In the 41 years since he dropped dead on a golf course at the age of 74, Bing Crosby has become the forgotten giant of American popular culture. Among millennials, he is barely even a name, even though he was the most successful and influential pop singer of the first half of the 20th century. Crosby recorded 396 hit singles, 41 of which topped the charts—yet only one, his 1942 “creator recording” of Irving Berlin’s “White Christmas,” the bestselling record of all time, continues to be heard regularly. He was also the most popular movie star in the world for five consecutive years between 1944 and 1948, a record topped only by Tom Cruise—yet few of the four dozen feature films in which he starred are still shown with any frequency on TV, and most of those, like Holiday Inn (1942) and High Society (1956), are mainly remembered for the presence of such co-stars as Fred Astaire and Frank Sinatra.

The jazz critic Gary Giddins sought to change this by publishing in 2001 the first installment of a multivolume primary-source biography whose purpose was to reintroduce Crosby to modern listeners and make the case for his permanent significance as an artist. Despite certain shortcomings, A Pocketful of Dreams: The Early Years, 1903–1940 was generally and, for the most part, justly praised. Had Giddins brought out a second volume with sufficient promptness, he might well have accomplished his goal. But as the years went by without a sequel, Crosby’s reputation all but vanished into the grave along with the last living veterans of World War II, among whom he was so admired that it was no exaggeration that his otherwise modest tombstone describes him as “beloved by all.”

Even so, Giddins persevered, and he has now given us Swinging on a Star: The War Years, 1940–1946, which will presumably be followed at some unknown point in the future by a third volume.1 But while A Pocketful of Dreams covered a 37-year span, Swinging on a Star devotes a like amount of space to the next six years of Crosby’s life—eventful ones, to be sure, but not so much so that it would have been impossible to tell their tale far more concisely.

The fact that Crosby had three simultaneous careers—as pop singer, movie star, and host of a weekly radio series—and an eventful private life makes his story difficult to tell in a coherent way. And while it is a tribute to Giddins’s literary skill that A Pocketful of Dreams and Swinging on a Star are consistently readable, it is no less true that he has a tendency to let the piling of fact upon fact obscure the main line of his 700-page narrative.

Still, readers who want to know as much about Crosby as Gary Giddins wishes to tell us—among whom I count myself—will find Swinging on a Star a compelling study of the middle years of a popular artist who by the end of the Second World War was so closely identified with the American national character that he seemed to embody it. 


n his youth, as Giddins explains in A Pocketful of Dreams, Bing Crosby had been a jazz singer, one of the very first—and very best. As a member of Paul Whiteman’s orchestra, with which he performed from 1926 to 1930, Crosby listened closely and comprehendingly to Bix Beiderbecke and other noted white jazzmen, and he was also profoundly influenced by Louis Armstrong, who was as important a vocalist as he was a trumpeter. Even when Crosby sang the ballads that his fans increasingly favored, his still-developing style was notable for its light-footed rhythmic swing and improvisational freedom, as can be heard on the records of Jerome Kern’s “Ol’ Man River” and “Make Believe” (both from Show Boat) that he cut with Whiteman in 1928. In addition, his microphone-amplified baritone voice was unabashedly masculine at a time when most male pop singers were, like Rudy Vallée, effete-sounding tenors.

This combination of traits electrified his listeners. By 1931, Crosby was America’s biggest singing sensation, adored by the public and admired by musicians. In that same year, CBS gave him his own radio show, and for most of the next quarter-century he would be heard weekly from coast to coast. At the same time, he began to appear in movies, revealing himself to be a natural screen presence with a flair for comedy that compensated for his undistinguished physical appearance (he had a dumpy figure and a receding hairline that forced him to wear hats or a toupee in front of the camera). He became so successful as a recording artist and a star of film and radio that in 1933 he stopped performing in front of live audiences, thereafter concentrating on his burgeoning career in the electronic media.

Throughout the ’30s, Crosby’s on-screen persona was that of a likable but unscrupulous scapegrace whose casual charm made him irresistible to women. But there had always been more to his artistry—as well as to his off-stage personality. Classically educated by Jesuits, he was intelligent, well-read, and devoutly religious, and his intense, expansive 1932 recording of E.Y. Harburg’s “Brother, Can You Spare a Dime?” is one of many performances from the ’30s that do far more than hint at the passion that underlay his deceptive nonchalance. He also had an iron will that gave him what he described in Call Me Lucky, his 1953 memoir, as “the habit of facing whatever fate set in my path, squarely, with a cold blue eye.” This coldness was invariably mentioned by those who, having met Crosby, were startled by how distant he was in person. As for his will, it was so strong, he was able to bring under unaided control the taste for liquor that had pushed him as a young man to the brink of alcoholism.

None of these qualities, however, are apparent in Crosby’s work as an actor prior to World War II, by which time he had starred in two dozen feature films, all of them fluffy comedies. And while he also became the host of NBC’s Kraft Music Hall in 1936, that hugely popular weekly radio series was a music-oriented program that is of interest today mainly because he performed many songs on the air that he did not record commercially. It was in the recording studio that he made his most persuasive claims on the attention of posterity—and that he first came into his own as a mature artist.

In 1934, Crosby signed with Decca, a new record label launched by Jack Kapp, a producer with an uncanny knack for gauging mass taste. Kapp believed that Crosby, popular as he already was, could become even more so if he downplayed the jazzy side of his singing, opting instead for a simpler, more lyrical style and embarking on what Crosby later described as a “diversified record program…that embraced every type of music.” Trusting in the sureness of Kapp’s instincts, he put his recording career in the producer’s hands. It was a decision he would never regret.2

Along with the usual film, show, and Tin Pan Alley tunes, Crosby recorded an astonishingly wide variety of other songs for Decca during the next two decades, among them “Blue Hawaii,” “Deep in the Heart of Texas,” “Pistol Packin’ Mama,” “Silent Night,” “Swing Low, Sweet Chariot,” “Too-Ra-Loo-Ra-Loo-Ral (That’s an Irish Lullaby)” and “Wait Till the Sun Shines, Nellie.” In addition to recording countless solo performances, he was teamed in the studio with a similarly wide range of partners, including Armstrong, the Andrews Sisters, Connie Boswell, Eddie Condon, Xavier Cugat, Judy Garland, Louis Jordan, Mary Martin, Johnny Mercer, and Les Paul. He became a one-man musical melting pot, one whose distinctively American combination of versatility and instant recognizability was a major source of his fame. More than any other popular artist before or since, he was all things to all men, yet he resembled no one but himself. 

While jazz would always remain part of Crosby’s singing style, his voice grew deeper in the mid-’30s (in part as a direct result of vocal strain caused by overwork earlier in the decade) as well as darker in tonal color, causing him to sound less like a teen idol of the Jazz Age and more like an adult singing for other Depression-era adults. Accordingly, he now took care to steer clear of overt emotionalism—he famously preferred not to sing songs whose lyrics contained the phrase I love you—opting instead for a quiet, contained understatement that mirrored his natural reticence.

Unusually for pop singers of the period, this combination of qualities was as attractive to men as it was to women. In Swinging on a Star, Giddins cites a passage from W.R. Burnett’s 1940 crime novel High Sierra in which Roy Earle, a hard-boiled gangster portrayed on the screen by Humphrey Bogart, explains why he favors Crosby’s “mellow baritone voice”:

He’s about the only singer I like. I hate singers. They ought to have on skirts. But not that guy. He’s got a real voice and I hear he’s right all the way.

It was for a similar reason that Crosby was welcomed so wholeheartedly by the frontline soldiers for whom he performed throughout World War II, not infrequently at real risk to his personal safety. In Giddins’s astute assessment, “Bing expressed inborn virility, secure and stoic…restraint carried more weight [with the troops] than amorous histrionics.” When those same soldiers returned home after the war, they remained loyal to the man who had done so much to assuage their longing for the world they had left behind.

While Crosby’s wartime balladry occasionally flirted with blandness, it was just as often elegant and satisfyingly unmannered. Nowhere is the appeal of his new approach displayed to more persuasive effect than on his 1944 studio recording of “Out of This World,” a Harold Arlen–Johnny Mercer ballad, which is at once strikingly unsentimental and singularly beautiful. While his rich, solid tone and chiseled diction “present” the song exactly as written, he floats each successive phrase atop the beat with a subtle rubato reminiscent of the playing of a great jazz instrumentalist like Armstrong or Lester Young. 

This style, as Kapp predicted, appealed even more powerfully to Crosby’s contemporaries than the unbuttoned singing of his youth. But it took longer, as Giddins chronicles in Swinging on a Star, for him to develop a screen persona consistent with the newfound maturity of his singing. On the eve of World War II, his most popular films were the frivolous “Road” comedies that Crosby had inaugurated with Bob Hope in 1940, for which he embodied yet another variation on the same insouciant character he had been portraying on screen since 1931.

It was not until he teamed up with the director Leo McCarey to make Going My Way (1944), in which he played a genial but serious-minded priest who rescues a foundering urban parish from bankruptcy, that he was given the opportunity to play a fully developed screen character who was as mature as Crosby himself. In the words of the film critic James Agee, Father O’Malley was “a wise young priest whose arresting resemblance to Bing Crosby never obscures his essential power.” The result was a performance which disclosed for the first time that Crosby had real acting talent, a revelation to which Hollywood paid well-deserved tribute the following year by awarding him an Oscar as the best actor of 1944.


o popular artist stays at the top of the heap forever. After the war, Crosby’s popularity finally started to fade, in large part because of the simultaneous rise of Frank Sinatra. Rock ’n’ roll finished what Sinatra began, and even though Crosby sang well all the way to the end of his life, his film career dried up in the mid-’50s and he came to be seen as a nostalgia merchant, still beloved but now irrelevant.

Unlike Sinatra, who remains an icon two decades after his death, Crosby can sound on first glance unreachably distant from us today. Not only do most listeners prefer the “confessional” approach of Sinatra to his subdued restraint, but Crosby’s records of the ’30s and ’40s often lack the immediacy and punch of Sinatra’s classic albums of the ’50s and ’60s, mainly because he (and Jack Kapp) usually favored the bland backing of radio-style studio orchestras instead of the vibrant big-band-with-strings accompaniments that were later crafted for Sinatra by Nelson Riddle.

Yet anyone prepared to listen through the old-fashioned sound of Crosby’s Decca recordings and focus on the singer himself is more than likely to be astonished by his unique blend of emotional delicacy and rhythmic poise. While many of the records themselves, like most of his films, have become period pieces, Crosby the artist remains as accessible and vital as ever, so much so as to put the attentive listener in mind of Artie Shaw’s oft-quoted 1992 remark: “The thing you have to understand about Bing Crosby is that he was the first hip white person born in the United States.” So he was—and that hipness, like Sinatra’s, remains undiminished by the passing of time.

1 Little, Brown, 736 pages

2 Most of Crosby’s biggest hits for Decca are included in Bing: His Legendary Years 1931–57 (Geffen, four CDs). A representative selection of earlier sides can be found on Bing Crosby: 1926–1932 (Timeless). His rarely reissued 1944 performance of “Out of This World,” mentioned below, can be heard on YouTube.

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