TV shows and concerts, Frank Sinatra worked alongside both Bing Crosby, who preceded him, and Elvis Presley who followed him as a teen idol. He walked with Presidents and visited with Nikita Khrushchev and Queen Elizabeth. He squired a Who’s Hot of Hollywood stars, among them Ava Gardner, Marilyn Monroe, Lauren Bacall, Grace Kelly, Kim Novak and Mia Farrow.
At the birthday tribute, jokes are told about Sinatra’s penchant for fisticuffs, and a video montage includes headlines about his numerous amours, dustups and friends in low places. Sinatra smiles through it all. For every little dig, there are heartfelt salutes. “What Toscanini was to classical music,” says Bennett, “Frank Sinatra is to American popular songs.” As the stars convene for the finale, “New York, New York,” Sinatra shakes off Bennett, who offers an arm to help him to the stage, and takes the microphone. The Voice, frayed at the edges like a musical Old Glory, roars out the final words—NEWWWW…YORRROR-RRRRK!—holding the last note for an impressive 12 seconds.
Whatta man, indeed. When Frank Sinatra died of a heart attack on May 14, the accolades began again, this time from around the world. Radio and television stations played Sinatra tributes all weekend. Los Angeles’ landmark, circular Capitol Records building was draped in black. Presidents spoke—when remembering Frank, said Bill Clinton, “I think every American would have to smile and say he really did it his way”—and so, as the song goes, did puppets, paupers, pirates, poets, pawns and a King (Alan, who said, “In a hundred years, when people get together to study pop music, Sinatra will be taught—for his phrasing, his musicianship, his style”). After 82 years, it seemed almost everyone I knew—and had an opinion about—the skinny kid from Hoboken.
According to family lore, Francis Albert Sinatra entered the world fighting for his life. Born on Dec. 12, 1915, he weighed a hefty 13½ pounds but wasn’t breathing. Legend had it that he took his first gasps of air only after his grandmother held him under a cold faucet. During the difficult delivery, the doctor tore the boy’s left ear-lobe and cheek. Sinatra would carry the scars for the rest of his life.
An only child, Frank grew up in the Little Italy section of Hoboken, N.J., a former resort town just across the Hudson River from Manhattan. “My mother was very modern in a sense and fairly ambitious,” Sinatra said. “She went to nursing school and became a midwife. And she was a troubleshooter.” Natalie Catherine “Dolly” Sinatra was, in fact, a fixer: Frank’s father, Martin, a soft-spoken former boxer, owed his later career as a fireman to her connections. A woman of prodigious political skills, she became a prominent Democratic party district leader who could go to city hall and extract favors for family, friends and neighbors. In the Prohibition era she opened a tavern. Extending her work beyond midwifery, she also performed abortions.
At 15, Sinatra was expelled from A.J. Demarest High School for what he later characterized as “general rowdiness.” He worked on the waterfront and at a local paper, but his heart was in having a singing career like his idol Bing Crosby. Dolly bought him a $65 sound system that gave him an edge over the competition. Later, when she heard that a local group, the Three Flashes, was to appear on a popular radio show, Major Bowes and His Original Amateur Hour, Dolly leaned on the boys to bring her son onboard. Appearing on Bowes as the Hoboken Four, they were such a hit that Bowes booked them for a national caravan tour.
Performing one-nighters from Chicago to Seattle, Sinatra learned his craft. He also learned about jealousy: When women in the audience showed a distinct preference for Frank, other members of the Hoboken Four took to beating him up after the shows. He left the tour early.
His next break came while he was working as a singing waiter and emcee at the Rustic Cabin near Alpine, N.J. The pay wasn’t much—$15 a week—but Sinatra knew the club’s shows were broadcast on radio and recognized the value of publicity. One evening trumpeter Harry James, who was starting his own band, came by to hear the singing waiter from Hoboken—and signed him for $75 per week. Neither Frank nor his new wife, former childhood sweetheart Nancy Barbato, could believe their luck.
Still, Sinatra was thinking bigger. Soon he heard that Tommy Dorsey, one of the most popular bandleaders of the day, was looking for a new singer. James, ever the gentleman, tore up Sinatra’s contract and let him go. At his first performance with Dorsey, in Indianapolis in February 1940, Sinatra “broke it up completely,” Jack Egan, a Dorsey friend, recalled. “When Frank started slurring down on those notes…the kids started screaming.”
And so it began. By the end of that year, Sinatra had his first No. 1 hit, “I’ll Never Smile Again,” and in 1941 he was named top male vocalist by Billboard. In later years, Sinatra always said that he learned to breathe properly and hold notes for exceptionally long stretches by watching how Dorsey played the trombone. “Instead of singing only two bars or four bars of music at a time—like most of the other guys around—I was able to sing six bars, and in some songs eight bars, without taking a visible or audible breath.” That flowing quality of his singing became a Sinatra signature.
After an acrimonious split from Dorsey—who tried to hold Sinatra to an extortionate 10-year contract—Sinatra went solo and was booked as an “extra added attraction” with King of Swing Benny Goodman for the New Year’s show at New York City’s Paramount Theatre. The moment Sinatra stepped onstage, he later recalled, “the sound that greeted me was absolutely deafening, a tremendous roar…. I was scared stiff….Benny froze too. He turned around, looked at the audience and said, ‘What the hell is that?’ I burst out laughing.” Sinatra’s press agent George Evans later admitted he had paid a gaggle of teenage girls to scream Frankie’s name and faint on cue. From that small spark did a wildfire ensue: Soon thousands of bobby-soxers were swooning for real, starting fan clubs—including Slaves of Sinatra and the Hotra Sinatra Club—and buying records by the truckload. The singer, who was unfit for military service because of a punctured eardrum incurred at birth, thought wartime emotions played a role in his popularity. “It was the war years, and there was a great loneliness. I was the boy in every corner drugstore, the boy who’d gone off to war.”
The spotlight Sinatra had sought so hungrily was his. It brought attention from the press, which he came to despise. Of Hollywood reporters in particular he once said, “All day long they lie in the sun, and when the sun goes down, they lie some more.” Still, much of the trouble was of his own making. In 1947 he traveled to Havana and fraternized with gang lord Lucky Luciano. A journalist, Lee Mortimer, berated the singer in his column for meeting with mobsters. When Sinatra later spotted Mortimer in a bar, he punched him. Sinatra also drew attention to himself with a string of affairs, including a protracted and very public courtship of Ava Gardner. The Sinatras, who by 1950 had three children—Nancy, 9, Frank Jr., 6, and Tina, nearly 2—separated that year and would soon divorce.
By then Sinatra’s career was in trouble. He had displayed his versatility in several movies and earned a special Oscar for The House I Live In, a short film about tolerance. But more recent movies, like The Kissing Bandit, had flopped, his record sales were falling, and one night at the Copacabana his voice gave out completely. (Doctors later determined that a vocal cord had hemorrhaged.) His personal life was also a mess: In 1950, on the outs with Gardner, who would become his second wife, he phoned her from a hotel room, told her, “I can’t stand it any longer, I’m going to kill myself—now!” and fired two shots into a mattress, leaving her to think he had taken his life. (Alerted by Gardner, friends found the inebriated singer and cleared up any evidence of trouble before police arrived.)
Written off as yesterday’s teen fad, Sinatra battled tenaciously to come back. A gritty movie role as a tough, good-hearted soldier from Brooklyn in From Here to Eternity brought him a 1953 Oscar and the respect he craved. Almost simultaneously, his new bosses at Capitol Records, where he had signed a one-year contract, paired him with arranger Nelson Riddle. With Riddle’s encouragement, Sinatra, a longtime jazz fan, began to swing a little, toying with phrasing and lyrics.
“I don’t know what other singers feel when they articulate lyrics,” he once told Playboy magazine, by way of explaining his ability to connect with listeners. “But being an 18-carat manic-depressive and having lived a life of violent emotional contradiction, I have an over-acute capacity for sadness as well as elation.” By 1954 he was on the charts with “Young at Heart”—and-began to strut again.
As always, he made news—good and bad. When pal Sammy Davis Jr. lost an eye in an automobile accident, Sinatra rushed to the hospital to offer comfort. He gave lavishly to charity and performed at benefits. But there were other headlines too. In a 1954 scandal that became known as the “wrong door raid,” persons unknown kicked down the front door of a Hollywood apartment. Evidence mounted that Sinatra and his friend Joe DiMaggio were behind the raid and had been looking for DiMaggio’s estranged wife, Marilyn Monroe. During hearings a potential witness told the police he had been beaten up by men he believed were sent by Sinatra. No indictments were ever issued.
Predictably, Sinatra was unhappy with his portrayal in the press. A six-part series by syndicated columnist Dorothy Kilgallen so riled him that he sent her a tombstone engraved with her name. For years afterward, he would insult her during his shows, calling her the chinless wonder. (Later, hearing of her death, Sinatra remarked, “Guess I got to change my whole act.”) Public vilification of perceived enemies would become a trademark.
There was no controversy, however, about the quality of his singing. In 1958, Come Fly with Me topped the charts; Frank Sinatra Sings for Only the Lonely was a mopers’ masterpiece; and Come Dance with Mel earned two 1959 Grammys, for album of the year and best vocal performance, male. Sinatra also commanded the world” stage, emceeing a film premiere attended by Queen Elizabeth and hosting a luncheon honoring Soviet Premier Nikita Khrushchev.
Sinatra had recently met John F. Kennedy, the young Massachusetts senator whose sister was married to actor Peter Lawford, a Sinatra pal. A lifelong Democrat, Sinatra was excited to be enlisted for the Kennedy campaign. He rerecorded his hit “High Hopes” with special, pro-JFK lyrics and in late 1959 entertained Kennedy at his Palm Springs compound. Later, Sinatra put a brass plaque that read “John F. Kennedy Slept Here” on a guest-bedroom door.
When Kennedy won the election, Sinatra was exultant. Asked to oversee the Inaugural, he commandeered performers—including Nat King Cole and Jimmy Durante—and oversaw every detail. Jacqueline Kennedy arrived at the gala on Frank’s arm. Sinatra was in his glory—and then the roof fell in.
After the election, Robert Kennedy, the newly appointed Attorney General, studied FBI files on Sinatra and, citing the singer’s alleged Mob affiliations, suggested that his brother cool the relationship. Sinatra, in anticipation of a long-scheduled presidential visit, had added on to his Palm Springs house and even built a helipad. At the last minute, President Kennedy canceled the Sinatra visit and stayed nearby with Bing Crosby instead. Humiliated and angry, Sinatra reportedly smashed the helipad with a sledgehammer.
Professionally, Sinatra was going gangbusters. One report estimated he was earning $20 million a year from records, movies and ownership or interest in film companies, radio stations, a record company and real estate, including a casino, the Cal-Neva Lodge. His associations once again made headlines when the Nevada Gaming Commission accused him of knowingly playing host to Sam Giancana, a notorious mobster, at Cal-Neva. When Commissioner Edward Olsen launched an investigation, Sinatra, he said, phoned him and “called me every name in the book. I had never heard some of the things he called me.” Just before a formal hearing was to take place, Sinatra sold his interest in Cal-Neva.
The assassination of President Kennedy that November devastated Sinatra. “For three days…my father grieved alone, locked away in his bedroom,” his daughter Nancy later wrote. But there was little time to mourn. Sixteen days after Kennedy’s death, thugs broke into a Lake Tahoe lodge and kidnapped Frank Sinatra Jr., then 19, who had embarked on a singing career. After two tense days, Sinatra paid a $240,000 ransom, Frank Jr. was released, and the three kidnappers were quickly apprehended. At the trial, their lawyer claimed that the entire episode had been set up by Frank Jr. to get publicity. Scoffed Sinatra Sr.: “This family needs publicity like it needs peritonitis.” The jury didn’t buy the argument either. Two of the kidnappers were sentenced to life in prison, the third to 75 years.
Sinatra turned 50 in 1965 and—after a brief engagement to Juliet Prowse and relationships with actress Jill St. John and others—announced that he didn’t want to marry anyone in show business. Then, promptly, he contradicted himself in spectacular style: Following a whirlwind public courtship, he married actress Mia Farrow, 21, in 1966. Sixteen months later they separated. Farrow confessed that, despite their love, she could never fit in with his life of gambling, bar brawls and carousing.
His career only improved. “Strangers in the Night,” with its throwaway “doobie-doobie do,” gave him his first No. 1 single in more than a decade. “That’s Life” again pumped him into the Top 10. Finally, in 1967, he scored a multimillion-selling single, “Somethin’ Stupid,” by teaming up with daughter Nancy. It was cotton candy on vinyl, but it clicked.
The dark side of Frank, as always, continued to make news. A dinner party at the Polo Lounge to celebrate Dean Martin’s birthday erupted in an argument between Sinatra and a businessman at a nearby booth. The businessman ended up at a hospital with a skull fracture. No one was ever charged.
In Las Vegas, at the Sands casino—home turf of the Rat Pack, Sinatra’s hard-partying band of showbiz pals—Sinatra allegedly went on a rampage when the house cut off his credit line after he ran up some $50,000 in gambling debts. He confronted a Sands executive, Carl Cohen, and tried to hurl a table at him. Cohen responded by punching Sinatra in the mouth. (A similar incident, again sparked by gambling debts, occurred at Caesars Palace three years later. That one ended only after Sanford Waterman, the casino’s manager, drew a pistol on Sinatra.) Sinatra wrapped up 1968 by recording his almost belligerent manifesto, “My Way.”
In March 1971, Sinatra did the utterly unexpected: He announced his retirement. “It has been a fruitful, busy, uptight, loose, sometimes boisterous, occasionally sad but always exciting three decades,” he said. Now, he wanted time “for reflection, reading, self-examination.” He denied that he was ill or that he feared becoming stale: “I just quit, that’s all. I don’t want to put any more makeup on. I don’t want to perform anymore. I’m not going to stop living. Maybe I’m going to start living.” For his final number at his farewell concert in Los Angeles, he sang an old saloon song, “Angel Eyes.” After the last line—”Excuse me while I disappear”—he walked slowly offstage.
Sinatra stayed retired—for all of 16 months. Feeling spurned by the Democrats, he supported Richard Nixon in 1972 and became good buddies with Spiro Agnew. In 1973 he performed at the White House and, warmed by the reception, began thinking seriously about a return to the public stage.
The comeback came in the form of a TV special and an album, both titled Ol’ Blue Eyes Is Back. The inevitable headlines followed close behind. On a tour of Australia, members of his entourage got physical when a reporter approached to ask for an interview. Sinatra didn’t help the situation when he publicly called local reporters “parasites, hookers and pimps.” Australian unions showed their outrage by refusing to move stage props, deliver room service or even fuel Sinatra’s plane until he apologized. He did, grudgingly.
The late ’70s and ’80s saw the emergence of Sinatra as the tuxedoed gray eminence of pop. He settled, at last, into a marriage that worked: Fourth wife Barbara Marx was a former showgirl and an ex-wife of Zeppo Marx. She understood his world and was willing, as two previous Mrs. Sinatras had not been, to play the role of supportive wife.
Professionally he showed no hint of retiring. He organized Ronald Reagan’s Inaugural galas in 1981 and 1985 and served as unofficial entertainment coordinator at White House functions. He gathered awards, including the Kennedy Center Honor for Lifetime Achievement in 1983 and an honorary doctorate from the Stevens Institute of Technology in Hoboken, where as a youth he had hoped to study bridge building. “I wanted to be an engineer,” Sinatra recalled. “It was my great desire until I got mixed up in vocalizing.” He hit the road with Sammy and Dean in 1988 (an ailing Martin would soon be replaced by Liza Minnelli) and, for good measure, released the best-selling album of his entire career, Duets, in 1993. More than 50 years after he began singing professionally Frank Sinatra gave his last full concert, in Japan, on Dec. 20, 1994.
By the time he turned 80, Sinatra had well earned the party at the Shrine.
The last performer that night was the first to break form, to not do a Sinatra song or a number customized for the honoree. But Bob Dylan, in singing his 1964 ballad “Restless Farewell,” chose wisely. The song concluded:
Oh a false clock tries to tick out my time
To disgrace, distract, and bother me.
And the dirt of gossip blows into my face,
And the dust of rumors covers me.
But if the arrow is straight and the point is slick,
It can pierce through dust no matter how thick.
So I’ll make my stand
And remain as I am
And bid farewell and not give a damn.
Sinatra, who most likely did not have a Dylan album in his collection, beamed.