On New Year’s Eve, Dizzy Gillespie gave notice as well. Eckstine quickly replaced him in the lead trumpet chair with another bebop innovator, Fats Navarro. Over the next two years, Billy continued to hire sidemen who would go on to become leading lights of the new jazz movement, including Dexter Gordon, Gene Ammons, Howard McGhee, and Kenny Dorham. All of them would later call the Eckstine band an invaluable training ground and the first authentic bebop orchestra. But eventually all of them, including Sarah Vaughan, left to join other orchestras or to devote themselves to playing the new music full-time with smaller ensembles.
By 1946, Eckstine was ready for a change as well. When he returned to the Apollo in January 1946, hundreds of white female fans packed the theater along with his usual black followers. In another sign of Billy’s growing crossover appeal, he was named Outstanding New Male Vocalist for 1945 by Esquire magazine. White music critics who had dubbed Eckstine “the Sepia Sinatra” gave him a new nickname that made him sound less like an imitator than a competitor. By this time, Eckstine had shed the high-register, Cab Calloway sound of his early career and become known for his seductive baritone, made all the sexier by the quivering vocal technique he had learned from Sarah Vaughan. He was now known as “The Vibrato,” and his female fan club called themselves “The Vibrato’s Vibrators.” And before the year was over, Billy Eckstine signed his biggest record deal yet, with a label that had dreams of making “The Vibrato” from Pittsburgh as big a star as “The Voice” from Hoboken, New Jersey.
• • •
“JELLY, JELLY” MAY HAVE been Billy Eckstine’s bread and butter, but he privately resented singing the blues. It wasn’t that he disliked the music: what bothered him was that white people thought that blacks could only sing the blues. In the 1930s, when Eckstine joined the Earl Hines band in Chicago, local radio stations broadcast its performances from the Grand Terrace Café. Producers always wanted ballads to be played as instrumentals, and Hines had to insist that Billy be allowed to sing romantic songs such as “Skylark” and “You Don’t Know What Love Is.” The broadcasters made the “bullshit” argument that the radio audience couldn’t understand blacks singing slow numbers because of their Southern accents, Eckstine recalled. “Shit, man, I’m from Pittsburgh!” he would say. “What Southern accent are you talking about? The only South I know is the South Side of Pittsburgh.”
Even after Eckstine formed his own band and began recording ballads, the music industry persisted in treating him like a blues singer. In 1945, Eckstine had left Deluxe Records to sign with the National label, and his first single was a romantic tune called “A Cottage for Sale.” Billboard described it as having “a fetching blues overtone” even though, as Eckstine biographer Cary Ginell put it, “there was nothing approaching the blues about it.” When sales surpassed 150,000 records, National devoted the band’s next two studio sessions to love songs. But when “I’m in the Mood for Love” became another hit, Billboard initially insisted on listing the song on its chart of “Race” records.
By 1946, more and more white teenagers were showing up at Eckstine’s concerts, and resentment over his crossover romantic appeal bubbled up for the first time. In Boston, a drunken woman became enraged at Eckstine’s seductive crooning and rumors that his band had refused to enter the theater through the back door. She heckled him, and Billy answered back. The woman’s companion charged the stage. Patrons fled without paying, and the rest of the engagement was canceled. Shortly afterward, Eckstine received an admiring telegram from Frank Sinatra. “Congratulations, Billy,” the message said. “You have upheld the prestige and standard of the thin man’s brigade.”
While Eckstine’s band filled concert halls, however, it didn’t make money. After the cost of touring and paying sidemen, little was left. Meanwhile, white solo artists were becoming the postwar rage. For Eckstine, the point was made when Perry Como recorded a song that the Eckstine orchestra had also put out, “Prisoner of Love,” and scored Billboard’s top hit of 1946. So in early 1947, Eckstine announced that he was striking out on his own. Weeks later, he signed the most lucrative record deal ever awarded to an individual black artist. The MGM movie studio had launched a new record label, and it gave Eckstine a two-year contract that guaranteed the release of twenty-four singles, paid a $50,000 annual retainer, and offered the prospect of roles in MGM movies as well.
As it had been when he formed his own big band, one of Eckstine’s first trips as a solo performer was to his hometown. Just after signing with MGM, Eckstine received an invitation to a second annual “Night of the Stars” uniting, as the Courier described them, “native sons and daughters of Pittsburgh who have risen to the glamor-laden peak of success.” The occasion was “FROGS Week,” a treasured annual tradition named after black socialites who in the 1910s had formed an eating club they playfully dubbed “Friendly Rivalry Often Generates Success.” “Wouldn’t miss this chance to come home,” Eckstine cabled back. On a sweltering night in August 1947, he shared the stage of the Syria Mosque with a group that represented four generations of Pittsburgh musicians who had lifted each other as they climbed: Earl Hines, Billy’s former boss; Lois Deppe, the bandleader who gave Hines his start; Mary Lou Williams, who was inspired by Hines; singer Maxine Sullivan, who had joined Williams as one of the few black female musicians headlining in small New York clubs in the mid-1940s; and Erroll Garner, the East Liberty prodigy whom the Courier anointed “newest sensation among the piano gentry.” In tribute to the musical heavyweights assembled—and the role Pittsburgh had played in his own career—Joe Louis even showed up to close the evening with a mock sparring match.
With the support of MGM’s marketing muscle, recording technology and top-notch arrangers, Eckstine was on his way to becoming one of the hottest American male vocalists of the late 1940s. His first record for the new label, “This Is the Inside Story,” sold more than 100,000 copies. Three more recording sessions followed in 1947, including a marathon date that produced seven records in advance of another musicians union strike. Those songs kept Eckstine in record stores and on the radio and helped him end 1948 as Billboard’s top-ranked male singer, ahead of Bing Crosby, Frank Sinatra, and Frankie Laine.
Like his white rivals, Eckstine was becoming almost as famous for his look and his lifestyle as for his singing. Men snapped up shirts with collars in the shape of a “B.” A young Caribbean singer just out of the Navy, Harry Belafonte, grew a pencil mustache and experimented with vibrato after seeing Billy perform at New York’s Royal Roost. Tabloids oohed over Eckstine’s seven-room house in Encino and aahed over his golf outings with Joe Louis. Even scandals—such as when Eckstine and his wife, June, were each caught up in marijuana busts—didn’t halt Billy’s rise. By the end of the decade, he was so famous that he didn’t think twice about turning down the minor film roles that MGM put in front of him, believing that he was destined to play a leading man. When he was offered a part as a valet to Dan Dailey, a B-movie star, Eckstine scoffed. “I don’t carry my own fucking bags,” he said, “so why would I be carrying Dan Dailey’s?”
In 1942, bobbysoxers had mobbed the Paramount Theatre in New York City when Frank Sinatra appeared there, launching a solo career after his time as a swing band singer. Seven years later, in April 1949, Eckstine’s Paramount debut created almost as big a stir. “Billy Eckstine is doing the biggest business at the Paramount since Sinatra packed them in,” Walter Winchell reported in his syndicated column. Thousands of fans on Easter break—at least 90 percent of them white, by one estimate—descended on Times Square to see Billy perform. Shrieking women threw panties and keys onto the stage. In just two weeks, the 3,654-seat theater grossed close to $200,000, and its managers rewarded Eckstine with a $3,000 bonus and an invitation to come back during the Christmas holiday season.
By the time Eckstine returned to the Paramount for a third engagement in the spring of 1950, he was an even bigger draw. The readers of Downbeat and Metronome magazines had voted him the top male vocalist of 1949.
MGM had sold more than three million copies of his records. Membership in “Billy Eckstine Fan Clubs of America” had surpassed 100,000. Eckstine’s former moniker—“The Vibrato”—had given way to an even loftier nickname: “The Great Mr. B.”
This time, fans began lining up for tickets outside the Paramount as early at seven in the morning. At the end of his act, the theater’s hydraulic stage was supposed to lower Eckstine out of sight, but when crazed admirers tried to storm the stage the theater’s management had to nix the sinking exit.
In further evidence of his widening appeal, Life magazine commissioned a profile of Eckstine. To capture the “Billy soxers” craze, as the magazine called it, the editors assigned Martha Holmes, a twenty-six-year-old freelance photographer who had snapped one of the most memorable Life images of the previous year: of painter Jackson Pollock dripping paint on a canvas in his Long Island studio. Holmes followed Eckstine around for several days and captured the kind of candid moments that Life readers craved: Eckstine and his wife, June, dressed at their New York apartment. The singer palled around with Earl Hines and Louis Armstrong backstage. Billy arrived at the Paramount Theatre with an entourage that included Charlie Sifford, the black golf pro who moonlighted as Eckstine’s chauffeur and private swing coach.
After the Paramount run, Holmes accompanied Eckstine when he went across the street to perform at a new club called Bop City. Opened the year before, the club was designed for a new generation of jazz enthusiasts who preferred to listen rather than dance. Patrons sat at tables and drank a house specialty called the “Bop-amatic.” Further away from the stage, there was a gallery where fans could pay 90 cents to stand and watch.
As Eckstine was leaving Bop City one night, Holmes snapped a photo of a chance encounter with a group of white female fans. Billy was dressed in a light-colored plaid suit and a “Mr. B” collar shirt. His hair was neatly conked and his pencil mustache perfectly trimmed. The women looked young but sophisticated. They wore pearls and gold earrings and salon-fresh perms. Something amusing had just happened, because four of the women in the photo were convulsed in laughter. One of them, an attractive blonde, had fallen against Eckstine’s chest. Her face was pressed into his jacket and her right hand touched his lapel. Billy seemed amused, too, as he looked down at the woman with a wide smile.
Holmes later said the photograph was her favorite of the thousands she took during her long career. Its depiction of spontaneous ease among the races “told just what the world should be like,” she recalled. The Life editors liked the photo, too—but they realized how controversial an image of physical contact between a black man and white women would be. When a photo editor argued that it might be offensive to subscribers, the matter was put before Henry Luce. “Run it,” the publisher commanded.
Even then, the Life editors worried about how the image might be interpreted. When the three-page feature entitled “Mr. B” appeared in the April 24, 1950, edition, the photo took up more than half a page. Beneath it, a caption tried to make the encounter sound entirely chaste. “After a show at Bop City, Bill is rushed by admirers,” it read. “Most profess to have a maternal feeling for him. ‘He’s just like a little boy,’ they say.”
Life readers leapt to their own, far less innocent conclusions. For some black readers, it felt like a turning point in American culture. “When that photo hit, in this national publication, it was as if a barrier had been broken,” Harry Belafonte recalled. But white readers were incensed. Furious letters from two of them appeared in the magazine’s letters column three weeks later. Frank J. Roy Jr. of Columbus, Georgia, proclaimed himself “disgusted with Life for printing the picture of Billy Eckstine and his admirers.” John H. Edmonson of Fairfield, Alabama, seethed that “if that was my daughter she would be lucky to be able to sit down in a while when I finished with her.”
Decades later, the Life photograph would be widely remembered as the beginning of the end of Billy Eckstine’s rise. “It changed everything,” recalled Billy’s friend Tony Bennett in an interview with David Hajdu. “Before that he had a tremendous following, and everybody was running after him, and he was so handsome and had great style and all that. The girls would swoon all over him, and it just offended the white community.” In the view of pianist Dr. Billy Taylor, the Life photo gave white audiences a pretext to turn against Eckstine just as he was hitting the big time. “When he played the Paramount, that should have been his really big break,” Taylor said. “Many [white] people . . . were hearing him for the first time, because he had never played in white theaters . . . . The girls loved him, everything was great. But the coverage and that picture just slammed the door for him.”
In fact, the fallout from the Life photograph was more insidious. It only became apparent gradually, like a slow leak that Eckstine and his entourage couldn’t detect at first. In the months after the Life issue appeared, Eckstine continued to play premier venues from L.A.’s Shrine Auditorium to New York’s Carnegie Hall with a quintet featuring the white jazz pianist George Shearing. MGM signed him to a new million-dollar, ten-year contract that guaranteed sixteen singles and one album per year. In one of the first of those sessions, Billy recorded a ballad called “I Apologize” that became his most memorable hit. The next two years were the most lucrative of Eckstine’s career, between record royalties and nightclub fees. By 1952, he was wealthy enough to partner in a deal to buy a nightclub on Hollywood’s Sunset Strip.
Yet in retrospect, signs of a backlash were building. As Eckstine’s marriage to June Harris headed toward divorce in 1951, the press began trawling for evidence of entanglements with other women—white ones, in particular. Look magazine published a photo of Billy on a date with French movie actress Denise Darcel. Until then, he had repeatedly been rumored to be up for romantic leads in movies. Such talk abruptly stopped, just as Frank Sinatra was about to launch his show business comeback with an Oscar-winning performance in From Here to Eternity. When Eckstine was cast in an MGM musical called Skirts Ahoy!, it was only as a nightclub singer. After that, the only major part he was considered for was the role of Joe in Carmen Jones, a movie version of the all-black Broadway adaptation of the Bizet opera. Eckstine later claimed that he had rejected the role as too “Uncle Tom,” but others insisted he never had a chance once the producers fixed on a younger heartthrob, Harry Belafonte.
Despite Eckstine’s commercial success, critics started to insinuate that he himself had become a kind of musical Uncle Tom. Instead of a balladeer treated like a blues singer, he was depicted as a crass commercial crooner who had betrayed his jazz roots. Some of the griping had to do with the undeniable fact that Eckstine’s quavering baritone began to sound increasingly old-fashioned as the 1950s went on. Belafonte was popularizing the relaxed calypso sound. Sinatra was resurfacing as a swinging saloon singer. Nat King Cole had a romantic tone with more ease—and less sexual charge.
But Eckstine also couldn’t win for trying. In addition to ballads, he recorded numerous up-tempo numbers for MGM, assisted by the label’s talented young arranger Nelson Riddle. Yet it was only when Riddle went over to Capitol Records and began working with Frank Sinatra that he won widespread acclaim. When Eckstine did go back to his roots—touring with George Shearing and Count Basie, or breaking into scat singing to remind listeners that Sarah Vaughan had learned that particular technique from him—it went largely unnoticed.
In 1954, the bottom started to fall out. After Eckstine’s divorce from June Harris was finalized, he departed on a tour of Europe. Like many black musicians of the era, he found that he was appreciated even more abroad than at a home. But that welcome only increased Eckstine’s bitterness when he was forced to return to the United States to deal with financial troubles. Charging Billy with dodging taxes, the government had put a lien on his home in Encino, the beginning of decades of battles with the IRS. A nationwide tour with Peggy Lee was canceled due to lack of promoter interest. Eckstine’s ten-year deal with MGM was almost half over, and he hadn’t had
a top ten hit since “I Apologize.” In early 1955, Jet magazine, the new weekly digest of black entertainment and social news, asked on its cover “Is Billy Eckstine Through?” The story inside criticized MGM for not giving Eckstine enough support, but also quoted industry insiders confirming his slump. “Billy needs a [hit] record very, very badly,” said a Downbeat editor.
Soon afterward Eckstine announced that he was exercising a five-year exit option with MGM and signing with RCA Victor. But that move was eclipsed by much bigger news: RCA had snagged Elvis Presley. By April, Presley’s first singles for the label—“Heartbreak Hotel” and “Blue Suede Shoes”—topped the charts. Hoping to capitalize on the rock ’n’ roll craze, RCA convinced the forty-one-year-old Eckstine to record two Presley-inspired numbers: “The Tennessee Rock ’n’ Roll” and the embarrassingly titled “Condemned for Life (With a Rock and Roll Wife).” Predictably, they didn’t sell. Nor did anything else Eckstine produced in five studio sessions for RCA. At the last one, he recorded a tune that songwriter Jimmy Van Heusen had just written for an as yet unreleased movie starring Frank Sinatra. After RCA failed to do anything with Eckstine’s version of “All the Way,” it became another hit for Sinatra and Capitol Records.
In 1957, just as RCA dropped Eckstine after one year, Billy returned to Pittsburgh to bury his father, Clarence. Resigned to the end of his career as a hit-maker, Billy began to come home musically, too. He joined Count Basie, Lester Young, saxophonist Zoot Sims, and trumpeter Chet Baker for a “Birdland All-Stars” concert at Carnegie Hall. He reunited with Sarah Vaughan to record Irving Berlin tunes and a sophisticated jazz album called Billy Eckstine’s Imagination. He signed a new deal with Roulette Records, a minor label owned by the controversial musical producer Morris Levy who would later be convicted for his ties to the Mafia. Although not widely distributed, the albums Eckstine made for Roulette showed that he could still be a musical pioneer. In one, he sang French ballads orchestrated by an up-and-coming young arranger, Quincy Jones. In another, recorded at a studio in Brazil, Billy became the first American singing star to devote an album to the Bossa Nova sound.
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