After Frank Sinatra, Nat King Cole is the best remembered of the singers who dominated American popular music between the end of the big-band era and the advent of rock ’n’ roll. Chiefly known today as a performer of romantic ballads, he had a dark, grainy baritone voice with which he sang in a style at once intimate and unmannered. While Cole’s reputation went into a temporary eclipse as a result of his early death—a lifelong chain smoker, he died of lung cancer in 1965, three decades before Sinatra gave his last public performance—he was restored to prominence in 1991 when his daughter Natalie, herself a talented pop singer, released a single of “Unforgettable” in which his original performance of the song, recorded 40 years earlier, was electronically superimposed on her own to create a “virtual duet.” The record put Cole back in the limelight, and he has been there ever since.

Comparatively few of Cole’s latter-day fans, however, know that he was more than a singer. In fact, he had started out as a jazz pianist of the highest distinction, the leader of the King Cole Trio, a “cocktail combo” (as such small groups were known in the ’30s and ’40s) that featured both his singing and his playing. To this day, singer-instrumentalists such as Diana Krall and John Pizzarelli continue to model their groups on the King Cole Trio’s stylish, tightly routined records, and Cole’s own brilliant playing left its mark on any number of younger pianists, among them Ahmad Jamal, Oscar Peterson, George Shearing, and Bill Evans, who called him “probably the most underrated jazz pianist in the history of jazz.”

Had Cole continued to lead the trio, he would be generally acknowledged as one of the most important jazz pianists of the 20th century. But the ballads he sang with his trio were so enthusiastically received by the public that he started cutting vocal records accompanied by studio orchestras, and these proved even more successful than their jazz-oriented predecessors. As a result, the King Cole Trio disbanded in 1951, and it was as a pop singer, not a jazz instrumentalist, that Cole was known thereafter and to this day.

Incredibly, Cole’s singing was as extraordinary as his playing. With the sole exception of Louis Armstrong, he is the only major jazz musician to have been identically distinguished and influential as both an instrumentalist and a vocalist. Moreover, his appeal, like that of Armstrong, crossed racial lines, and did so at a time when much of America was still segregated, a fact that led to his being assaulted on stage by a group of white supremacists during a concert he was giving in Birmingham in 1956. Yet despite this and other close encounters with the evils of racism, Cole remained outwardly unfazed and his white fans staunchly loyal.

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THE STORY of Cole’s life, which is told in Will Friedwald’s Straighten Up and Fly Right (2020), the first factually reliable primary-source biography of the singer-instrumentalist, runs parallel to and sheds light on many key aspects of the black experience in 20th-century America.

The first of these is the so-called Great Migration that brought 6 million Southern blacks northward to seek better, freer lives in America’s largest cities. Among them were Nat Cole and his family. Born in Montgomery, Alabama, in 1919, Nathaniel Adams Coles (he dropped the “s” after he started playing music professionally) was one of four musically talented sons of a grocer who longed to preach the gospel. The Coles family moved to Chicago in 1923 and Edward, Nat’s father, set up shop as a Baptist minister, with Perlina, his wife, leading the choir of the True Light Baptist Church and playing organ. Perlina also gave young Nat piano lessons, and although nothing specific is known about his course of study, it is obvious from the exceptional technical finish of his jazz playing that he received thorough training in the fundamentals of classical piano.

But while Cole’s studies were central to his artistic development, he became obsessed early on with jazz in general and the pianism of Earl Hines in particular. The “trumpet-style piano” of Hines, who played on Louis Armstrong’s hugely influential 1928 recordings, combined darting, horn-like, right-hand solo lines played in octaves with angular left-hand accompanying patterns. The resulting broken rhythms disrupted the squared-off regularity of James P. Johnson, Fats Waller, and the other Harlem-based “stride” pianists of the period. Cole mastered this style as a teenager, adding to it an idiomatic feel for the blues that Hines lacked, along with a forward-looking harmonic vocabulary that prefigured bebop, the avant-garde jazz style of the ’40s. By the time he worked his way from Chicago to Los Angeles, settling there permanently in 1937, his playing was already fully formed.

Cole’s piano style would have made an impression under any circumstances, but it was the setting that he now created for himself—a drummerless trio consisting of piano, electric guitar, and bass—that showed it off most advantageously. Full-time combos of any sort were uncommon in the swing era, and the King Cole Trio would have stood out for that reason alone. In addition, the absence of a drummer gave the trio a transparent sound that made it easier for Cole and Oscar Moore, an unsung pioneer of jazz guitar, to toss musical ideas back and forth, supported only by the swinging bass lines of Wesley Prince and, later, Johnny Miller. The nimble, darting interplay heard on records such as This Side Up (1940) and What Is This Thing Called Love? (1944) has lost none of its freshness eight decades later.

Missing, however, is the element of contrast that Cole supplied when he started singing with the trio. His career as a vocalist, he told a reporter in 1945, had been an “accident,” going on to explain that “a trio is so limited by lack of instruments that I sort of had to sing to add to the group.” He stuck at first to lively, undemanding novelty songs such as “Straighten Up and Fly Right,” a Cole-written tune inspired by one of his father’s sermons. But music-industry insiders had already taken note of the King Cole Trio and its leader, and one of them, the songwriter Johnny Mercer, signed the group to a contract with Capitol, a new record label founded by Mercer himself that quickly became an industry powerhouse. In addition to being an incomparable lyricist, Mercer was also a shrewd talent scout, and he sensed that Cole’s singing was capable of appealing to white listeners as well as black ones (the trio had previously recorded for Decca’s “Sepia Series” of “race records” that were specifically marketed to urban blacks).

All that remained was for Cole to fully realize his potential as a vocalist—something that happened sooner than anyone, even Mercer, could possibly have expected.

In June 1946, the King Cole Trio cut the first record of Mel Tormé’s “The Christmas Song” (known for its first line, “Chestnuts roasting on an open fire”). Sensing its commercial possibilities, Cole rerecorded the song two months later, adding four violins and a harp, the first time he had ever sung with string accompaniment. The second version, released in November, established the song as a seasonal standard, and three days after recording it, Cole made an even more successful trio-only record of “(I Love You) For Sentimental Reasons” that shot to the No. 1 spot on of the pop charts, his most successful record yet.

Carlos Gastel, Cole’s manager, now started thinking of him not as a singer-pianist but as a “stand-up” vocalist who played piano on the side. Cole agreed, both because he was an ambitious man who hungered for wider popularity and because he felt that he had exhausted the creative and commercial possibilities of the trio, with which he had been working for nearly a decade. In his words: “You need to [change] for you—to keep growing. You also need to do it for the public.”

Cole’s second wife, Maria Ellington (no relation to Duke), felt the same way. Born into Boston’s black bourgeoisie, she was similarly determined to put an upper-middle-class veneer on her new husband, who in 1946 still spoke and sang with a noticeable touch of the Southern accent he had acquired from his parents. To that end, she persuaded him to move to Hancock Park, a wealthy, all-white Los Angeles neighborhood whose residents refused to accept the family (anonymous vandals burned a racial slur into their front lawn). Maria also encouraged him to part with his expensive sidemen and turn the group from “the King Cole Trio” into “Nat King Cole and His Trio,” assuring him that his singing was the draw.

Not until 1951 did Cole drop the trio for good, but in the ensuing years he had recorded a series of orchestra-accompanied ballads, among them “Mona Lisa,” “Nature Boy,” and “Too Young,” that made his artistic intentions clear. What he wanted (even if he never said so) was to become the first black popular singer to be accepted on even terms with his white contemporaries. Record companies had previously discouraged black male vocalists from recording anything but blues and novelties, but Cole, whose affable yet dignified stage demeanor was sufficiently unthreatening not to discomfit white audiences, had already surmounted that obstacle in the romantic ballads he recorded with the trio. Now they became the focus of his second career, and he soon became one of the preeminent pop singers of his generation, Frank Sinatra’s only male peer.

Though they recorded for the same label and worked with many of the same arrangers, the two men had little in common as singers. Unlike Sinatra, Cole was not a “confessional” performer whose interpretations reflected the dark side of his personality. Even when he sang bleak torch songs such as “The End of a Love Affair” (1962),
there was no despair in his inter-pretations. Instead, his style was quiet, understated, and arrestingly direct, as if he were sitting across from you, telling a story about a mutual friend. His otherwise smooth-textured voice had a faintly gravelly quality heightened by his chain smoking, and he sang with tuning-fork intonation and lapidary enunciation, though his drawn-out pronunciation of certain vowels, the long “i” of “I” and “my” in particular, was so idiosyncratic that Sammy Davis Jr. exaggerated it to witty effect in his uncanny impersonation of Cole (which can be viewed on YouTube).

Cole’s jazz roots never quite disappeared, especially when he recorded up-tempo tunes such as “Almost Like Being in Love” (1953) with arrangers such as Nelson Riddle and Billy May, sailing effortlessly atop the beat with the irresistible swing of the nonpareil instrumentalist he had been. (As Cole himself said when asked to compare himself to Sinatra, “the band swings Frank. I swing the band.”) But it was his recordings of ballads that made him a household name, and among the most memorable of them is the version of Ray Noble’s “The Very Thought of You” that he cut with Gordon Jenkins, another of Sinatra’s preferred arrangers, in 1958. It opens with an out-of-tempo reading of the first eight bars that is sung with hushed delicacy, after which Cole slips almost imperceptibly into a very slow but nonetheless danceable tempo. Each phrase is laid out with soft-spoken clarity and every syllable, even the second syllable in “flower,” comes through with etched but unexaggerated precision (so much so that one instantly notices his rare lapses from standard pronunciation, as when he makes “mere” and “idea” rhyme).

The success of these recordings led to Cole’s becoming a regular guest on the most widely viewed TV programs of the ’50s, including Person to Person, This Is Your Life, What’s My Line? and The Ed Sullivan Show (on which he appeared 14 times). It also inspired NBC to offer him his own weekly TV series, which debuted in 1956. But no national sponsor would advertise on a show hosted by a black man—it is no coincidence that Cole was attacked on stage in Birmingham in the same year that The Nat King Cole Show was launched—and the series was further limited by the fact that Cole, though he was a genial host, could not act, meaning that he was incapable of appearing in the comedy sketches that were staples of most other TV variety series of the period. As a result, he presented only singers, dancers, and instrumentalists, never comedians, and the show’s lack of range, combined with the absence of national sponsorship, kept it from making money. After 14 frustrating months, Cole called it quits, crisply telling a newspaper columnist that “Madison Avenue is afraid of the dark.”

The failure of The Nat King Cole Show left Cole feeling both frustrated and restless, but his options were limited. He could not act well enough to launch a secondary film career like that of Sinatra or appear in a Broadway musical, his other thwarted ambition, and the fast-growing popularity of rock ’n’ roll was making him sound old-fashioned by comparison with Elvis Presley and the other teen-oriented acts who had come to dominate America’s airwaves.

Constant touring paid the bills, and he remained one of the most sought-after acts in Las Vegas, but it galled him that he could not stay in the hotels where he performed, and though he continued to sing beautifully, he spent more and more studio time recording throwaway material such as the country-style “Ramblin’ Rose” (1962) and “Those Lazy-Hazy-Crazy Days of Summer” (1963), as well as a sour-grapes novelty called “Mr. Cole Won’t Rock and Roll” (1962) that served only to make him look even further out of touch.

When Capitol Records signed the Beatles to its roster, Cole knew that his days as a pop superstar were numbered. As if in recognition of the fact, his health began to deteriorate in the fall of 1964. He was diagnosed with terminal lung cancer, cut his last records on December 3, and died 10 weeks later at the age of 45, by all accounts a disappointed man.

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Five years after Cole’s death, Frank Sinatra announced his retirement from singing. Two years later, he resumed performing, reinvented himself as a stadium act, and returned to his place at the center of American popular culture. Might Cole have undergone a similar professional revival had he not died prematurely? To speculate about what might have been is obviously fruitless, though it is possible that he might have taken up the piano again and become the elder statesman of jazz that he had it in him to be.

What he could never have done was become a Sinatra-like cultural colossus, for he lacked Sinatra’s larger-than-life personality. Instead, he was content to be nothing more—or less—than a first-rate popular singer, and the reissue in 1991 of an 18-CD boxed set of the King Cole Trio’s recordings for Capitol triggered a revival of interest in his earlier work as a jazz pianist. Fortunately, it is not necessary to choose between the two Nat Coles: They were two different sides of a great popular artist, one who gave fully of himself in both capacities. In Will Friedwald’s well-chosen words, “he could do almost anything that any other artist could do, but no one else could do what he did.”

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