For virtually any American over the age of sixty, Bing Crosby’s name is likely to evoke a wide range of memories. Though he was by far the best-known popular singer of the pre-rock era, Crosby was also a full-fledged movie star who won a best-actor Oscar for Going My Way (1944) and easily held his own opposite the likes of Fred Astaire and Bob Hope in such lighter fare as Holiday Inn (1942) and The Road to Morocco (1942). His radio shows were no less successful, and with the arrival of TV in the 50’s, his face became as familiar a fixture in American homes as was his easygoing bass-baritone voice.

Bing Crosby: A Pocketful of Dreams, the first installment of a two-volume biography by the jazz critic Gary Giddins,1 contains a list of statistics conveying something of the extent to which Crosby once dominated American popular culture. According to Giddins:

  • He made more recordings than any other singer, of which 38 were number-one hits, more than any other popular artist. (The Beatles, by contrast, topped the charts only 24 times.)
  • By 1980, he had sold a total of 400 million discs.
  • He was one of Hollywood’s top ten box-office attractions in America in fifteen different years between 1934 and 1954.
  • His best-known radio program, NBC’s Kraft Music Hall, reached an audience of as many as 50 million listeners—at the time, well over a third of the entire U.S. population.

But Crosby’s fame did not long survive his death in 1977. Indeed, it is now difficult to find anyone under the age of forty who knows anything specific about him other than that he recorded Irving Berlin’s “White Christmas.” By and large his work is available only on hard-to-find CD’s released by independent European labels, while most of his films are long forgotten. A four-CD box set containing a representative but not always musically satisfying cross-section of Crosby’s recordings for Decca is currently the only large-scale reissue on a major American label.2 (It can be purchased online by viewing this article on COMMENTARY’s website, The only single-CD compilation of the best of Crosby’s important early recordings is Bing Crosby: 1926-1932 (Timeless CBC1-004), an impeccably produced Dutch import which is poorly distributed in this country but can sometimes be obtained online from, a mail-order firm that also stocks a wide assortment of other Crosby reissues on independent labels.

Though several other artists of his generation—Louis Armstrong, Duke Ellington, and Benny Goodman among them—continue to be widely recognized as key figures in American music, Crosby tends increasingly to be overlooked by critics and journalists. He was, for instance, omitted entirely from Ken Burns’s ten-part PBS series Jazz, and is mentioned only in passing in Geoffrey C. Ward’s companion volume to the series.

How could so bright a star have dimmed so fast? Was there less to Bing Crosby than met the ear? Gary Giddins thinks not, and in A Pocketful of Dreams he makes the case for Crosby in unprecedentedly rich and rewarding detail. Though certain chapters could have been trimmed to useful effect (many readers will feel, for example, that far too much space is devoted to Crosby’s less important films), the book as a whole is both finely written and thoroughly engrossing. Still, in telling the story of how Crosby became “a phenomenon in the cultural life of the United States,” A Pocketful of Dreams occasionally dwells on the phenomenon at the expense of the artist.

Giddins is not himself a musician, trained or otherwise; for all his evident appreciation of Crosby’s singing, he lacks the technical knowledge needed to explain fully what he is hearing. And though his discussion of the posthumous decline in Crosby’s reputation is plausible as far as it goes, he is similarly unable to supply a completely adequate musical explanation for why “the most influential and successful popular performer in the first half of the 20th century” should have faded into semi-obscurity a mere quarter-century after his death.



Born in 1903 in Tacoma, Washington, Harry Lillis Crosby, Jr., was the fourth of seven children of a charming but lazy bookkeeper and a cold, manipulative woman who demanded that, unlike their ne’er-do-well father, her children get ahead in the world. The Crosbys moved to Spokane in 1905, and Bing (he acquired his nickname because of his liking for The Bingville Bugle, a humorous newspaper supplement of the time) spent eight years attending the Jesuit-run Gonzaga High School and University, where he received a Catholic-style classical education, doing well at both Greek and Latin.

Crosby’s background explains much about the complicated man he became. The happy-go-lucky “regular guy” who bantered amiably on screen with Bob Hope and Dorothy Lamour was in real life highly intelligent and well-read (in a 50’s interview, he casually mentioned having recently read novels by James Gould Cozzens, John P. Marquand, and Evelyn Waugh). He remained a practicing Catholic his whole life long and would always be modest to a fault about his musical gifts. But he was also an acutely self-aware artist with an unrelenting will, who from adolescence onward hid his vaulting ambitions behind an iron mask of affability.

One observer who saw through Crosby’s façade was the clarinetist and bandleader Artie Shaw, who watched him up close in the radio studios:

Bing was never a matinee idol. He developed a screen personality that worked because it was based on who he wanted to be—casual, relaxed. But it was a tense sort of relaxing because you knew he was working at it. Bing wasn’t Bing any more than [Humphrey] Bogart was Bogart.

For all the warmth of Crosby’s public personality, his family and friends found him distant and enigmatic. According to his younger brother Bob, a singer who fronted one of the best big bands of the swing era, he “built a cellophane bag and sealed himself inside and didn’t let anyone inside because [people] knew he was shy and that he couldn’t say no.” Apparently as a way of coping with his anxieties, he went on periodic alcoholic binges, a habit that would soon put his reputation—as well as his voice—at risk, though he finally brought it under control.



Crosby’s academic education came to an abrupt halt when he fell in love with popular music. Though his only training was a handful of singing lessons he had taken as a teenager, he had great natural ability and a quick and retentive musical memory, making it possible for him to learn new songs easily even though he could not read music. His rise to stardom was astonishingly fast: he quit school in 1924 to sing professionally, and within two years he had joined the Paul White-man Orchestra, the first full-time singer ever to be hired by a major dance band.

Contrary to widespread critical belief, the Whiteman band was one of the most musically advanced ensembles of the 20’s. In it, Crosby worked side by side with such innovative artists as the cornetist Bix Beiderbecke, the bassist Steve Brown, the guitarist Eddie Lang, and the arranger Bill Challis. He also began to listen closely to the playing and singing of Louis Armstrong, the most important figure in early jazz, whose rhythmic forcefulness and flexibility were then having an incalculably large impact on other young jazz musicians (and who in turn would later emulate Crosby’s distinctive ballad style).

While Crosby’s singing reflected all these influences, the overall effect was wholly individual: nobody sounded quite like him. It helped that the voice itself was inimitable, a resonant, virile-sounding baritone with a range of nearly two octaves, from low G to high F, and a warm, attractively husky timbre that Armstrong likened to “gold being poured out of a cup.”3

But it was what Crosby did with his voice that made him stand out. Prior to the 20’s, American popular singing was theatrical in style: singers had to make themselves heard over pit orchestras without benefit of amplification, a circumstance that forced them to employ vocal techniques not unlike those of opera singers. As it happens, Crosby’s voice was naturally large enough to have permitted him to sing that way: Kitty Carlisle, an actress with classical vocal training, heard him in person for the first time in 1934 and was startled by “his technique, his effortlessness, the fact that his voice was so much bigger and more available for, really, operatic roles than [what] you saw at the movies.”

Instead, he chose another path. With the coming of electrical recording in 1925, small-voiced, effete-sounding tenors had briefly become fashionable. But Crosby swept them away with a style that was forthrightly masculine yet intimate in scale. Thanks to his canny use of the microphone, he could sing as if he were speaking—and not to a large audience, either, but to just one person at a time.



Musically, Crosby combined Armstrong’s infallible swing with Beider-becke’s lyricism. Such early 78 sides as “I’m Coming, Virginia” (1927), “Ol’ Man River” (1928), and “Make Believe” (1928) show him to have been astonishingly light on his rhythmic feet, more so than any singer of the period besides Armstrong. He reworked melodies with the self-assurance of a master improviser, adding ornaments and altering rhythms as his fancy dictated, and his “scat” singing (the made-up nonsense syllables popularized by Armstrong), heard to especially good advantage on the electrifying version of “St. Louis Blues” he recorded with Duke Ellington’s band in 1932, was wonderfully bold.

The young Bing Crosby was, in short, a jazz singer, arguably the first one after Louis Armstrong, and without question one of the best who ever lived. He was also, as Giddins correctly points out, “the first great ballad singer in jazz. . . . His sound had little precedent: rich, strong, masculine, and clean.”

By 1931, Crosby had left the Whiteman band and the Rhythm Boys, the vocal trio with which he had been featured during his years with Whiteman, and embarked on a solo career. In that year he began to appear in short subjects directed by Mack Sennett, the king of movie slapstick, thereby revealing himself to be a natural comedian, and was hired by CBS to star in his own radio show, Fifteen Minutes with Bing Crosby.

Crosby’s movies and radio appearances advertised his recordings, which began to sell in vast quantities, and within two years he was so successful that he was able to stop performing in public altogether. Between 1933 and 1975, the only crowds he sang for were the studio audiences invited to watch his radio shows. Dozens of other pop singers based their styles on his, among them Russ Columbo, Perry Como, Bob Eberle, Billy Eckstine, Dick Haymes, and Dean Martin. “All the singers tried to be Crosbys,” one of them wryly admitted. “You were either a high Crosby or a low Crosby.” At the age of thirty, Bing Crosby had become (in Duke Ellington’s words) “the biggest thing, ever.”



But the ultimate basis for Crosby’s superstardom—his voice—was proving to be perilously fragile. He had long had problems with laryngitis (an attack of which forced him to postpone his highly publicized network radio debut for two days), and many of the records he was making in the late 20’s and early 30’s reveal a hoarseness in the upper register which, though part of his appeal, was also an unmistakable sign of strain.

Late in 1931, a doctor warned Crosby that he had developed a node (a hard blister) on one of his vocal cords, thus rendering him particularly susceptible to laryngitis. Surgery was impossible: it might alter the quality of his voice unpredictably and permanently. The only treatment was complete vocal rest, but, Crosby having just reached the peak of his early stardom, that, too, was out of the question. He kept on singing—and drinking to excess, thereby doing further damage.

According to Giddins, Crosby’s difficulties cured themselves over time. But to listeners familiar with the long-term consequences of faulty vocal technique, his records tell a different story. Though his natural tessitura was that of a low baritone, he had an upper extension that he used freely in the late 20’s and early 30’s, casually tossing off high E’s and F’s. But because he had no formal training, he never learned how to negotiate safely the “break” leading to his upper register, and a combination of overwork, drink, and flawed technique gradually weakened that part of his voice.

Crosby’s 1931 recording of Hoagy Carmichael’s “Stardust” provides a dramatic illustration of the risks he was taking. It is one of his most famous recordings, and deservedly so: his youthful ballad style, vibrant and robust, is heard here in all its golden glory. But he is also audibly hoarse, and he sings the repeated high E’s of the chorus in a wide-open, “uncovered” voice that any competent teacher would immediately have spotted as a recipe for disaster.

Predictably, Crosby had another vocal crisis in 1932, and was told to “rest and don’t even answer the phone—don’t talk, don’t do anything.” Instead, he took a ten-day break, then resumed his busy schedule. Giddins mentions this episode in passing, apparently not realizing that it marked a turning point in the singer’s career, the moment when he began irreversibly to “lose his top.” Though he continued to sing full-voiced high F’s on record as late as 1935, they became fewer and farther between, and songs that he might once have performed in the key of F, such as “June in January” and “With Every Breath I Take” (both 1934), were transposed down a full step, to E flat. Nor was the change limited to his upper register: by 1935, his voice had grown darker in timbre and heavier in texture from top to bottom.

As Crosby lost his high notes and settled into a less demanding bass-baritone range, he also changed his style. Not only did he abandon the jazzy scat singing of his young years, he seemed almost to lose interest in jazz itself. Though he was always capable of unlimbering for such frisky novelties as Johnny Mercer’s “I’m an Old Cowhand” (1936) and “Bob White (Whatcha Gonna Swing Tonight?)” (1937, with Connie Boswell), he now concentrated on ballads, which he sang with a quiet warmth well suited to his deeper range.

By this time, Crosby was recording for Decca, a new label whose chief producer, Jack Kapp, had encouraged him to explore a repertoire better suited to the tastes of “the masses.” Kapp assured Crosby that by shunning “ ‘hot’ songs” and concentrating instead on a wide-ranging mixture of contemporary ballads, prewar standards (like “I Love You Truly” and “Let Me Call You Sweetheart”), collaborations with other popular Decca artists like the Andrews Sisters, and ethnic novelties ranging from country to Hawaiian music, he could attain a degree of popularity “as great as ever enjoyed by any singer in this country. You have in your grasp,” Kapp added, invoking the name of the astonishingly successful Irish tenor, “the opportunity to be the John McCormack of this generation.”

Crosby unhesitatingly took Kapp’s advice, and the results were just as predicted. By the 40’s, he was more than a pop singer, more than a movie star. Instead, he became, as Giddins rightly says, a member of the family: “No other pop icon has ever been so thoroughly, lovingly liked—liked and trusted. . . . His was the voice of the nation, the cannily informal personification of hometown decency—friendly, unassuming, melodious, irrefutably American.”



But Crosby paid a high price for allowing Jack Kapp to turn him into the musical equivalent of a Norman Rockwell Saturday Evening Post cover. Jazz is not an absolute value, and the fact that Crosby’s new style was less explicitly “jazzy” did not necessarily make it less good. (Nat “King” Cole, for example, became a better singer when he gave up jazz piano to concentrate on ballads.) The problem with the new Crosby was that his singing had become less vital, less compelling, less interesting. It was as though the loss of his high notes had also robbed him of his sense of musical adventure, his ability to surprise and delight the ear. The decline was not inexorable, and he would continue to make occasional memorable recordings well into the 1940’s. For the most part, though, he was now singing—figuratively as well as literally—in a lower key.

Gary Giddins has mixed feelings about Crosby’s change of style. “What his singing forfeited in muscularity,” Giddins argues, “it gained in poignancy. . . . Bing in the mid-30’s was the most quietly assured male pop singer alive.” Yet he also admits that there was more to it than that:

[I]n singling out McCormack as a career template and encouraging Bing to deflect hot songs, [Kapp] hoped to remake him as a smoother, less mannered, ultimately less expressive singer, a kind of musical comfort food. . . . [Crosby] was now on the verge of reinventing common-denominator aesthetics, creating a national popular music that pleased everyone. The cost, in the opinion of many observers, was encroaching blandness.

The strengths and weaknesses of the new Crosby can be heard in the great ballads he recorded during World War II “What’s New?” (Johnny Burke and Bob Haggart, 1939), “Skylark” (Johnny Mercer and Hoagy Carmichael, 1942), “It Could Happen to You” (Burke and Jimmy Van Heusen, 1943), “Long Ago and Far Away” (Ira Gershwin and Jerome Kern, 1944), and “Out of This World” (Cole Porter, 1944) rank high among the outstanding love songs of the decade, and Crosby sang them all with taste and sensitivity. But his interpretations seem almost detached, lacking the energy and ardor one might reasonably expect from a comparatively young man. To hear them is to be put in mind of Father O’Malley, the amiable priest Crosby played in the 1944 movie Going My Way. Like the good father himself, Bing Crosby in the 40’s sounded pleasant, engaging, humorous—and celibate.

By the 50’s, a new generation of Americans was transferring its musical loyalties to a very different kind of singer. Frank Sinatra started out as a “high Crosby,” but quickly developed into something more: singing with the big band of Tommy Dorsey, he brought to the ballads of the 40’s a vulnerability that teenagers found irresistible. Like Crosby, he weathered a vocal crisis from which he emerged with a lower, darker voice, but it made him more rather than less interesting. The Sinatra of the 50’s sang with a sharp edge of sexuality and aggression, while his youthful vulnerability deepened into a quality bordering at times on outright despair.

Sinatra’s emotional candor stands in stark contrast to the impenetrable reserve of Crosby, who once famously told the lyricist Johnny Burke not to write songs for him that contained the phrase, “I love you.” Unlike Sinatra, he was never a confessional artist, and the intensity he brought to his early recordings of ballads like “Stardust” was musical rather than dramatic. (To put it another way, he sang songs, not monologues.) Revealingly, he preferred the middle-of-the-road backing of John Scott Trotter’s studio orchestras to the harder-swinging, harmonically sophisticated arrangements that Nelson Riddle created for such classic Sinatra albums of the 50’s as Songs for Swingin’ Lovers and Only the Lonely.

The 50’s continue to be portrayed in the media as a decade of mindless conformity, but they were actually a time of considerable cultural volatility, nowhere more so than in popular music and jazz. While the comforting sound of Bing Crosby’s balladry remained reassuring to many Americans, others were looking for something more emotionally challenging, and Sinatra’s confessionalism, like the deceptively “cool” jazz of the trumpeter Miles Davis, suited their mood perfectly.



To the end of his life, Crosby continued to make records and appear on radio and TV, and he never lost his ability to swing. (“Bing had the beat, the absolute best time,” said the drummer Jake Hanna. “You just followed him and he carried you right along.”) But his way of making music had become unfashionable, and because the middle-aged Crosby was the only one whom younger listeners knew, they came to see him as a symbol of everything they held in contempt. As Giddins puts it:

He was known to [the postwar generation] as a faded and not especially compelling celebrity, a square old man who made orange-juice commercials and appeared with his much younger family on Christmas telecasts that the baby boomers never watched. . . . They would have been amazed to learn how advanced, savvy, and forceful a musician he had been in his prime.

Fortunately, the other Bing Crosby—the greater Crosby—lives again in the first half of A Pocketful of Dreams, and on the best of the hundreds of records he made between 1927 and 1936. “As far as I am concerned,” Crosby said in 1960, “with the exception of a phonograph record or two, I don’t think I have done anything that’s really outstanding or great or marvelous or anything that deserves any superlatives.” In fact, he was a nonpareil jazz singer who has been unfairly written out of the history of the music he helped to shape, as well as a balladeer of magical sensitivity and irresistible vitality. In helping to restore him to life, and despite certain deficiencies in musical understanding, Gary Giddins has done an inestimable service to American music.



1 Little, Brown, 728 pp., $30.00. The volume’s subtitle is “The Early Years, 1903-1940.”

2 Bing: His Legendary Years, 1931 to 1957 (MCA MCAD4-10887).

3 The mutual admiration of the two men, who worked together frequently in radio and motion pictures, was both genuine and endearing. Crosby called Armstrong “the beginning and the end of music in America,” while Armstrong’s praise for Crosby was no less emphatic: “The man was a Natural Genius the day he was born. Ever since Bing first opened his mouth, he was the Boss of All Singers and Still is.”


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