What will Frank Sinatra be remembered for? In the decade prior to his retirement in 1995, his singing became a grotesque and embarrassing self-caricature. His oft-reported ties to organized crime have figured prominently in the tabloids for years. And then there are the various cults that have formed around him. His most passionate fans, obsessed with his charismatic manner, celebrate his best singing and his worst indiscriminately. Meanwhile, another cult, a cottage industry of scholars specializing in “cultural studies,” neglects his art to focus on his status as an “iconic” figure in American popular culture; a conference to be held next year at Hofstra University on Frank Sinatra: The Man, the Music, the Legend, is typical of the breed.
From the sorts of papers that are likely to be delivered at such a conference, as from the state of Sinatra’s reputation elsewhere, one would hardly suspect that he really deserves to be remembered as, in the words of the music critic John Rockwell, “the greatest singer in the history of American popular music.” Among those whose professional judgment counts, moreover, Rockwell is hardly alone. In 1956, the jazz critic Leonard Feather polled 120 noted musicians, asking them to name their all-time favorite singer. Sinatra received 56 votes; the runner-up, Nat Cole, received 13. Some of the musicians who put Sinatra at the top of their lists were Miles Davis, Duke Ellington, Stan Getz, Benny Goodman, Gerry Mulligan, Oscar Peterson, Lester Young—and Nat Cole.
What did these great jazz musicians admire about Sinatra? No doubt some were fascinated by his public personality; but in the end, a musician is significant only to the extent that he succeeds in expressing his personality through music. Sinatra’s ability to do this, and not his tempestuous love life or (to quote the Hofstra conference’s “call for papers”) his “multigenerational presence,” is what alone gives him a continuing claim on our attention.
Born in 1915 in Hoboken, New Jersey, Frank Sinatra made his first recordings in 1939.1 Four short years later, he was one of the most famous men in America, hugely successful both as a singer and as a screen actor, adored by countless teenage girls and esteemed by his colleagues, all of whom unhesitatingly acknowledged his preeminence. “I know it sounds like something out of a B movie,” recalled Jo Stafford, who sang with Sinatra from 1940 to 1942 in the big band of the trombonist Tommy Dorsey, “but it’s true: before he’d sung four bars, we knew. We knew he was going to be a great star.”
Sinatra’s recordings with Dorsey may seem, on first hearing, not to justify his youthful celebrity. Such songs as “I’ll Never Smile Again” reveal a light, lyric baritone voice and an exceptional command of legato: the individual notes in each phrase are bound together seamlessly, and shaped with perfect taste. (“He sings with such a beautiful legato!” the music critic Virgil Thomson once remarked admiringly.) But most big bands featured “boy singers” with attractive baritone voices, all of them, like Sinatra himself, influenced by Bing Crosby, the dominant popular singer of the 30’s. If Sinatra’s earliest recordings do not strike today’s listeners as notably original in style, that is because we tend to forget that by 1942, he was already well on the way to replacing Crosby as the most frequently imitated male singer of the day.
Sinatra’s youthful style, in other words, no longer sounds individual because it has long since become the lingua franca of popular singing. But in 1939, as the jazz singer Joe Williams has pointed out, no one was singing like Sinatra:
I loved the way he sang, the way he phrased. I could understand the lyric. He had found an unusual sound quite unlike anybody I had heard before. . . . He listened to Tommy [Dorsey], and he tried to sing the way Tommy played: to assimilate the breathing technique so that everything [in the lyric] was tied together in a narrative, so that you could understand what was happening.
This last observation is crucial to understanding Sinatra’s main contribution to the art of popular singing: he phrased with a conscious regard for the logic of the lyric. As he once told an interviewer:
It’s important to know the proper manner in which to breathe at given points in a song, because otherwise what you’re saying becomes choppy. For instance, there’s a phrase in the song “Fools Rush In” that says, “Fools rush in where wise men never go/But wise men never fall in love/So how are they to know?” Now that should be one phrase because it tells the story right there. But you’ll hear somebody say, “Fools rush in,” and breathe, “Where wise men never go”—breath—“But wise men never fall in love. . . .” But if you do it [in one breath], that’s the point, you’ve told the whole story.
That this approach was not merely a technical innovation but a key feature of Sinatra’s interpretative approach becomes more obviously apparent in the solo recordings he began making for Columbia in 1943, most of them featuring the romantic orchestral arrangements of Axel Stordahl. Unlike Bing Crosby, whose informal singing style was notable for its relaxed, jazz-inflected air and its comparatively narrow expressive range, Sinatra recorded mostly ballads, often sung at very slow tempos and usually accompanied by medium-sized string sections. In these ballads, moreover, he “read” the lyrics with uncanny clarity and emotional directness. His phrasing communicated that directness, and made him stand out as among the first popular singers to take seriously the sentiments embodied in the songs he sang.
Sinatra’s word-conscious approach was ideally suited to the songs of the 30’s and 40’s. Ira Gershwin, Lorenz Hart, Johnny Mercer, and Cole Porter, all of whom had been deeply influenced by the light verse of 19th-century craftsmen like W. S. Gilbert, brought to the art of popular song-writing an unprecedented degree of sophistication, and Sinatra was early to grasp the significance of their achievement. “I’ll leave the music to somebody else,” he once said. “I pick the lyrics.”
To be sure, the young Sinatra had not yet learned how to illuminate fully the subtleties of the more emotionally complex lyrics of the period; his early recordings of such Johnny Mercer lyrics as “Laura” and “One for My Baby” are painfully naive by comparison with the versions he re-recorded in the 50’s. Moreover, his voice, though already lovely, was still immature, and his sense of swing would remain undeveloped for another decade or so, causing him to sound awkward and uncomfortable in uptempo numbers.2 He was at his best in simple, straightforward ballads like Hoagy Carmichael’s “The Nearness of You,” recorded in 1947; his unaffected sincerity and sustained legato line in this song still move listeners a half-century later.
The course of Sinatra’s career took a sharp downward turn as he entered his mid-thirties. He was no longer young enough to be considered a “boy singer,” or to be dramatically credible in juvenile roles like the ones he had played successfully in the movies Anchors Aweigh (1945) and On the Town (1949). In 1950, he suffered a vocal crisis, possibly brought on by the stresses of his complicated private life. (Sinatra divorced his first wife the following year in order to marry the actress Ava Gardner, who left him shortly thereafter.) By 1952, he had been dropped by both Columbia and MGM, and was out of work and in debt.
Characteristically, Sinatra’s response was to reinvent himself. Putting his juvenile persona behind him once and for all, he accepted a supporting role in the 1953 film of James Jones’s war novel, From Here to Eternity, for which he won an Oscar.3 He then signed a contract with Capitol Records, hired Nelson Riddle as his chief arranger, and developed a new singing style whose appeal to 50’s audiences was as powerful as his youthful crooning had been in the 40’s.
The new Sinatra was a mature Sinatra. Not only had his voice grown darker and more characterful, but he also had a larger fund of emotional experience on which to draw, and his artistry deepened as a result. Though his taste in songs had always been good, he now concentrated primarily on first-rate standards; though he had long been musically painstaking, he now took still greater care in crafting his interpretations. Nelson Riddle, perhaps the finest arranger ever to work in the field of popular song, fashioned uniquely challenging musical settings for him, and in response, Sinatra created a fully adult alter ego to sing the “saloon songs” he loved. This persona—almost certainly based in part on the character Humphrey Bogart played in The Maltese Falcon and Casablanca—was a man who had been unlucky in love, and who was recounting his sufferings candidly and unsentimentally.
Sinatra’s musical growth is thrown into high relief by comparing his two recordings of the Jule Styne-Sammy Cahn torch song, “Guess I’ll Hang My Tears Out to Dry.” The first, made for Columbia in 1946, is a tasteful performance which does little more than skim the surface of the song. The second, made for Capitol in 1958, is pensive and subdued yet intensely dramatic, rising to an expansive climax in which Sinatra sings an open-throated, beautifully placed high E-flat. Riddle’s orchestral accompaniment, reminiscent of Maurice Ravel in its deployment of instrumental color (and conducted with remarkable rhythmic flexibility by Felix Slatkin, first violinist of the Hollywood String Quartet), adds immeasurably to the total effect of Sinatra’s singing, which is overwhelming in its impact.
The Capitol recording of “Guess I’ll Hang My Tears Out to Dry” also illustrates another feature of Sinatra’s mature style: the underlining of individual words and phrases for dramatic emphasis. In 1946, Sinatra “read” Sammy Cahn’s lyric in a smooth, evenly produced manner; in 1958, the vocal production is no less even (indeed, the climactic phrase is actually longer), but the buttery smoothness has given way to a detailed lyricism in which dynamics and tone color change subtly from phrase to phrase in response to the unfolding of the “story.”
This recording is part of Sinatra’s greatest album, Only the Lonely, a collection of twelve ballads which represents the high-water mark of postwar popular singing. Especially in “Guess I’ll Hang My Tears Out to Dry,” “It’s a Lonesome Old Town,” “Spring Is Here,” and “One for My Baby,” Sinatra attains a degree of vocal refinement and interpretative subtlety worthy of comparison—yes, I will say it—with a classical recitalist like the German baritone Dietrich Fischer-Dieskau. Each song is turned into a one-man, one-act dramatic monologue in which the music carries the words, precisely in the manner of Fischer-Dieskau’s performances of such art songs as Franz Schubert’s Erlkönig or Hugo Wolf’s Anakreons Grab. Yet vocal beauty is never subordinated to the demands of dramatic logic: Sinatra’s legato remains pristine throughout.
While there are other, equally valid ways to sing popular songs—including the lighter, more dispassionate style of singers like Crosby, Fred Astaire, and Ella Fitzgerald—Frank Sinatra’s mature style proved so compelling that it left its stamp on nearly every well-known male pop singer of the 50’s. Only those singers who (like Mel Tormé) were deeply influenced by jazz, or whose voice types bore no resemblance to Sinatra’s dark, viola-like baritone (as was the case with Tony Bennett), were able to escape his influence.
But Sinatra’s style also contained the seeds of its own eventual decadence. At its best, his highly dramatic singing was carefully balanced between restraint and exhibitionism—a balance he seems to have found it difficult to strike outside the tightly controlled environment of the recording studio. In concert, both in the singing itself and in his on-stage patter, he tended to lapse into a crowd-pleasing vulgarity astonishing in so sensitive a musician. “He sings with the grace of a poet,” the trombonist Milt Bernhart once said, “but when he’s talking to you, it’s New Jersey.” Only in the studio was he completely and consistently himself.
That self became harder to locate as rock-and-roll transformed American popular music beyond recognition. Starting in the mid-60’s, Sinatra attempted with limited success to reinvent himself yet again for a new generation of listeners, working with such rock-oriented musicians as Jimmy Bowen (who would become famous a quarter-century later for his work with Garth Brooks and other country singers). Though he also continued to look for new material compatible with his essential musical seriousness—he was among the first American popular singers, for example, to perform the work of the Brazilian composer Antonio Carlos Jobim—many of Sinatra’s recordings of the 60’s revealed a growing loss of artistic direction, and in 1971 he announced his retirement.
When he resumed performing in 1974, he deemphasized recording in favor of public appearances, having learned that he could still fill large auditoriums with his aging but loyal fans. But like those fans, Sinatra too was growing older, and no sooner had he begun to perform in public again than it became clear that his voice was in decline—a natural development for a man of nearly sixty, but one he was apparently incapable of accepting. The decline was slow at first, but by the time he finally retired for good, a few months before his eightieth birthday, his worst performances had done his musical reputation a good deal of harm.
Fortunately, this final phase of Sinatra’s career has begun at last to recede from view, and it has also become easier with the passage of time to ignore the gargoyle-like Mafioso manqué of tabloid myth in favor of the master, musician who (in Mel Tormé’s admiring words) “held the patent, the original blueprint on singing the popular song.”
Not that it will ever be possible, or even necessarily desirable, to ignore completely the tawdry side of Frank Sinatra: his vulgarity is part of his mystery. But it is only in the pure light of his singing that the unsavory aspects of his long and eventful life remain visible. No other singer has done more to widen the expressive horizons of American popular song, and none has been more widely admired or influential. It is the consummate artistry of the man who recorded such classic albums as Only the Lonely and In the Wee Small Hours that will be remembered long after everything else about him is forgotten, or has become grist for the mills of gushy journalists and clueless professors.
A Select Discography
Few singers, whether popular or classical, have recorded so extensively over so long a period of time as Sinatra, who cut his first 78 in 1939 and taped his last CD in 1994. He is thought to have made some 1,800 recordings, including multiple versions of many songs (eight different performances of Cole Porter’s “Night and Day” have been commercially released to date). Virtually all of his studio recordings are now available on compact disc. Here are some of the best:
1939-42: Sinatra’s earliest commercial recordings were made with the big bands of Harry James and Tommy Dorsey. “All or Nothing at All,” performed with James in 1939, is part of Portrait of Sinatra: Columbia Classics (see below). Frank Sinatra & Tommy Dorsey: Greatest Hits (RCA Victor 09026-68487-2) is a budget-priced compilation of fifteen of the most popular Sinatra-Dorsey sides, including “I’ll Never Smile Again.”
1943-52: The Columbia Years, 1943-1952: The Complete Recordings (Columbia/Legacy CXK 46873, 12 CD’s) includes all 285 songs Sinatra did for Columbia (including numerous unissued sides), heard in exceptionally clear-sounding digital transfers from the original 78’s and master tapes. Dozens of albums drawn from this body of work have been released by Columbia over the years, of which the most recent and representative is Portrait of Sinatra: Columbia Classics (Columbia/Legacy C2K 65244, two CD’s), a 36-track anthology in which such performances as “The Nearness of You” and the first version of “Guess I’ll Hang My Tears Out to Dry” can be heard in the same excellent transfers originally made for The Columbia Years.
1953-59: Sinatra was at his vocal and artistic peak in the studio albums he made for Capitol during the 1950’s, the best of which are In the Wee Small Hours (Capitol CDP 7 46571-2), Close to You (CDP 7 46572-2), Songs for Swingin’ Lovers! (CDP 7 46570-2), and Only the Lonely (CDP 7 84471-2, including the second versions of “Guess I’ll Hang My Tears Out to Dry” and “One for My Baby”), all arranged by Nelson Riddle; Come Dance With Me (CDP 7 48468-2), arranged by Billy May; and Where Are You? (CDP 7 91209-2, including the second version of “Laura”), arranged by Gordon Jenkins. These six CD’s form the core of Sinatra’s recorded legacy.
1960-71: Starting in 1960, Sinatra began recording for Reprise, his own label. These albums were generally less interesting than the ones he made for Capitol, in part because Sinatra’s choice of material grew increasingly erratic. But he can be heard at the top of his form on Sinatra & Strings (Reprise 9 27020-2), arranged by Don Costa; Sinatra and Swingin’ Brass (9 27021-2) and Sinatra-Basie (1008-2), both arranged by Neal Hefti, the latter featuring the big band of Count Basie; and Francis Albert Sinatra & Antonio Carlos Jobim (1021-2), arranged by Claus Ogerman. Also of interest is The Reprise Collection (9 26340-2, four CD’s), an 81-track anthology which contains a cross-section of Sinatra’s best work for Reprise, including a number of outstanding performances otherwise available only on inferior albums.
1973-84: When Sinatra resumed performing and recording in 1973, his voice was already starting to show signs of technical decline, and none of his post-retirement albums is of consistently high quality. (Several of the better performances from this period are included on The Reprise Collection, above.) Sinatra made no commercial recordings between 1986 and 1993, when he was unwisely persuaded by Capitol to return to the studio for Duets (Capitol CDP 89611-2), an album which, though a great popular success, is of no musical interest whatsoever and reveals his voice to be in an advanced state of decrepitude.
1 No factually reliable full-length biography of Sinatra has yet been published. The best short treatment of his life and work is John Rockwell’s Sinatra: An American Classic (1984); also of interest is Gene Lees’s “The Sinatra Effect,” an insightful essay reprinted in Lees’s Singers and the Song (1987). The most useful books about Sinatra to appear in recent years are The Frank Sinatra Reader (Oxford, 297 pp., $27.50), a collection of essays edited by Steven Petkov and Leonard Mustazza, and Will Friedwald’s Sinatra! The Song Is You (Scribner, 557 pp., $30.00), an uneven and overpersonal but nonetheless informative survey of Sinatra’s singing career. Sinatra’s recordings themselves are discussed in the discography at the end of this article.
2 Though such later albums as Songs for Swingin’ Lovers show how Sinatra developed into a self-assured and impressively accomplished “rhythm singer,” he was never a jazz singer in the true sense of the term. “The difference between Frank and me,” Nat Cole once remarked acutely, “is that the band swings Frank, and I swing the band.”
3 Though Sinatra’s acting career is beyond the scope of this essay, it should be noted that while most of the movies he made in the 50’s and 60’s were second-rate or worse, his performances in such films as From Here to Eternity, The Man With the Golden Arm (1955), and The Manchurian Candidate (1962) were widely admired by critics and colleagues. Shirley MacLaine spoke for many when she described Sinatra as “about as naturally talented as anybody I’ve ever known in my life,” though she also deplored his unwillingness to “work harder at what he’s doing.”