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New York Daily News
PUBLISHED: | UPDATED:

(Originally published by the Daily News on May 15, 1998. This story was written by David Hinckley.)

Frank Sinatra sang with a fierce intensity, like a man in pursuit of that one elusive moment when the song would be precisely as he wanted it to be.

He lived the same way, and when he died yesterday, he probably would have said that he never reached that moment that in the end it remained one step and one note beyond his grasp.

That’s the nature of perfectionism, which was the nature of Sinatra. But he went so far and came so close, at least in song, that for more than 50 years he lifted millions of music lovers a little closer to their own perfect moments.

As smoothly as he sang, his path apart from music was just as rough, and his missteps were well chronicled. Sinatra was a celebrity in the full sense of the word, a public figure in a century eager to strip away all privacy.

SINGER AND SWASHBUCKLER

When Sinatra left Tommy Dorsey’s band for a solo career in 1942, it was high drama unresolved until the screams of 5,000 teenage girls filled the Paramount. When he left his hometown sweetheart, Nancy, hometown girls all over America felt they, too, had been betrayed, and it was with mixed emotions that America watched Sinatra’s often desperate pursuit of the hot-blooded Ava Gardner while his singing career went cold in the early ’50s.

When he resurrected his career with an Oscar-winning performance as the scrappy Private Maggio in the 1953 movie “From Here to Eternity,” that, too, was folded into the drama: Cocky kid wins by not getting humble. It was only necessary to look at the tilt of his hat on his classic ’50s Capitol albums to understand that he played by his own rules.

In that decade of storied nightlife, Sinatra became a cornerstone, a godfather presiding over a circle of friends who defined the good life as they went along and let the rest of the world watch.

So watch we did: the laughter, the drinks, the parties, the dames, the fights and the mornings after. If it wasn’t all glamor, at the very least it looked larger than life.

Thus did Sinatra, who in his prime looked to weigh about 75 pounds including the shot glass, come to define the modern meaning of “swashbuckler.” While he had a private side the extensive donations to charity, the painting, the spells of solitary reflection his public posture was that when he walked, everyone else got out of the way.

Walk alongside him and you were his friend, maybe clan, maybe even family. Get in his way and you were his enemy.

He was equally quick to take on rock ‘n’ rollers, ’60s protesters and a U.S. Senate committee he felt had tarred his name with mob allegations. When columnist Maxine Cheshire displeased him, he stuffed $ 2 in her drink and called her a “two-dollar hooker.”

Sinatra talked a lot about punch-outs, a logical adult legacy for a kid who’d grown up with a skinny chest and a big mouth. But the streets of 1920s Hoboken never washed away in his bathwater, and as he grew in wealth and musical stature, actions once dismissed as the outbursts of a young hothead came to be seen as the arrogance of a bully. When he married the much younger Mia Farrow in 1966, he was portrayed as a rich patriarch with a new toy.

But a brief “retirement” in the early ’70s seemed to wipe much of the slate clean, and after his return in 1973, he was primarily again seen as Frank Sinatra, Singer.

He married Barbara Marx, ex-wife of his good friend Zeppo Marx, in 1976, and he stayed with her for the rest of the ride. He and his pals still occasionally got their testosterone up, but even the 1986 biography by Kitty Kelley, which focused on the fights, feuds and other least flattering areas of his life, mostly ended up as a reminder: It was his singing that would endure.

And sing he did, nearly to the end. Some nights were diamonds, some were stone. But even on a bad night, there would invariably be a moment, a note and a familiar chill.

If Frank Sinatra was not the greatest popular singer ever, no discussion of the short list can be conducted without him. Bing Crosby? Billie Holiday? Sinatra learned from them, praised them, and if there’s a show tonight in the afterlife, he joins them at the top of the bill.

Listing Sinatra’s achievements is like listing New York Yankees pennants. Musically, he created exquisite catalogues on the Columbia, Capitol and Reprise labels. His concerts were cultural events for half a century even as, in the words of his friend Sammy Cahn, his voice evolved from violin to viola to cello. He influenced hundreds of singers, black and white, and he brilliantly carried the torch for Golden Age popular standards even as the music business tried to cast them aside.

His reward from this success was living the life he chose. If he wanted to go out with friends and have a long, loud, boisterous evening at a restaurant picking the place, time, food, wine, friends, topics of discussion and moment of termination himself he did.

Beyond his four marriages, he built a family of male friends, the most famous of whom made up the Rat Pack, a hard-partying bunch that included Dean Martin, Sammy Davis Jr., Peter Lawford, Joey Bishop, Jimmy Van Heusen and Cahn.

When time dissolved the Rat Pack, Sinatra took to company like the late Jilly Rizzo, a Manhattan restaurateur and sometime bodyguard.

“It was an extraordinary thing,” said Jonathan Schwartz, the New York radio personality who was one of Sinatra’s most ardent admirers and most accomplished chroniclers. “Here was a man who created some of the most sublime, exquisite musical art in history and yet his closest confidante, the man in whose company he felt most comfortable, was a man who was crude, barely literate.”

Sinatra acknowledged something of that paradox himself in a 1961 interview where he said he led a lonely life because he was his own product. He had to hit the notes, he had to make the records. Generous as he was in praising arrangers, musicians and writers, he knew that in the end, it was what he did that made or broke the deal.

“After going it alone all day,” he said, “I have to go it alone afterward.”

Sinatra lore is also sprinkled with stories like the one recounted by writer Pete Hamill, former editor of the Daily News, whom Sinatra one evening summoned for a cab ride to nowhere. Here’s possibly the greatest singer alive, Hamill wrote later, and somewhere inside there’s still a guy moving through the Manhattan night asking the questions that don’t have answers, just trying to figure things out.

Hamill did not have to spell out the punch line, which is that if Sinatra had not retained that restlessness, he could not have sung the definitive version of “Guess I’ll Hang My Tears Out to Dry,” or a hundred other songs about being alone with yourself in the wee, small hours.

Frank Sinatra is surrounded by a crowd of admiring women as he arrives for singing and movie engagements in Pasadena, Calif., August 11, 1943.
Frank Sinatra is surrounded by a crowd of admiring women as he arrives for singing and movie engagements in Pasadena, Calif., August 11, 1943.

His genius was that he was equally adept at conveying the joy of love that clicked, and the gamut of aches and thrills in between. It was this versatility that led Schwartz to say that to many of his fans, Sinatra’s death marks the symbolic end of the 20th century.

It’s a bold assertion, but a sturdy one. Other deaths have sealed the ends of eras, from Franklin D. Roosevelt to Mickey Mantle, but few other artists have been a sheer presence on the level of Sinatra for anywhere near as long.

While the best instincts of the human race spent the 20th century in mortal combat with the worst, creating a thunderous drama of triumph, tragedy, beauty, horror and raw emotion, Sinatra was a skinny kid who reminded everyone what was at stake in this battle: love, and the right to live free enough so love was possible.

SLACKSY’ FROM HOBOKEN

Francis Albert Sinatra was born Dec. 12, 1915, in Hoboken, N.J. He weighed 13 1/2 pounds and his breech birth was so difficult he didn’t breathe until his grandmother, Rosa Garavanti, held him under a cold-water tap. He suffered a punctured eardrum during the delivery, plus facial scars so severe his baptism was delayed four months.

His parents were Natalie Garavanti, known to all as Dolly, and Martin Anthony Sinatra. He was a laborer, she a dominant force in everyone’s life. She was also fiercely protective of her only child, who grew up in the pampered world of his family circle.

By his teens, when he was making outside friends, they knew him as a scrappy kid who shot off his mouth and hated ethnic insults. He also wasn’t too fond of school work, being more interested in style and music. He was nicknamed “Slacksy” because Dolly kept him so well-dressed, and for his 15th birthday his uncle Domenico gave him a ukelele.

So it was more with music than classes on his mind that Sinatra entered Demarest High School on Jan. 28, 1931. He immediately began organizing bands for school dances, insuring his own place as a vocalist until he dropped out or, he sometimes later said, was expelled 47 days later.

Since he wasn’t yet 16, Dolly coaxed him into enrolling at Drake Business School. But when he hit 16, over her dire warnings, he went off to sell himself as a singer.

He sang at local dances and social clubs, sometimes at New York’s Village Inn for free, while supporting himself with odd jobs. One night around 1932, he took his girlfriend Nancy Barbato to see Bing Crosby sing at the Loews Journal Square Theater and told her afterward he could do that, too.

He won an amateur-night contest at the State Theatre in Jersey City. He talked his way into the Hoboken Four, and they won the Major Bowes Amateur Hour on Sept. 8, 1935. Dolly got him a booking at the Union Club in Hoboken.

Then, in August 1937, he got the gig that clicked: singing with the Harold Arden Band at the Rustic Cabin in Alpine, N.J., where he doubled as headwaiter and maitre d’. Most critical, the Rustic Cabin had a network radio hookup.

‘NIGHT AND DAY’ AND OTHER FIRSTS

He married Barbato on Feb. 4, 1939. In June, bandleader Harry James heard him sing on WNEW’s “Dance Band Parade,” came out to the Rustic Cabin and hired him for $ 75 a week triple his Cabin salary. His first date with James was June 30, 1939, at Baltimore’s Hippodrome.

Two weeks later, on July 13, he cut his first record with James, “Melancholy Mood” and “From the Bottom of My Heart.” He wasn’t credited on the label, and the record didn’t sell much, but word spread on this kid vocalist and in December he was lured away by Tommy Dorsey.

His first Dorsey date was Jan. 26, 1940, in Rockford, Ill., and his first recording was “The Sky Fell Down,” on Feb. 1. His first child, Nancy, was born June 7, 1940, and on July 20, “I’ll Never Smile Again” went to No. 1. In August he made his first film, “Las Vegas Nights,” and by May 1941, Billboard’s annual survey had Sinatra displacing Crosby as the country’s favorite male vocalist.

He cut his first four solo sides on Jan. 19, 1942, including “Night and Day.” In July, he did his last studio sessions with Dorsey and on Sept. 19, after just two years, he left the band. There was strain on both sides, though Sinatra never failed to acknowledge Dorsey’s artistic impact particularly on his phrasing.

Sinatra’s first solo concert was Dec. 30, 1942, as an “Extra Added Attraction” on the Benny Goodman New Year’s show at the Paramount in New York. When he took the stage, a deafening roar signaled the start of bobbysox mania though there’s some evidence that his press agent, George Evans, masterfully stoked legitimate popularity into a juggernaut.

Whatever the reason, in February he started a two-year run on radio’s top showcase, “Your Hit Parade,” and on June 7, 1943, he did his first recordings for Columbia.

He finished his first Hollywood movie, “Higher and Higher,” in September a month before he was classified 1-A. Now many entertainers who were drafted, even at the height of the war, got noncombat assignments as entertainers-in-the-Army. Still, there was a major sigh of relief from mortified fans when he was reclassified 4-F in December because of his punctured eardrum.

In January 1944, he defended jazz against charges it contributed to juvenile delinquency. On Jan. 10, his son, Frank Jr., was born. He had tea with FDR at the White House in September and on Oct. 12 he began a return run at the Paramount that marked the peak of bobbysox fever, with 25,000 fans clogging Times Square outside the theater.

He put this popularity to use a year later by doing a short film built around “The House I Live In,” a call for racial harmony. He won a special Oscar for it. Late 1945 also marked the release of his first major film, “Anchors Aweigh,” with Gene Kelly. By 1946 Modern Screen had voted him the country’s top movie star, he was profiled in The New Yorker and he mentioned that he had already made his first million.

THE WORLD ON A STRING

The other side of success soon followed, with the first allegations in early

1947 that he associated with mobsters a charge that followed and infuriated him the rest of his life. He never denied that it could be true, he just said that he never cared what his pals did for a living.

Still, despite more movie success and the birth of a third child, Christina (“Tina”), on June 20, 1948, the Sinatra wave seemed to have crested by the late ’40s. Then, on Dec. 8, 1949, at the premiere of “Gentlemen Prefer Blondes,” he met Ava Gardner.

Frank Sinatra (right) and Marlon Brando in a scene from the 1955 film, “Guys and Dolls.”

She became the passion of his life, and on Feb. 14, 1950, Sinatra and Nancy separated amid many headlines and just as many rumors.

He tried to sing his way through it. He made his television debut in May 1950 on the Bob Hope show, impressing CBS enough that the network offered him $ 250,000 a year to host a show of his own. It started Oct. 7.

Like several subsequent attempts, however, it was not particularly successful. The small screen never quite captured the stage magic.

On Oct. 30, 1951, Frank and Nancy divorced, and on Nov. 7 he married Gardner a stormy marriage that would last less than two years while his image almost drowned. His record sales fell, his swagger was cast in a darker light.

In October 1952, the police were called in to break up a fight with Ava, and she moved out. They reconciled, but it didn’t last, because as much as he wanted her, he also didn’t want her telling him he couldn’t drink until 4 a.m. with his buddies, which he was doing a lot.

On Oct. 29, 1953, after two long and rocky years, MGM announced Gardner and Sinatra were separating and while they weren’t formally divorced until July 1957, he was found three weeks later in an elevator with his wrists slashed.

He was hospitalized and released with a statement that he was suffering from exhaustion and emotional strain, and that the slashing was an accident.

Meanwhile, Sinatra had also left Columbia Records, which he saw as a dead end after producer Mitch Miller’s abortive attempts to revive his popularity with duets and novelty tunes like “Mama Will Bark.” He did his final Columbia session on Sept. 17, 1952.

The musical lull, mercifully, was short. He signed with Capitol and soon hooked up with Nelson Riddle, an arranger who appreciated the same classic songs and had an instinctive feeling for how Sinatra sang both ballads and swing tunes. By midsummer, Sinatra had started a new run of top-20 hits with “I’ve Got the World on a String,” and as the decade wore on, he and Riddle created some of the definitive albums of the 20th century, including “Songs for Swingin’ Lovers” (1956), “Come Fly With Me,” “Only the Lonely” (1958) and “Come Dance With Me” (1959).

His most spectacular revival, however, took place on the screen, with the August 1953 release of “From Here to Eternity,” which won him his second Oscar and propelled him into “Young at Heart,” “Guys and Dolls” and “The Man With the Golden Arm” in 1955, then “High Society” in 1956 and “Pal Joey” in 1957.

This was also the Rat Pack’s peak, and as Sinatra began to recover from Gardner, he became more outspoken. In 1957, he denounced rock ‘n’ roll as “the most brutal, ugly, degenerate, vicious form of expression it has been my displeasure to hear. … It manages to be the martial music of every sideburned delinquent on the face of the Earth.”

This outburst foreshadowed a broader evolution in his social and political views. Over the next quarter-century, the FDR/JFK Democrat gradually became a Reagan Republican a shift he said reflected a change in the political spectrum, not his ideals.

WAR MOVIES AND MIA

Frank Sinatra smiles during a concert on his 75th birthday at the Meadowlands Area in East Rutherford, N.J., Dec. 13, 1990.
Frank Sinatra smiles during a concert on his 75th birthday at the Meadowlands Area in East Rutherford, N.J., Dec. 13, 1990.

There were milestones in his evolution, however. In 1960, he hired the blacklisted Albert Maltz, an old friend, as screenwriter for the movie “The Execution of Private Slovik.” Sinatra had spoken out strongly against blacklisting in the ’50s. But when political pressure intensified, Sinatra fired Maltz, saying, “I will accept the majority opinion.”

Meanwhile, he opened the decade by hosting a TV show with newly discharged Army veteran Elvis Presley, and later that year he started Reprise Records, recording his first Reprise album, “Ring-a-Ding-Ding,” in December.

In early 1962, he had a six-week engagement to Juliet Prowse and in early 1963 recorded his classic album of jazz songs with Count Basie. Nothing stayed tranquil for long, however: On Dec. 8, 1963, Frank Jr. was kidnaped. Sinatra paid a $ 240,000 ransom, Frank Jr. was rescued, the kidnapers were caught and the money recovered.

In the movies, meanwhile, he was shifting from musicals to war movies and cop flicks like “None But the Brave” (1965), “The Detective” and “Lady in Cement” (1968).

Musically, he spent the mid-’60s trying to change with the times, and didn’t do badly with pop hits like “Strangers in the Night,” “That’s Life” (1966) and “Somethin’ Stupid” (1967). “My Way,” which barely cracked the top 30 in 1969, was soon adopted by many fans as his anthem.

In the middle of this, on July 19, 1966, he married Mia Farrow. He was 50, she was 21. Everyone said it wouldn’t last, and it didn’t. The divorce was finalized barely two years later, in August 1968.

After Martin Sinatra died on Jan. 29, 1969, Frank told friends he was shaken, and on March 21, 1971, he announced he was retiring. A farewell gala on June 13 ended with Sinatra onstage in near-total darkness. He lit a cigaret, the smoke enveloping his silhouette, and he sang “Angel Eyes,” whose last line is “Excuse me while I disappear.”

OL’ BLUE EYES IS BACK

But not for long. He returned on Nov. 18, 1973, with an acclaimed TV show called “Ol’ Blue Eyes Is Back.”

By early 1974, he was back in Vegas and he became a grandfather. A round of world tours followed, and in July 1976, he married Barbara Marx.

On Jan. 6, 1977, a plane carrying Dolly Sinatra from Palm Springs to see Frank perform in Las Vegas disappeared. Two days later, the wreckage was found. No survivors.

Sinatra continued his live shows, but it was two years before he released another record: “Trilogy,” a swelling three-disc set that struck some as an uncharacteristically clumsy attempt to immortalize himself.

Still, the milestones and accolades were routine by now. He played the Pyramids in Egypt. In Rio, he drew 175,000. The Songwriters Hall of Fame honored him and he was grand marshal of New York’s Columbus Day parade. He organized the Reagan Inaugural gala in 1981, as he had the Kennedy gala 20 years before.

Frank Sinatra, right, and Dean Martin, arrive at London's Heathrow Airport in this Aug. 4, 1961 file photo.
Frank Sinatra, right, and Dean Martin, arrive at London’s Heathrow Airport in this Aug. 4, 1961 file photo.

He had one solo album left, the lush 1984 “L.A. Is My Lady” with Quincy Jones, and almost 10 years later he finished his studio career with the two “Duets” albums, where he cut his tracks and other noted performers separately added their parts.

While some critics compared these unfavorably to his own earlier recordings, both “Duets” albums sold well and were generally seen as a dignified final punctuation artists who had loved Sinatra’s work thanking him while brushing against the master.

He closed his film career even more quietly, last starring in “The First Deadly Sin” (1980) and doing a brief cameo as himself in 1984’s “Cannonball Run II.”

The concerts, fittingly, were the last to go. His 1980s and ’90s shows were uneven. Stage monitors scrolled the lyrics to his best-known songs, his voice was not always crystal-clear and his range had narrowed.

But to the end the fans came, and to the end they did not leave disappointed. Sinatra’s last public note – as part of a chorus finishing “New York, New York” at his 80th birthday gala in Los Angeles in 1995 – deserved the standing ovation it inevitably received.

WINDING DOWN

Offstage, meanwhile, the man who had lived so long in the fast lane was taking his foot off the accelerator. Although he tolerated a TV miniseries on his life and endorsed a biography by daughter Nancy, he spent more time in private, at home, toupee off, listening to music, sometimes painting.

By the 1980s and ’90s, too, his friends were checking out: Sammy Davis Jr., Sammy Cahn, Jilly Rizzo, Dean Martin. Some of those deaths reduced his social circle. Others deepened the shadow of mortality – the shadow that makes most people wonder if they want to be the last to go.

Whether Sinatra felt that way it’s hard to know. But he loved being alive so much that he had a standing joke on the subject, one he told in concert for years.

“May you live to be a hundred,” he would say, lifting his omnipresent glass full of amber liquid. “And mat the last voice you hear be mine.”

Perfect?

Close enough.