In the early days of the swing era, the singer Ina Ray Hutton, a vivacious performer with pinup-girl looks, led one of the dozen or so all-female orchestras in operation around the country. Now commonly misconstrued to have been a secondary effect of wartime conscription, like the All-American Girls Baseball League, the phenomenon of all-female swing bands actually arose several years before Pearl Harbor. In fact, many of the exclusively female groups had disbanded before the United States entered the war. The orchestras were usually packaged as sexy novelty attractions, much to the frustration of the musicians called upon to play demanding dance-band orchestrations and to improvise inventively while looking alluring in skintight gowns and cut-glass baubles. Male audiences ogled, and male critics shrugged. As the jazz writer George T. Simon scoffed in his biographical history, The Big Bands, “Only God can make a tree, and only men can play good jazz.”

Ina Ray Hutton, the older half-sister of the jazz-pop singer June Hutton, was known at the time as “the blond bombshell of swing.” With her platinum hair set in a soft wave, she leveraged her sex appeal to claim the leadership of an assemblage of first-rate dance-band musicians. The most conspicuously gifted among them was Hutton’s pianist, Ruth Lowe, an occasional composer who, like Irving Berlin, lost a spouse not long after getting married—Lowe’s groom died in surgery—and found herself, in mourning, moved to write a song. In 1939, Lowe, 24 at the time, wrote a softly aching melody and set it to a few short stanzas of generically prosaic words about loss—the end of a romance, according to one phrase in the lyric, though the general ambiguity of the words and the melancholy in the music suggested a deeper implication. Lowe passed the music on to one of her colleagues, Vida Guthrie, a woman who was serving as the musical director for Percy Faith, an orchestra leader who specialized in sweet and romantic mood music, and Guthrie made an arrangement of it for Faith to play on his CBC radio show. Talented female musicians of the big-band era, such as Lowe and Guthrie, were being hired almost exclusively to play either with other women or with men like Faith, who made music that was gentle, polite, and easy on the ears—music conceived of as effeminate. A copy of the music to “I’ll Never Smile Again” made its way to Tommy Dorsey, the “sentimental gentleman” with a soft spot for soft music.

Dorsey, a virtuoso of checkbook musicianship, had recently taken expensive steps to provide his band with both more musical vigor and more star appeal: He hired away the brilliant African American arranger Sy Oliver, who had been working for Jimmie Lunceford, the leader of one of the hardest-swinging black bands; and he bought out the contract of the boy singer for The Harry James Orchestra who was becoming a sensation with teenage fans, especially female ones: Frank Sinatra. Oliver gave Dorsey a Lindy-hop dance-floor hit with his re-arrangement of Jimmy McHugh and Dorothy Fields’s “Sunny Side of the Street,” once a staple at the Cotton Club; and Sinatra provided Dorsey with a bona fide hit record with his brooding, delicate reading of Ruth Lowe’s “I’ll Never Smile Again.”

Dorsey assigned the song to a small ensemble, a sub-group of his called The Sentimentalists, and they justified their name on the record released in 1940 by RCA Victor. Axel Stordahl, who would later become known for his grand, lush string orchestrations for Sinatra and others (including Ina Ray Hutton’s sister June, whom Stordahl would marry), crafted a pretty arrangement of the tune. Joe Bushkin, the pianist, tinkled an accompaniment on the celesta straight out of a dry-ice heaven scene in a movie like Here Comes Mr. Jordan; and The Pied Pipers, Dorsey’s in-house vocal group, crooned the melody in sugar-syrup harmony. The singers sounded like they were wearing costume gowns and wire halos. All this gave the record a gauzy, otherworldly feeling suitable to the notion of the song as a message to a loved one sent across the Great Divide. As such, “I’ll Never Smile Again” was a swing-era variation on a tradition that dated back to the turn of the twentieth century, when parlor musicians were singing and playing tunes like Charles K. Harris’s morbid novelty tune, “Hello Central, Give Me Heaven,” in which a child rings up her late mother on the phone.

On July 27, 1940, Billboard magazine, the trade journal for the music business, started publishing a weekly list of the best-selling records across the country, under the heading of “The Billboard Music Popularity Chart.” Prior to that issue, Billboard had published other music lists—one, as early as 1913, for “Popular Songs Heard in Vaudeville Theaters Last Week,” and others, after that, for “Sheet Music Best Sellers,” “Songs with the Most Radio Plugs,” and “Records Most Popular on Music Machines” (jukeboxes). The magazine had reported on record sales in articles and columns, but had not yet attempted to produce an ongoing, systematic tabulation of the sales of 78-RPM singles. (Long-playing records had not been invented, though the term “album” was beginning to be used for booklets packaging three or four 78s by theme, such as “Favorite Hawaiian Songs.”) The “Music Popularity Chart” was presented as a “trade service feature,” intended to provide market information for the benefit of wholesalers and retailers trying to decide what to stock, radio programmers trying to figure out what to play on the air, and songwriters and producers looking for cues on styles to mimic and trends to exploit. The chart in that issue in 1940 listed ten records, nearly all of them ballads, and most of them sad.