As it happened, Lena Horne was in town that week in October as well, performing at the Stanley Theatre downtown. The Loendi Club threw a reception to welcome her back, and Harris covered it for the Courier. Yet as Teenie’s photographs made clear, Billy Eckstine was as big an attraction as the guest of honor. Wherever he turned, women and men crowed around to be in his presence. When a cake was brought out, Billy helped Lena cut it and shared the first slice. And when the guests sat down to dinner, Eckstine was placed at the head table. While Lena strained to make conversation with her ex-husband, Louis Jones, Billy sat several places away, flirting with Lena’s friend and piano accompanist Charlotte Catlin as they picked at lobster tails.
Over the Thanksgiving holiday, the Eckstine band traveled to Cleveland and Youngstown, then returned to New York for Christmas. It appeared again at the Apollo and recorded a new song, “I Want to Talk About You,” that became another hit. As the New Year dawned, the band made a five-city swing through Texas before heading to its first West Coast engagement, at the Club Plantation in Los Angeles. In a Courier column, West Coast correspondent Herman Hill drew a comparison that would follow Eckstine wherever he went for the next decade. “Bandleader Billy Eckstine, currently in our midst at the Plantation, could easily be press agented into a sepia Sinatra,” Hill predicted. “He’s that handsome and his voice and personality put Frankie to shame.”
With his languid baritone and lounge singer looks, Billy Eckstine would come to be remembered as the black crooner who never quite made it into the same league as Frank Sinatra or Tony Bennett. In fact, the story was more complicated, and so was the man, in ways that had much to do with the culture of black Pittsburgh. Like so many of its notables, Eckstine had light features and a surface air of refinement. But he could also exhibit the grit of a Homestead steelworker and the rakishness of a Wylie Avenue racketeer. His education came in equal parts from the classroom—Pittsburgh’s Peabody High School, and Howard University—and from the streets. He was a traditionalist who sang corny love songs but also a modernist who mentored musical rebels.
Most of all, Eckstine was a restless musical entrepreneur who dreamed of making it big not only in black America but in the wider world of popular culture beyond. It was a drive that took him deeper into crossover territory than any Negro entertainer had gone before, right up to the hard limits to black advancement that became more and more apparent as the heady hopes for racial progress after World War II evaporated.
His name, William Clarence Eckstein, was passed down from his paternal great-grandfather, a white German immigrant. When Wilhelm Eckstein and his wife, Anna, arrived in America in the 1850s, they settled in Washington, D.C. Wilhelm took the Anglicized name of William and gave it to his son, who carried on the daring family tradition by marrying a black woman from Virginia, Nannie Cole. Their son, Clarence, moved to Pittsburgh around the turn of the century and met a Negro girl from the North Side, Charlotte Smith, known as Lottie. Like most migrants, the couple worked several jobs to make ends meet. Lottie was a dressmaker, and Clarence worked for a family of furriers, the Wolks. But it was Clarence’s other job as a chauffeur for Harry Milholland, the president of The Pittsburgh Press, that allowed the Ecksteins to purchase a small two-floor house on Bryant Street in the Highland Park neighborhood and raise three children there: two girls named Maxine and Aileen, and the baby of the family they called “Billy.”
His mother gave Billy his first taste of entertaining. When he was four, Lottie Eckstein put him in a production staged by the Dressmakers of Pittsburgh at a local high school. Wearing a sailor’s suit, Billy was supposed to carry an American flag across the stage. Halfway, he stumbled and fell. Rather than cry or retreat, he jumped back up and carried on as if nothing had happened. Then Billy displayed an early sign of another lifelong trait: instead of leaving the stage, he stood by the emcee’s side and stared wide-eyed at all the ladies in the production.
Billy made his singing debut accompanying his grandmother to church. Mary Ann Smith was an “Old Pittsburgher,” having migrated to the city from Maryland, with her husband, Robert Smith, in the decade after the Civil War. They settled on the North Side and joined the Avery Memorial Church, where Mary would worship for more than fifty years until her death at the age of eighty-two. She sang hymns in the choir, and when Billy was six or seven she began bringing him along to perform duets. Recognizing his gift, Lottie arranged for voice and piano lessons, which continued through his early teen years at Peabody High School in Highland Park.
At fifteen, Billy received his first introduction to business. Aiming to teach the “art of salesmanship” to local youth, Robert L. Vann had launched a program called “the Pittsburgh Courier Newsies Club.” Every Thursday, boys from across the city gathered in the Courier building on the Hill to collect freshly printed newspapers. They earned a commission on every copy they sold, and competed for a monthly prize for the top earner. To instill the habit of savings, Vann established a “purpose club” that encouraged the boys to put aside their commissions for use at Easter or on other special occasions. “All of the boys are of the aggressive, hustling types—anxious to do something to help themselves and their parents,” the Courier reported in a story that listed “William Eckstein Jr.” as one of thirty Newsies in the spring of 1930.
By the early 1930s, both of Billy’s older sisters had graduated from the University of Pittsburgh, an indication of how much the Ecksteins valued education. Aileen went to work for the Courier writing a radio column called “Wave Lengths.” Maxine became a schoolteacher, working in Pittsburgh and West Virginia before taking a job as a Spanish instructor at Armstrong High School in Washington, D.C. Seizing the opportunity to send their boy to Duke Ellington’s alma mater, the family dispatched Billy to live with Maxine so he could finish high school at Armstrong.
By his senior year, Billy already had the look of a budding singing idol, with his gangly frame, mocha-colored complexion, and pencil mustache. He began to sing with a bandleader named Baron Lee, then won an amateur contest at the Howard Theatre, imitating Cab Calloway’s version of “Stardust.” When Lottie arrived from Pittsburgh to help him prepare for graduation, she discovered that Billy had snuck away to New York to compete at amateur night at the Apollo Theater. He sang the Hoagy Carmichael tune again and beat out a sixteen-year-old Virginian who had just moved in with her aunt in Harlem. A year later, that girl, Ella Fitzgerald, won another Apollo amateur night contest that led to her hiring as the lead singer in Chick Webb’s orchestra.
Success didn’t come as quickly for Eckstine. After graduating from Armstrong High, he enrolled in a Virginia vocational school, and then transferred to Howard University. Although he was offered a musical scholarship, he dropped out after two semesters to sing in the pit orchestra at the Howard Theatre. He was fired ten weeks later, however, and had to return to Pittsburgh. He formed a band that took on visiting “orks,” as they were called, in cutting contests at the Savoy Ballroom and the Pythian Temple on the Hill. For the next three years, Billy bounced from city to city across the Northeast, working mostly as an emcee in small clubs.
In the summer of 1938, Eckstine moved to Chicago at the urging of a friend named Budd Johnson, who played saxophone in the orchestra led by pianist Earl Hines. Billy’s first job there was at Club DeLisa, a black nightclub on the South Side owned by three Italian former bootleggers. A year later, in the fall of 1939, Hines finally showed up to hear Eckstine sing. The bandleader was impressed with the way Billy crooned—and how he made ladies swoon. “Goddamn,” Hines said to a band member who had accompanied him. “I’m going to try to steal that boy. He will kill everybody.”
Eckstine was still under contract to the DeLisas, however. Even after Hines offered him a big raise, Billy was wary about crossing the former gangsters. When they agreed to let him go, he figured that it was only because even bigger mobsters—Al Capone and his brother Ralph—were part owners of the Grand Terrace Café, where the Hines orchestra played. “When the
DeLisa brothers didn’t want you to go,” Eckstine recalled, “they would take you downstairs and walk you into the icebox and do a number on you. Since I was spared that treatment, I knew that somebody up there with an iron fist in kidskin gloves was giving me an awful lot of help.”
Eckstine lent a needed dash of youth and energy to the Hines orchestra, which had dipped in popularity since its days as the top orchestra in Chicago. Although the man they called “Fatha” was usually the one to school younger musicians, it was Billy who taught Hines how to stand up for himself. Every year the manager of the Grand Terrace Café, a greedy Capone crony named Ed Fox, booked the orchestra on a tour of the South to make extra money. Not welcome in hotels or restaurants, the band members were forced to sleep and eat on run-down buses, or in the sooty “nigger cars” behind the engine on trains. They traveled from town to town, playing in tiny dance halls where they were often the target of ugly slurs, and sometimes of hurled bottles and cherry bombs as well.
The unfailingly polite Hines put up with it all, but not Eckstine. On his first trip south with the Hines band, he insisted on carrying a gun. From the window of the bus, he fired at squirrels and cows to make sure everyone within earshot knew he was armed. When Billy saw the sorry condition of the pianos that the Southern dance halls provided, he took it as an insult to Hines and would rip out the strings and mallets before the band left town. On the train ride back north to Chicago, the black musicians were ushered into a “nigger car,” where in addition to coal dust from the engine they had to endure the stench of garbage that whites in the dining car tossed into the compartment.
When the train pulled into Union Station, Eckstine jumped off the train and confronted one of the white passengers from the dining car. “Man, what were you throwing all that stuff in on us for?” he demanded. Then Billy belted the man in the face, grabbed him by the collar and hit him again. The white diner jumped on the tracks and crawled under the train to hide, but another band member came at him from the other side. “If you can stand up under there, you’re gonna be a bitch,” Billy shouted at the man, “because I’m gonna whip your ass across the tracks and back under again!”
Eventually Billy helped Hines get out from under the rapacious Ed Fox. Just as Eckstine was joining the band, the manager shut down the Grand Terrace Café, forcing the band to go on the road full-time. Thanks to Eckstine’s popularity, they had a successful run at the Howard Theatre in Washington and at the Roseland Ballroom in New York City. The orchestra also cut several new records for RCA Victor’s Bluebird label, producing Eckstine’s first hit, a ballad called “Ann, Wonderful One.” Buoyed by the success, Hines worked up the nerve to dispute his onerous deal with Fox, which committed him to working for the manager’s children even if Fox passed away. But when Hines appealed his contract to the musicians union, Fox canceled all of his engagements, forcing the orchestra to disband as the legal battle played out.
Worried that he would never perform again, Hines crawled into a whiskey bottle for a month. But then the musicians union ruled in his favor, and Eckstine encouraged him to fire Fox and sign with the William Morris Agency. By the end of 1940, the new agents had the Hines orchestra on the road again, on a tour that avoided the Deep South. Instead they traveled across Texas, then up and down California, ending in Los Angeles for a recording session that changed the trajectory of Eckstine’s career.
The session took place at a Hollywood recording studio booked by Bluebird Records. After the band had played all the songs they had prepared, they still had an hour of studio time left. “Why don’t you play some kind of blues?” a Bluebird representative suggested. While Hines and Budd Johnson worked up a melody, Eckstine stepped into another room to write the words. Twelve minutes later, he returned with a lyric inspired by a telephone conversation that he had overhead from a homesick band member. “Hello, baby, I had to call you on the phone,” it began, “ ’Cause I feel so lonesome and Daddy wants his baby home.” Then, after a middle chorus, it ended suggestively: “Jelly, jelly, jelly. Jelly stays on my mind. Jelly roll killed my pappy; it run my mammy stone blind.” Hines set up the vocal with a simple twelve-bar piano lead-in. Then, as soon as Eckstine finished signing, the trumpet section erupted with a series of forceful blasts and the clarinet played a screeching line above them. For any record buyers who didn’t know what the word “jelly” was slang for, the orgasmic finale left no doubt.
That fall, the Courier broke the news that Earl Hines had signed a deal to spend the Christmas holidays performing in the Pittsburgh area. Billing it as a “triumphant homecoming” for both Hines and Eckstine, the paper reported that the band’s hit single “Ann, Wonderful One” would be the “theme” of the tour. To build excitement, the promoter announced that the woman for whom the song was written was also coming to Pittsburgh. She was a former Cotton Club showgirl named Anna Jones who had caught Hines’s eye. Sure enough, Jones was in the audience on New Year’s Eve at the Duquesne Gardens, where seventeen thousand fans joined Eckstine in “Auld Lang Syne.”
By the time the band reached New York ten days later to perform at the Apollo, however, “Ann, Wonderful One” was forgotten. Bluebird had just released “Jelly, Jelly,” and it was an instant craze. As Eckstine drove through the streets of Harlem, he heard record stores playing the song to lure customers off the street. On opening night at the Apollo, so many people lined up for tickets that police had to keep order on horseback. Inside, as soon as Billy uttered the first words—“Hello, baby, I had to call you on the phone”—women in the audience shrieked. A man in the balcony grew so excited that he tipped over the banister and plummeted into the orchestra section.
For the rest of 1941, the Hines band rode the success of “Jelly, Jelly” on dates across America. In early 1942, it recorded two more Eckstine hits: “Stardust” and “Stormy Monday Blues.” Yet by then, America had entered the war and Hines was faced with replacing band members, such as Budd Johnson, who had enlisted in the Army. When he asked Eckstine and his drummer, Shadow Wilson, to act as talent scouts, they went after two up-and-coming musicians who had just left other bands.
One was Dizzy Gillespie, who had split with Cab Calloway after several contentious years. Eckstine had first met Gillespie several years earlier, when he moved into a building on Seventh Avenue in Harlem. Dizzy lived a floor above, in an apartment with an upright piano. Although Eckstine enjoyed listening to Gillespie practice his trumpet, he was even more impressed with how Dizzy spent hours working out his ideas on the keyboard. “Even then, you could see that Diz had his head on straight, man, he was completely into studying,” Eckstine recalled.
The other sideman was Charlie Parker, the dazzlingly inventive saxophonist known to his fellow musicians as “Yardbird.” Eckstine knew Parker was available because the saxophonist had approached Earl Hines one night in Harlem and asked for a job. Parker was so desperate to leave Jay McShann, the bandleader who had brought him to New York from Kansas City, that he offered to give up his alto saxophone and play tenor instead, as long as Hines bought him a new instrument.
Eckstine and Wilson tracked Dizzy Gillespie down at a club in Philadelphia where he was playing temporarily. As Gillespie later described it: “These greasy muthafuckas cruised me out of Philly to go with Earl Hines. They told Yardbird, ‘Well, Diz is coming over here.’ Then to me they said, ‘Well, you know we’re getting Yard.’ And then Billy Eckstine and Shadow got Earl Hines to offer me $20 a night to go on the road. So I took it. They got Charlie Parker the same time—cruised him in there.”
• • •
DIZZY GILLESPIE WAS FIFTEEN years old when he began trying to imitate Roy Eldridge. Dizzy had been playing the trumpet for three years in his hometown of Cheraw, South Carolina, and he liked to listen to the broadcast of the Teddy Hill Orchestra performing at the Savoy Ballroom that aired every weekend on NBC radio. At first Dizzy didn’t know the name of the band’s trumpet soloist, he recalled, but he knew his sound “knocked me out.” Dizzy began trying to
reproduce the trumpeter’s scratchy timbre, his flashy runs of eighth and sixteenth notes, and his use of the high register. At night, he even dreamed that they were playing together on Teddy Hill’s bandstand.
Dizzy didn’t know it yet, but his infatuation with the best trumpet player to ever come out of Pittsburgh was putting him on a path to the invention of bebop.
Born on the North Side, Roy Eldridge was introduced to music by his mother, Blanche, a gifted pianist who could play almost anything by ear. By age six, Roy was banging out blues phrases on the keyboard and taking lessons on the drums so that he could play in a fife and drum corps that marched through his North Side neighborhood on holidays. Short, restless, and fiercely competitive, Eldridge burned to outdo his older brother, Joe, who played everything from the clarinet and the saxophone to the violin. It was Joe who, after hearing his younger brother play bugle in church, urged him to take up the valve trumpet. Roy began studying with P. M. Williams, a local barber and amateur musician who taught him how to breathe and hit high notes by squeezing his diaphragm. In his early teens, Roy’s mother passed away and his father remarried, and Eldridge escaped the family drama by locking himself in his room and practicing the horn.
In ninth grade, Eldridge’s hot temper and disdain for any study other than music got him expelled from high school. He ran away from home, joining a tent show that traveled across Ohio. At some point, he got his hands on a 78 rpm record of Fletcher Henderson’s band playing a lively rag called “The Stampede.” Instead of trying to copy the regal, fluid playing of the band’s trumpeter, Louis Armstrong, Roy practiced reproducing the more frenetic, raspy solo of saxophonist Coleman Hawkins.
By the time Eldridge returned to Pittsburgh at age seventeen, he had developed a unique sound and a growing reputation as the king of dance hall “cutting contests.” He briefly changed his stage name to Roy Elliott to organize a band called the “Palais-Royal Orchestra,” then he teamed up with his brother Joe to form “The Twelve Rhythm Kings.” When Eldridge moved to New York in 1935, fellow musicians astonished by how such a small man could produce such a big sound nicknamed him “Little Jazz.” Soon Roy joined the bandstand of the Teddy Hill Orchestra, one of the most coveted seats in the city because of the national exposure it got through the NBC radio broadcasts.
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