An Appreciation of Frank Sinatra: 1915-1998

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The 1960s proved a variable time for Frank Sinatra. He enjoyed several Top Forty 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 Reprise, the label he had started (among the better ones: I Remember Tommy, Sinatra 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 had 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 tradition 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 the set with divorce papers.

In June 1971, unhappy with his career and his personal life, Frank Sinatra withdrew from the entertainment business. But the retirement didn't last. In fact, he gave 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 Gov. Ronald Reagan, as well as a supporter of the Richard Nixon-Spiro Agnew administration. Some observers thought that Sinatra's 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 show 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 Ten hit with the roaring Ray Charles-style "That's Life," and he recorded affecting versions of Elvis Presley's "Love Me Tender" and the Beatles' "Something" in 1980. He would also cover songs by Paul Simon, John Denver and Billy Joel. But by and large, the newer material that Sinatra selected rarely suited his prime strengths, such as the way he could turn a song's words 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," 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 past eighteen years. In 1993 and 1994, Sinatra enjoyed multiplatinum hits with Duets and Duets II, which paired Frank's vocals with performances by Aretha Franklin, Bono, Barbra Streisand, Liza Minnelli, Tony Bennett, Patti LaBelle, Chrissie Hynde, Willie Nelson, Neil Diamond, 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 pre-rock American-songbook tradition but also for seeming to embody a lifestyle of luxury and hubris. But in time that disregard had faded, and many listeners and musicians came to 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 defiance 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. Sixty years after he exploded the pop world, Frank Sinatra was once again a paradigm of hip discernment. 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 because one of Sinatra's employees had 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 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, Tony Bennett 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 last 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  more than 200 albums and collections, sixty movies, well over a hundred hours of live television and at least an additional 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 early 1980s at the Universal Amphitheater, in Los Angeles. He would walk onstage with 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 bobby-soxers had done four 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."

To be sure, Sinatra's voice in those days 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 his delivery of ballads, in particular, he sounded closer to the core of heartache and desolation  a bit less proud, more softened or abject than before. One night he offered a medley: a thoughtful mating of Harold Arlen and Ira 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." Charlie Rose recently hosted a round-table 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. They said that Sinatra saw those mornings as a "victory"  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 to 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.

This story is from the June 25th, 1998 issue of Rolling Stone.

To read the new issue of Rolling Stone online, plus the entire RS archive: Click Here

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