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.

At the bottom of the list, at No. 10, was “Make Believe Island,” a limpid quasi-tropical ballad recorded by a group named in recognition of the voguishness in popular music and the importance of the female audience: Mitchell Ayres and His Fashions in Music. Listed above “Make Believe Island” were songs nearly all striking for their musical languidness and lyrical melancholy: “Sierra Sue,” a pokey, vaguely Western ballad with Bing Crosby whispering about being “sad and lonely” over wistful strings; “The Breeze and I,” a semi-exotic English-language adaptation of the Spanish ballad “Andalucia,” in which both the singer and the air currents “sigh that you no longer care”—a lament of self-pity with echoes of “After the Ball,” performed by Jimmy Dorsey; and two versions of Jimmy Van Heusen and Johnny Burke’s “Imagination,” by both Tommy Dorsey and Glenn Miller. At No. 1 was “I’ll Never Smile Again,” recorded by Tommy Dorsey and His Orchestra, with a vocal refrain by Frank Sinatra and The Pied Pipers.

When we think of the pop charts, we tend to conceive of hit songs as bouncy and cheery puff. We imagine hits as having a self-defining airiness, a lightness of spirit which critics of pop sometimes project upon the music’s audience and conflate with dimness of mind. Hit songs, as we generally think of them, are resolutely, simplistically upbeat expressions of romantic bliss—and so a great many hits have been. Long before Paul McCartney and Wings, there were deeply silly love songs such as “You Are My Sunshine,” which was published the same year that “I’ll Never Smile Again” became a hit. Yet, the musical and lyrical sunniness of “You Are My Sunshine” has never been a requisite of success for a pop tune, and love songs have always been more likely to deal with the yearning for love, the complications of love, love’s betrayal, or the loss of love (or even, sometimes, the loss of life) than the fancied bliss of love fulfilled. As the songs on the first Billboard chart remind us, a strain of sadness has long been laced through the popular songbook. Music listeners’ likes have never been restricted to things that make them happy.

The Billboard record chart purported to assess “popularity” through the measurement of sales. The underlying principle was taken as a given; that the purchase of a record was an exercise of aesthetic will, a statement of personal taste: I like that song, and here’s the proof—I paid money for it. On the radio, meanwhile, the “Your” in Your Hit Parade served to reinforce the proposition that buying a record was an assertion of individual judgment—a democratic act. That is to say, it was disk purchasers who made songs into hits; the privilege of hitmaking was theirs. The charts just documented the results.

Yet, the acquisition of anything is never purely a matter of personal will. Nor, for that matter, is the sheer desire for ownership. The urges to buy, to have, to use, or otherwise to be connected to goods—cultural products, among them—are informed by innumerable factors, including marketing and social forces. Tastes and judgments are never formed independently, in a cultural vacuum. As every citizen of the twenty-first century understands from the pervasive use of social media, and as social scientists were just figuring out in the mid-twentieth century, people’s “likes” emerge in the context of what they believe other people to favor. Personal tastes are socialized tastes, and the first Billboard chart measured the popularity of songs at the same time it helped enhance and enforce that popularity by formalizing it and institutionalizing it through a process that qualified as quantification.

Students of the mind in the twenty-first century would categorize phenomena such as the charts as social proof—testimony of popular opinion that acts to expand the popularity of that opinion. In 1940, the era of phenomenological road-travel metaphors such as the hit parade, the idea would have been referred to as jumping on the bandwagon, and the first Billboard record chart demonstrated it well. After the rendition of “I’ll Smile Again” by Dorsey and Sinatra became known as a No. 1 hit, more than a dozen other musical acts, popular or hoping to be, recorded the song. The rush to capitalize on the success of the record was such that less than two weeks after the publication date of the Billboard chart, the music writer Bill Gottlieb would report, in his nationally syndicated newspaper column, “Russ Morgan is the latest to supply an insatiable public with ‘I’ll Never Smile Again.’” Gottlieb, a good writer, generally, had momentarily forgotten that the public’s appetite for any song will inevitably be sated, only to be supplanted with a hunger for a new tune.

Donald Clarke, in his judicious study of Sinatra and his work, All or Nothing At All: A Life of Sinatra, quoted his mother on the omnipresence of “I’ll Never Smile Again” on the radio: “It was all you heard,” she said. I relay the quote in part to show how the song was perceived by the public of its day, and in part to show that I am not the only writer on music who quotes his mother in a book.

As “I’ll Never Smile Again” subsided in popularity, it became, as all major hits would become, an instrument for the measurement of the success of other songs. Gottlieb, by November 1940, described a new hit, the boogie-woogie tune “Beat Me, Daddy,” by Will Bradley and His Orchestra, as “the biggest thing since ‘I’ll Never Smile Again.’”

The pop charts elevated their own status, as well as the status they conferred upon songs and song-makers, and prompted the making of more charts—more accurate charts, more extensive charts, more specialized charts, and more, more, more charts. By the late 1950s, Billboard had devised a formula for factoring information about radio play into its song rankings, a refinement that only reinforced the circularity of the charts. The chart position of a song helped determine how much a song was played on the radio, and airplay helped determine the chart position. The system seemed inscrutably hermetic, while it was also highly susceptible to corruption. Record executives knew how to rig the charts and “buy position” by influencing deejays and retailers, as well as the magazine itself, through the weight of advertising dollars.

With the widespread adoption of bar codes and scanning during the 1980s came a way to document purchases accurately, at the retail level; and, in 1991, Billboard replaced its system of surveys, divining rods, and arm-twisting machinery with a less corruptible electronic system, SoundScan. This briefly rattled the record industry, by revealing that more people were buying country music than the old charts had suggested, and that fewer people were buying records by the big-hair guitar-rock acts that male record executives liked to be associated with, and that male store clerks liked to say that they were selling.

As evidence of the popularity of songs, sales statistics are inherently limited, of course. Commercial transactions tell only part of the story of a song’s popularity. All that occurs after the purchase (or, for that matter, what does not happen) may be as telling as the fact of the sale. I mean: A record has been sold—then, what? How often is the song played? When and why and where? Is it played for comfort, by one listener alone in a room, or for dancing at a Friday night party? What thoughts, if any, does the record provoke? What feelings does it stir—or relieve? How do other people in the record buyer’s house feel about the song? How long has the record remained in active use? Has it been traded for another record or passed down to a younger brother?

When I was a kid, one of my favorite records was “Cool Jerk,” a boogaloo single from 1966 by a one-hit group called The Capitols. (Years later, I heard that the indelible groove track might have been recorded clandestinely by the Motown house band, The Funk Brothers.) My late sister Barbara, who was six years older than me, had borrowed the record from one of our cousins, and I snatched it out of her room. A few years after that, when I was in high school, I dubbed the song onto an audio cassette mix by placing my shoebox Radio Shack cassette recorder next to my stereo speakers. That mix tape became the primary source of music in my car, a profoundly used 1968 Chevrolet that seated seven comfortably, 13 for short hauls. Without aggrandizing my teen years, which were eventful only by the standards of a teenager, I can say that “Cool Jerk” was part of the soundtrack of multiple occasions memorable to my high-school friends and me. How could I capture the place that the song held in our lives? Certainly not by recounting the fact of the sale of one copy of the record to the cousin of mine who loaned it to my sister before I stole it from her. When I think of the song, I hear the jiggy-jaggy opening piano figure, and my memory drifts. I don’t hear cha-ching.

“Cool Jerk” never made it to No. 1. It peaked at No. 2 on the Billboard R&B chart, and at No. 7 on the magazine’s “Hot 100,” in July 1966. By the ostensibly quantitative and plainly mercantile terms of the pop charts, “Cool Jerk” was never as successful as any No. 1 song, from “I’ll Never Smile Again” to “Blurred Lines,” the retro-’70s white-boy funk hit by Robin Thicke that was the biggest hit in America for twelve weeks in the summer of 2013. The numbers simply do not compare, in a realm where numbers have been established as the only terms of comparison. Once a song is ranked and assigned a numerical value, the number replaces every other value—aesthetic value, social value, personal value. Identified as No. 1, a song is one number superior to the song that’s No. 2, and 98 numbers better than the song that’s No. 99. This line of thinking has become a tautology in the age of digital aggregation and data-mining, an era that the early Billboard charts and “Your Hit Parade” foreshadowed and began to make possible.

However memorable “Cool Jerk” may be to me, the pop charts have established that it will never be as big a hit as “Blurred Lines.” Memorability and hit status are essentially different matters. A hit does not need lasting power to be a hit. Indeed, it cannot last long—not as a hit. There are only so many people available to buy a song, to share one in digital form, or to share one’s interest in one through the social media; hence, the life of any song on the pop charts is intrinsically limited, like that of one of those species of insects that exists only long enough to spawn and then die. Impermanence is a necessity of the pop-culture ecosystem. The charts mark and celebrate birth and growth—songs coming up or on the rise—as they require the decline and disappearance of others. To follow a song as it ascends the chart and inevitably falls, then, is a kind of deathwatch. It may be only fitting that the first No. 1 on the first Billboard record chart was a song inspired by a death.