frank sinatra

When the news came, on the late evening of May 14, 1998, that Frank Sinatra had died at age eighty-two of a massive heart attack, it did not come as a shock—though it immediately hit as an immense loss. Sinatra had been known to be in seriously failing health for over two years. What’s more, he was a man who had lived a long life and had lived it hard: He drank too much, smoked too long, and raged and wept far too many times—as if he could afford all these hazards without risking his grasp on his talent. Apparently, he could. He became a huge pop star in the early 1940s—he was, in fact, American music’s first titanic sex sensation—and despite setbacks and his own precarious temperament, he kept both his passion and his prodigy intact for several decades. As the years went along, he became an intense, deeply affecting actor, playing complex, tortured characters. He became a friend to presidents as well as a companion to gangsters. He became an idol to the rich and common man alike. And at times he behaved like a vile-tempered thug—though one with a reputation for matchless generosity.

As a result, for nearly sixty years Frank Sinatra proved to be one of pop music’s most abiding paragons—and also one of its most unsettling icons. At the peak of his craft, Sinatra raised the art of romantic singing to a new height, treating each song as if it were the inevitable expression of a personal experience—as if there were no separating the singer from the emotion or meaning of the songs he sang, and therefore, no separating the listener from the experience of a singular and compelling pop voice. But for all the grace of his talent, there was also a substantial darkness about Sinatra: a desperate hunger for the validation that comes from love and power and a ruinous anger for anything that challenges or thwarts that validation. In many ways, that fierce need for love or vindication proved the guiding force behind the best moments of Sinatra’s career. In the end, his singing amounts to the life testament of a man who learned to cling to one truth above all others: namely, that one could never win love so surely that one could stop imagining the pain of its loss.

Looking at his story, now that it has finished, it makes a certain rueful sense that it was Sinatra’s blazing, difficult heart that would finally take his life.

HE WAS BORN Francis Albert Sinatra in Hoboken, New Jersey, on December 12, 1915, to Marty and Dolly Sinatra, a young Italian immigrant couple. Sinatra’s birth was difficult—nearly fatal for him and his mother. The delivering doctor had to use forceps to wrest the infant from Dolly’s body. Sinatra carried lifelong scars around his face, and Dolly could bear no other children.

Sinatra’s father had been a boxer, a boilermaker, and a consort to liquor bootleggers, and later, he would run a bar with his wife. But Marty Sinatra was also a quiet man, said to be shy and lonely, and he is almost invisible in Sinatra’s legend. Rather, it was Frank’s enterprising mother, Dolly, who dominated the family’s temperament and who indelibly shaped much of her son’s own character and needs. Dolly was a smart and strong woman—sly if it served her purposes; ruthless if she saw fit. In Sinatra’s youth, she worked as a sometime abortionist and Hoboken Democratic ward boss and helped her husband in their saloon: Marty O’Brien’s. She adapted herself well to the company that she moved in: She could be eloquent at political gatherings and rough-mouthed and profane in the company of family, friends, and enemies—and these same traits also distinguished Sinatra throughout his life. In addition, Dolly doted on Frank—she provided him with nice clothes, a car, and cash to entertain his friends. But as John Lahr points out in his superb analytical biography Sinatra: The Artist and the Man, Dolly also withheld her love and punished her son when he did not match her expectations. This mix of generous reward and stern penalty formed the way that Sinatra learned how to find love, and how to give it as well, and it became a pattern that he repeated many times in private and public ways.

Frank’s parents wanted him to pursue a higher education. In particular, Dolly wanted her son to gain work as a journalist. (When Sinatra’s godfather, Frank Garrick, wouldn’t support Frank’s attempt to land a sportswriter job at a local newspaper, Dolly never forgave Garrick and refused to speak to him again. She later boasted that she was the person who taught Frank never to forget a slight.) Sinatra, though, had ambitions of his own. He longed to leave the delimiting prospects of Hoboken and to cross over the Hudson River to the dream life that might be found in New York. And he thought he had discovered the means to that goal in his parents’ bar, during the moments in his late childhood when he sang along with the pop songs that played on the music roll of the player piano. Sinatra wanted to be a singer—like his youthful idol, Bing Crosby—and he developed a fervent belief in his voice. At first Dolly resisted, and even disparaged, Frank’s hope. But when her son’s determination outmatched her own, she used her considerable skills to help him. When Sinatra was almost twenty, Dolly persuaded a local trio to take him on as an extra member, and the reformed ensemble called itself the Hoboken Four. In September 1935, the group appeared on Major Bowes’ famed “Amateur Hour” radio show, with Sinatra on lead vocal, and they were an instant success—though it was Sinatra who, in the months that followed, received most of the attention from audiences. It proved an intoxicating experience for the young singer, as well as a powerful catalyst. As John Lahr and other observers (including Sinatra’s close friend Shirley MacLaine) have noted, Sinatra immediately found in an audience what he wanted from his mother: a love that he could coax surely and that he felt he could trust. In some ways, Sinatra’s audience became his most significant love, though like nearly all the other loves that mattered to him, it was a relationship that would bring its share of failure, rancor, and deep hurt.

SINATRA BEGAN HIS professional life at a crucial time in the history of the entertainment arts. Advances in technology—including improvements in recording science, the influence of radio, and the spread of jukeboxes and home phonographs—were changing how music might be heard and preserved. The most important of these changes was a fairly recent one: the prevailing use of microphones by popular singers. It was a development that proved key to Sinatra’s success and art. In earlier years, singers had relied largely on their own force of projection or on a megaphone as a way to be heard over the band’s accompaniment. Those sorts of methods forced vocalists into high volumes, upper ranges, and sometimes unnatural tones. Belters like Sophie Tucker and Al Jolson used those limitations to a spectacular but showy effect. But as crooners like Rudy Vallee and Bing Crosby discovered, a microphone allowed a singer to draw closer to an audience’s ear and emotions. Indeed, a singer could now vocalize in the same intimate tone and manner that one might use while confiding to a friend, or to a lover in bed—and the effect of that new intimacy was electrifying to listeners. This made the mircrophone an instrument inseparable from the singer’s voice, and Sinatra was among the first artists who recognized the clear erotic (and later the artistic potential) of this valuable tool. In 1939, after he had left the Hoboken Four and was touring briefly with Harry James and His Orchestra, Sinatra was already beginning to improve his microphone technique. He moved the instrument close to his mouth in moments of romantic avowal, then pulled back from it when the music’s intensity increased. All the while he held on to the mike stand in a tender but unmistakably sexual manner.

But it was during his tenure with trombonist Tommy Dorsey’s big band that Sinatra made the most important strides in his early style. Dorsey could be a sublime soloist, playing musical passages that stretched for many bars in a smooth and continuous line, seemingly without pause for breath. Dorsey made it look effortless, and Sinatra studied the bandleader closely as he played, trying to figure out how he timed his breathing. Sinatra decided to model his own phrasing and breathing after Dorsey’s. He began taking long swims, holding and modulating his breath underwater as he played song lyrics in his head. After a few months, he redefined his phrasing. He was now able, like Dorsey, to execute long passages without a pause. “That gave the melody a flowing, unbroken quality,” he later said, “and that’s what made me sound different.”

By 1941, Sinatra had become Dorsey’s chief draw, and in that same year he won Billboard’s Best Male Vocalist award. He was singing in a manner that had not been heard before, and he was now eager to step outside of his role as a big band vocalist and establish himself as a solo artist. In 1942, Sinatra left Dorsey (“I hope you fall on your ass,” Dorsey told Sinatra). That same year, Benny Goodman and his orchestra were scheduled to play several December dates at New York’s Paramount, and the theater’s manager asked Goodman whether Sinatra could make a local appearance with the band. At first Goodman had no idea who Sinatra was. He ended up agreeing to the request, but he gave Sinatra last billing.

By the time of the opening show on December 30, 1942, a crowd of five thousand was crammed into the Paramount (Goodman and Sinatra performed several shows throughout the day). The audience was made up of mainly teenage girls, known as “bobbysoxers” for the white socks they favored. When Sinatra walked onstage, the theater exploded with the shrieks of young women. “What the hell was that?” Goodman asked, looking at Sinatra. The sound was so deafening that even Sinatra was momentarily stunned. Then he laughed, giddy at the thrill of it, stepped up to the microphone, wrapped his hands around the stand, leaned toward the crowd, and moved into “For Me and My Gal.” The pandemonium became so furious that, according to comedian Jack Benny, present that day, there were fears that the building might collapse. Come the end of the day, according to some reports, there wasn’t a dry seat in the house. It was the first sizable moment of adolescent pop culture fervor that America would see, and it became immediate sensational news around the country. When Sinatra returned to the theater two years later, the event set off a riot and provoked fights among Frank’s fans and detractors.

More than a decade later, Elvis Presley would duplicate—even extend—Sinatra’s feat with his early hits and his highly charged appearances on Tommy and Jimmy Dorsey’s “Stage Show” and the “Ed Sullivan Show,” and in 1964 the Beatles pulled off their own generation-defining breakthrough with their first performances on “Ed Sullivan.” But Sinatra’s astonishing emergence at the Paramount in 1942 was the event that opened up pop culture to new possibilities. At first, Sinatra’s burst of fame (like that of Presley and the Beatles) was greeted as a mass sensation—beguiling to some, alarming to others. It would be some time before the true drama and worth of his art, and its ability to stand for people’s hurts as well as their desires, would become known. Even so, many observers could see that Sinatra’s sudden and immense popularity would change American music. The big band era was effectively finished and a new era of pop vocal heroes was fast on its way. That shift would have a tremendous impact that lingers to this day—and nobody made that transition more possible, or would imbue it with as much artistic potential, as Frank Sinatra.

THE 1940S WERE an era full of big hopes and bigger perils. The nation had recovered from the long, devastating Depression of the 1930s, but it was now enmeshed in a high-stakes world war in Europe and Asia. In the midst of these years of risk—in this time of possible ruin or rebirth—America found its favorite voice in a fragile-looking romantic balladeer. No doubt part of what Frank Sinatra offered to his audience was the allure of a pleasant diversion during dark nights of uncertainty. But there was also something about the perceived vulnerability in the young singer’s voice and manner, and how it mixed with his clear longing, that spoke to and for many of those who elected him to his early popularity. Sinatra was a sign that America had a promising outlook: There were still great songs and exhilarating nights to come, and the last dance was a long way off. Or at least Sinatra’s own future looked fine. In 1943, he signed with Columbia Records. With the help of arranger Axel Stordahl, he recorded a remarkable series of graceful and inspiriting hits, including “All or Nothing at All,” “Where or When,” “These Foolish Things,” “Put Your Dreams Away,” “I’ll Never Smile Again,” “Day by Day,” “Someone to Watch Over Me,” “You Go to My Head,” “Try a Little Tenderness,” “(I Don’t Stand) A Ghost of a Chance,” “Nancy (With the Laughing Face),” and “That Old Black Magic.” Sinatra also appeared with Gene Kelly in a pair of key 1940s song-and-dance musicals, Anchors Aweigh and On the Town, and gave his first dramatic performance in the 1948 film The Miracle of the Bells. In 1944, Sinatra was a guest at President Franklin D. Roosevelt’s White House, and, in 1945, he won a special Academy Award for The House I Live In, a short film about racial bigotry and tolerance. At that time, nearly a decade before the civil rights movement would inflame and transfigure America, such a progressive stance from a popular entertainer was still uncommon, and the film’s message was among the reasons that several members of the press, various congressmen, and J. Edgar Hoover’s FBI termed Sinatra a communist.

Then, toward the decade’s end, Sinatra fell from grace—fast and hard. In part, the decline simply had to do with shifting musical tastes: In the exhilaration of the postwar period, a new audience wanted more verve than the light-voiced Sinatra now seemed capable of. In addition, Sinatra alienated many of his remaining supporters in a matter of personal conduct. In 1939, Sinatra had married his longtime girlfriend, Nancy Barbato, and the couple would have three children: Nancy Jr., Frank Jr., and Christina (Tina). But Sinatra had an eager eye, and there were rumors that he had seen numerous women during his road shows. When Sinatra began a steamy public affair with actress Ava Gardner, the press was outraged, and so were many of his fans. Sinatra divorced Nancy, and, in 1951, married Gardner. But within a few years, Sinatra’s relationship with both Columbia Records and his wife turned stormy, and in the seasons that followed, the singer lost everything—including his record and film contracts, his marriage with Gardner, and, perhaps most devastatingly of all, he lost his voice during a performance. After that, no record companies would take a chance on Sinatra. He was back to the club circuit, playing to meager audiences and trying to recapture the voice and confidence that had once come so readily.

In 1953, Capitol Records agreed to venture a one-year contract with Sinatra—if the artist was willing to pay his own studio costs. It was a somewhat degrading offer, but Sinatra took it—and by doing so, turned his life around. With his first few sessions for the label, Sinatra surprised both critics and former fans by flaunting a new voice that seemed to carry more depth, more worldly insight, and more rhythmic invention than the half-fragile tone that he had brandished in the 1940s. In addition, Sinatra became one of the first pop artists to take advantage of the possibilities offered by the new medium of long-playing records. LPs could hold over forty-five minutes of music in near-continuous play, which meant that a performer could sustain a mood, dwelling on it until that mood could give up no other revelations. Or, if the artist chose, he might even use the extended format to construct a character study or share an ongoing story. Sinatra brought these prospects to bear on his first full-fledged album for Capitol, In the Wee Small Hours, a deep-blue, hardbitten collection of soliloquies, portraying a man who rarely leaves his own aching memories, much less his room, unless it’s to find a 3 A.M. drink. In his Capitol years, Sinatra became, as vocalist and critic Mike Campbell later said, “the first true storyteller outside the blues singers. . . . The first guy to take those great standards and turn them into emotional experiences.”

With Wee Small Hours—which was conducted by Nelson Riddle, Nat “King” Cole’s up-and-coming arranger, who would become Sinatra’s greatest collaborator—Sinatra staked out the vocal sensibility that would become the hallmark of his mature style and that would establish him as the most gifted interpretive vocalist to emerge in pop or jazz since Billie Holiday. On the surface, Sinatra’s new style seemed almost more colloquial than musical. That is, he took supremely mellifluent material, like the title track, and sang it as if it were a hushed yet vital communication: a rueful confession shared with an understanding friend over a late-night shot of whiskey, or more likely, a painful rumination that the singer needed to proclaim to himself in order to work his way free of a bitter memory. In other words, Sinatra was now singing songs of romantic despair as if he were living inside the experience of those songs and as if each tune’s lyrics were his and his alone to sing. “It was Ava who did that, who taught him how to sing a torch song,” Nelson Riddle later told biographer Kitty Kelley. “That’s how he learned. She was the greatest love of his life, and he lost her.”

In effect, Sinatra’s stay at Capitol—along with the credibility he gained as an actor from his Oscar-winning performance in From Here to Eternity—proved to be the redemption of his career. Over the next ten years, he would record twenty-plus top-selling LPs for the label—alternating between sexy, uptempo, big band-style dance affairs and regretful musings on romantic despair and sexual betrayal—and he would also become one of the most consistently popular Top 40 singles artists of the 1950s. It was one of the richest and most successful growth periods that any pop artist has ever managed.

FRANK SINATRA WAS BACK on top and in better form than ever before. His new albums sold well and steadily, despite the rise of Elvis Presley and rock & roll. (Sinatra’s Only the Lonely stayed on Billboard’s charts for over two years, and his rave-up hard-swing triumph Come Dance with Me remained on the charts for nearly three years). Also, his complex dramatic work in Suddenly, The Man with the Golden Arm, Some Came Running, and Young at Heart—a surprisingly self-referential role as a bad-news depressive saloon singer—showed that Sinatra’s acting could be as dark and mesmerizing as his more serious musical efforts.

But Sinatra’s new success didn’t always bring out the best in him. He had long been known for a quick temper, and, like his mother, he didn’t easily relinquish grudges. In the late 1940s, when his career was on the skids, Sinatra insulted several high-placed columnists who he believed had been unfair in their coverage of him. He was particularly incensed by the writers who had made loud news about a misguided trip he made to Havana in 1947 to visit organized crime figure Lucky Luciano. Sinatra railed at several columnists, calling them whores; made veiled threats against others; and even sent one of the most influential gossip writers a tombstone with her name engraved on it. In one infamous episode, Sinatra punched a male columnist alongside the head for printing an innuendo that the singer was a communist. Sinatra was orded to pay a $25,000 fine for the incident. Sometime later, after the columnist died, Frank visited the writer’s grave and pissed on it.

Sinatra might have attributed some of this notorious behavior to the fury of youth or to the injury he felt as he watched his career plummet in the early 1950s and as he went through his intense, wrenching relationship with Ava Gardner. But the ill-famed bouts of wrath and boorishness continued after Sinatra’s rejuvenation in the early 1950s. There are numerous (and credible) stories of Sinatra flying into rages at friends and lovers, attacking parking lot attendants who didn’t place his car in a favored space, and even threatening to ruin Capitol Records—the label that helped place him back on top—when the company wouldn’t accommodate his plans for his own label. But perhaps the ugliest stories came from a close friend of Sinatra’s, actor Peter Lawford, who said he once saw Frank Sinatra hurl a young woman through a plate-glass window at a party. “[T]he girl’s arm was nearly severed from her body,” Lawford told biographer Kitty Kelley. (In one of Nancy Sinatra’s biographies of her father, she writes that Frank told her that the woman was extremely drunk and that she reeled back and fell into a window while being escorted from a party at his house. Sinatra, Nancy said, drove the woman to the hospital and covered her medical bills.) Lawford also claimed he saw Sinatra punch women on various occasions and once witnessed, in the Beverly Hills Hotel’s Polo Lounge, one of Sinatra’s sidekicks club a man with a heavy glass ashtray because Sinatra believed the man had said something disparaging about him. It was as if Sinatra, despite the beauty of his artistry and the brilliance of his commercial resurgence, felt he had to fight anew for every inch of his own domain—and that domain was wherever the singer allowed himself or his desires to roam.

In the late 1950s, Sinatra began to hold sway over a court of friends, singers, and actors who shared his tastes, views, and humor and who respected his luster. The group—which included Dean Martin, Judy Garland, Sammy Davis, Jr., and Peter Lawford (and which later included Joey Bishop and Shirley MacLaine)—had originally been an irreverent, anti-Hollywood enclave that gathered around Humphrey Bogart and his wife, Lauren Bacall. After Bogart’s death in 1957 (and following a brief failed affair between Sinatra and Bacall), Sinatra became the acknowledged center of the assembly. Under Sinatra’s custody, the Rat Pack turned into more than a celebrity clique—it became a demonstration of Sinatra’s new, well-protected way of life: high flying, hard living, and frequently unforgiving of those who crossed his will or temper.

But the Rat Pack’s most notable associate (in fact, something of a hidden member) was the one friend of Sinatra’s who would soon eclipse the singer’s fame and power: Massachusetts Senator John F. Kennedy. Kennedy had been a fan of Sinatra’s, and the two men met around 1959 as the senator was preparing for his 1960 campaign for the Democratic presidential nomination. Sinatra and Kennedy recognized that they shared a certain kindred sensibility: Both were fortunate descendents of aspiring immigrants, and both had a sense of personal entitlement, counterbalanced by social liberalism. Kennedy attended shows by Sinatra and the Rat Pack in Las Vegas, and Sinatra participated in Kennedy’s history in mixed but significant ways. Sinatra reputedly introduced Kennedy to Judith Campbell Exner, a woman who later claimed to be both Sinatra and Kennedy’s lover—though around the same time Sinatra was alleged to have introduced her to the mob boss Sam Giancana. (If true, this means that a major American politician and a major crime boss were sharing the same lover—and that Sinatra had orchestrated the nexus.) Sinatra also went to work for Kennedy’s presidential campaign and brought not only members of the Rat Pack into the cause but also a high-profile Hollywood contingent. But most important, according to some writers, Sinatra persuaded mob forces to turn out the vote for Kennedy in crucial districts of Chicago during the senator’s incredibly tight race against the Republican candidate, Richard Nixon. In other words, Frank Sinatra won John Kennedy the presidency and helped secure his lasting place in the country’s history.

Sinatra hosted one of Kennedy’s Inaugural Balls and escorted Jacqueline Kennedy to the event, and for a time he had a favored access to the most powerful and illustrious figure in America. This proved useful when Sinatra wanted to make a film out of the novel The Manchurian Candidate, the theme of which was a plot to assassinate a presidential candidate. The studio, United Artists, was squeamish about the content. At Sinatra’s request, Kennedy—who had enjoyed the novel—intervened, and the film went into production. (After Kennedy was assassinated in November 1963, Sinatra forbade the film’s rerelease. As a result, one of America’s greatest postwar movies—and Sinatra’s last meaningful acting work—stayed out of circulation for twenty-five years.)

The good times between Sinatra and Kennedy didn’t last long. In 1962, Attorney General Robert Kennedy’s investigation of organized crime turned up more reports of Sinatra’s affiliation with known racketeers. In particular, Robert Kennedy was disturbed by Sinatra’s friendship with mob leader Sam Giancana and advised Sinatra to break off any such ties (the attorney general didn’t know about Exner’s tie to Giancana and the president). Sinatra declined the advice. A short time later, John Kennedy canceled a planned visit to Sinatra’s Palm Springs home and stayed instead at the home of Bing Crosby. After hearing the news, Sinatra took a heavy hammer to the airplane tarmac he had installed for the president’s arrival. He was hurt and enraged and reportedly felt he had been shunted aside and betrayed by a man he had befriended and helped. Although Kennedy and Sinatra continued communications on a less frequent and more discreet basis, Sinatra never again placed himself in such an unprotected and mortifying position.

THE 1960S PROVED a variable time for Frank Sinatra. He enjoyed several Top 40 hits (including “It Was a Very Good Year,” “Strangers in the Night,” “Summer Wind,” “That’s Life,” and the vainglorious “My Way”) and made a steady stream of albums for his new label, Reprise (among the better ones: I Remember Tommy, Sinatra and Basie, September of My Years, and Sinatra at the Sands). But as time passed, Sinatra found himself and his musical tradition displaced by pop music’s shifting aesthetic. In the 1950s, Elvis Presley and the rise of rock & roll brought new styles, values, and vigor into the mainstream, and Sinatra decried this development, terming rock & roll a music of bad manners and low skill. “It is sung, played, and written for the most part by cretinous goons,” he said in 1957, “and by means of its almost imbecilic reiterations and sly, lewd—in fact, plain dirty—lyrics, it manages to be the martial music of every sideburned delinquent on the face of the earth.”

In the early 1960s, the music and songwriting of the Beatles and Bob Dylan caused even greater change, in effect killing off the Tin Pan Alley and Broadway traditions that had provided earlier pop singers like Sinatra with their repertoire. For a time, Sinatra seemed to be casting about for a new manner and a new purpose. In July 1966, at age fifty, Sinatra married actress Mia Farrow, age twenty-one. Their love was genuine and ardent, though some thought that the union was an attempt by Sinatra to regain a bit of his youthful vitality and relevance. After two years, Sinatra tired of the relationship. While Farrow was filming Rosemary’s Baby, Sinatra sent a lawyer to her set with divorce papers. Sinatra had not told her himself that he intended to end the marriage.

In June 1971, unhappy with his career and his personal life, Frank Sinatra withdrew from the entertainment business at age fifty-five. But the retirement didn’t last. In fact, he played concerts for political benefits during his layoff period. (By this time, Sinatra had switched his political affiliation. He was now a proponent of Republican California Governor Ronald Reagan as well as a supporter of the Richard Nixon-Spiro Agnew Administration. Some observers thought Sinatra’s political shift was a final revenge for his disappointing Kennedy experience.) In 1973, Sinatra returned to the pop world with Ol’ Blue Eyes Is Back and also returned to the touring life. In 1976, he entered his fourth marriage, to Barbara Marx, the former wife of Zeppo Marx. The marriage would last.

Sinatra continued to record and perform into the 1990s. Most of his late records showed him still looking for a fresh sound. Over the years, he made some passing concessions to the new pop forms; in 1966, he enjoyed a Top 10 hit with his roaring Ray Charles-style “That’s Life,” and he recorded affecting versions of Elvis Presley’s “Love Me Tender” and George Harrison’s “Something” for the 1980 album Trilogy. He also periodically covered songs by Paul Simon, John Denver, and Billy Joel. But by and large, the newer material he selected rarely suited his prime strengths, such as the way he could inhabit a song’s words, turning them into an urgent personal disclosure, or the way he could ride a lyric’s rhythm and melody with a spry, buoyant wit. One longed to hear what Sinatra might do with more fitting modern songs, like Sam Cooke’s “Mean Old World,” Mick Jagger and Keith Richards’ “The Spider and the Fly,” Van Morrison’s “Moondance,” Randy Newman’s “Lonely at the Top” and “Sail Away,” or Elvis Costello’s “Shipbuilding,” but we never got to find out. In concert, he continued to favor his old repertoire, and he also continued to sing it better than anybody.

Even so, Sinatra could still tap an occasional pop nerve. In 1980, he found a brash new anthem in “Theme from New York, New York”—a spirited song about tenacity that has been a favored item on barroom jukeboxes for the last eighteen years. And in 1993 and 1994, Sinatra enjoyed multiplatinum hits with Duets and Duets II, which paired Frank’s vocals with performances by Aretha Franklin, U2’s Bono, Barbra Streisand, Natalie Cole, Liza Minnelli, Tony Bennett, Patti Labelle, Linda Ronstadt, Chrissie Hynde, Willie Nelson, Neil Diamond, Jimmy Buffett, Gladys Knight, and Lena Horne, among others. For a brief time in 1993, Duets was second on Billboard’s charts—a notch below Snoop Doggy Dogg’s Doggystyle.

Sinatra received a Lifetime Achievement Award at the 1994 Grammy ceremony in New York. The honor represented an autumnal triumph and a valuable reconciliation of sorts. In the 1960s and 1970s, Sinatra had been anathema to many young pop fans, not just for exemplifying the classic prerock American Songbook tradition but also for seeming to embody a lifestyle of luxury and hubris. But in time that disregard faded and many listeners and musicians came to discover and appreciate, on their own terms, the depths and smarts in Sinatra’s artistry. Also, many modern music fans now understood that Sinatra’s spirit of bravado and impiety wasn’t all that far apart from the spirit of rebellion that characterized early rock & roll and much of the music that followed. In effect, Sinatra—with his defiance and his disrespect for phoniness—had been a counterculture unto himself for most of his career. Sixty years after he exploded the pop world, Frank Sinatra was once again a paradigm of hip discernment. U2’s Bono introduced the aging singer to the New York Grammy audience, and Sinatra was moved to tears by the standing ovation he received. But as he attempted to speak about his life, the orchestra abruptly cut him off when one of Sinatra’s employees feared he was rambling and looking confused.

A week later, at a concert in Richmond, Virginia, Sinatra collapsed and was taken off the stage in a wheelchair. He toured some more after that, but he was beginning to miss lyrics (even with the aid of TelePrompTers) and to overshoot his timing. At moments, he seemed lost on the same stages that had once been his lifelong familiar home. He gave a final concert at his 1995 Palm Springs Golf Tournament benefit; his last full song in public was “The Best Is Yet to Come.” In December of that year, he appeared as guest of honor at an eightieth birthday celebration event that featured performances by Bruce Springsteen, Bob Dylan, Ray Charles, Little Richard, Salt-n-Pepa, Tony Bennett, Vic Damone with Steve Lawrence and Eydie Gorme, and others. At evening’s end, the tribute performers brought Sinatra onstage during “Theme from New York, New York” and somebody handed him a microphone. As the song came to its close, Sinatra pounced on the final phrase, “New York, New York,” sustaining and holding his tone with such a fierce sureness that his face turned red before he released the final note. Then, refusing any help, he made his way off the front of the stage, into the company of his wife and family, and he was gone from America’s eyes.

FRANK SINATRA LEFT BEHIND a vast body of tangible and enduring work—over two hundred albums, sixty movies, well over two hundred hours of live television, and at least an additional two hundred full concert appearances that have been preserved on film and video. But as remarkable and valuable as that legacy is, we will never again be able to sit in a theater and watch Frank Sinatra walk onto a stage, and it is Sinatra’s art as a live performer that, I suspect, is what will be missed the most.

I recall seeing him several times in the 1970s, 1980s, and early 1990s at various West Coast venues—including the Universal Amphitheatre in Los Angeles—and in Las Vegas. He would walk onstage in a brisk, matter-of-fact stride, wearing a crisp black tuxedo and a bright, cocksure expression. The audience would react with cheers and whistles and squeals—just as bobbysoxers had done decades earlier—and even if the acclaim came as no surprise, he always appeared thankful in that indomitable way of his. In each of these shows, Sinatra used the occasion of his opening song to trumpet his arrival as a triumph, often with a boastful or brassy song, like “Theme from New York, New York,” “Fly Me to the Moon (In Other Words),” or Harold Arlen and Ted Koehler’s “I’ve Got the World on a String”—the song he picked as his first Capitol single in the 1950s to proclaim his regeneration: “I’ve got a song that I sing/I can make the rain go/Anytime I move my finger. . . . ” In those moments, Sinatra relied entirely on his voice to depict whatever ambition and pride he might bring to a stage.

To be sure, Sinatra’s voice on those occasions was showing signs of wear. His range had lowered considerably, his tone had darkened, and his purity had turned rawer and rougher—and yet in some ways those flaws made his voice all the more affecting. In particular, in his delivery of ballads he sounded closer to the grain of heartache and desolation—a bit less proud, more wistful or abject than before. One night he offered a medley: a thoughtful mating of Harold Arlen and George Gershwin’s “The Gal That Got Away” and Richard Rodgers and Lorenz Hart’s “It Never Entered My Mind.” It showcased Sinatra at the full extent of his affecting interpretive power: prowling the shadowy fringes of the stage with cigarette in hand, letting the signs of age in his voice—the brandy-tone timbre, the grainy legato—infuse the lyric: “The night is bitter/The stars have lost their glitter/The winds grow colder/And suddenly you’re older/And all because of a gal who got away.” He sang the words in the manner of a broken, brooding man who knew he had lost his last glimpse of love’s saving whims and could only ruminate over all the tenderness that was now so painfully and finally out of reach. I remember thinking at the time that it didn’t matter that the portrait jarred with everything we presume about the real Sinatra—it just mattered that Sinatra had the sensibility to make us believe it was real. Looking back, I’m not so sure that we weren’t seeing the real Sinatra after all.

In his 1963 Playboy interview, Sinatra said: “I’m for anything that gets you through the night, be it prayer, tranquilizers, or a bottle of Jack Daniel’s.” In 1997, Charlie Rose hosted a roundtable discussion by four men who had met or written about Sinatra and somebody mentioned how Sinatra often liked to stay up through the night, talking to friends, maybe nursing a drink, until dawn rose. Sinatra saw those mornings as a “victory,” said author Bill Zehme—as a way of beating the dark.

In truth, though, Sinatra’s greatest victories were achieved in the dark—the dark of studios and the dark of evenings in clubs, concert houses, and lounge bars. Night after night, for more than sixty years, Frank Sinatra stood onstage and sang songs about love and longing, about hope and despair, and each time he did so, he communicated the emotional truths of those songs to a mass of strangers as if that mass were a handful of understanding intimates. Chances are, he was not doing this merely for the money; long ago, Frank Sinatra became rich enough to live in any world he wanted to build for himself. Instead, maybe he did it simply because somehow singing those songs enriched him, helped him realize a depth and compassion that did not come quite so easily in the realities of his daily private life. Or perhaps singing simply became his most reliable companion—the best way of forestalling the darkness. Maybe it was his way of driving death back: As long as he performed on a stage, he was alive—and he could be the best man he knew how to be.

Frank Sinatra sang in and from the darkness. He sang about a profound loneliness that he knew well and that he spent his whole life trying to beat, in both wondrous and awful ways. Just as important, Sinatra sang to the loneliness inside others—and those who heard that voice sometimes found something of their own experience within its resonance and then—maybe—found some solace and courage as well. Sinatra’s voice entered our dreams, illuminated our pains and hopes, longer than any voice we have ever known before or may ever know again. That voice was the voice of our century, and now it sings no more, except in history.