Lena Horne and Billy Strayhorn just missed meeting in Pittsburgh. If Lena had befriended Billy’s piano teacher Charlotte Catlin earlier, or Billy had stayed longer, they surely would have encountered one another there. But in 1939, the year before Lena started performing with Catlin, Billy left for New York on an odyssey that began when he, too, started playing in the homes of white Pittsburghers.

At the end of 1938, Strayhorn was still working at the Pennfield Drug Store in Shadyside, manning the fountain and making drop-offs. Sometimes he would stay to play piano at the homes to which he delivered, and as word of his talent spread he started getting work performing at private dinners and cocktail parties. A fellow employee at the drugstore named David Pearlman heard Billy play and was so impressed that he had an idea. Pearlman was studying for a druggist license at the University of Pittsburgh School of Pharmacy, and one of his classmates was George Greenlee Jr., the nephew of Gus Greenlee. One day, Pearlman pulled George aside to sing Billy’s praises. “George, we have a delivery boy who’s one of the finest musicians I’ve ever heard,” he said. “Your uncle knows all the biggest musicians. Why don’t you introduce him to someone?”

George had never met Billy but he trusted Pearlman, who was one of the few white pharmacy students who treated him as an equal. George happened to know that his uncle was throwing a big party that night at the Crawford Grill for Duke Ellington, who was in Pittsburgh playing at the Stanley Theatre. Assuming the festivities wouldn’t start until the show was over, George waited until after midnight and headed straight to Gus’s private club on the third floor of the Crawford Grill. Sure enough, Duke was there. As soon as his uncle introduced them, George made his pitch. “A good friend of mine has written some songs,” he said, stretching the truth, “and we’d like for you to hear them.” George figured that Duke wouldn’t refuse in front of Gus, and he was right. “Well, why don’t you come backstage tomorrow after the first show?” Ellington said.

An early December snow was falling outside the Stanley Theatre when Billy met George there the next day. They took in the one o’clock matinee, then made their way to Ellington’s dressing room. They found Duke stretched out on a chair, head back and eyes closed, having his hair conked. Ellington motioned toward an upright in the corner. Show us what you can do, he said. Billy sat down to the piano.

“Mr. Ellington, this is how you played this number in the show,” Billy said, producing a note-for-note imitation of Duke’s rendition of “Sophisticated Lady” during the matinee. Then Billy said: “Now, this is the way I would play it.” His fingers returned to the keyboard, and out came an up-tempo version in a different key that was “pretty hip-sounding,” as George Greenlee remembered it.

Amazed, Duke got up and stood over Billy at the piano. “Can you do that again?” he asked. Billy played another of Ellington’s best-known songs, “Solitude,” first as Duke had performed it during the matinee, then with a different harmonization.

Ellington asked his valet to fetch Harry Carney, his baritone saxophonist. As Carney entered the room Duke whispered: “Listen to this kid play!” Carney went to alert two other stars in the orchestra, alto sax player Johnny Hodges and singer Ivie Anderson. When they got back, Duke had his hands on Billy’s shoulders and was asking him to play his own compositions. Billy obliged with “Something to Live For,” from Fantastic Rhythm. Then he played another tune he hadn’t named yet. When Duke asked what it was called, Billy laughed. Later, Ellington described it as the moment he became truly captivated with Billy Strayhorn, when he first heard the sound of Billy’s laughter.

In the few days Ellington had left in Pittsburgh, he gave Strayhorn assignments to see what more he could do. He asked Billy to write a lyric, then an original orchestration. When Billy returned with his handiwork, Duke was between shows in his dressing room, having dinner with a mocha-skinned beauty named Thelma Spangler, an aspiring musician and recent graduate of Schenley High School whom Ellington had met the night before at the Loendi Club. Billy spread his sheet music on the floor and Duke pored over it for several minutes. Then Ellington scooped up the pages and Thelma watched from backstage as he handed them out to the musicians on the bandstand, whispered a few words to Ivie Anderson, and then began conducting. An ethereal version of “Two Sleepy People” filled the Stanley Theatre. When it was over, Ellington beamed.

“ She figured out quickly that their relationship would never be romantic, but Lena knew immediately that she and Billy Strayhorn were destined to be soul mates. ”

Backstage, Ellington told Strayhorn that he wanted him to come to New York and work in his organization. He handed Billy a twenty-dollar bill for the orchestration and a slip of paper explaining how to take the subway from Pennsylvania Station to Duke’s apartment in Harlem.

Over the next few months, Billy agonized. He didn’t know if Ellington was serious. Since his childhood visits to his grandparents in North Carolina, he had rarely left Pittsburgh. He worried about leaving his mother. He didn’t have enough money to pay for a train ticket to New York City. But Lillian Strayhorn encouraged her Bill to pursue his dream, and one of his white bandmates from the Mad Hatters offered to travel with him and loan him money for the trip. First, though, Billy decided to write a song to offer Ellington when he got there. Sitting down to his used piano on Tioga Street Rear, he quickly banged out a bouncy tune based on the subway directions to Harlem that Ellington had given him.

When Strayhorn finally headed East, Ellington was on the road, and it took several days to track him down in Newark. Duke didn’t remember Billy’s name, but he said that he had been wondering how to find him. He asked Billy to return to New York with the band and offered to put him up in a $5-a-night room at the YMCA. Several days later, Strayhorn returned to Pittsburgh to collect his things and say goodbye to family and friends. One of the pals he phoned with the news was Ralph Koger, the young Courier reporter and fellow Westinghouse alumnus, who had listened to Strayhorn play the new song he wrote for Ellington. “Guess what,” he told Koger. “I’m going to work for Duke. I played that tune ‘A Train’ for him, and he liked it. I’m moving to New York!”

Soon Strayhorn was living with the Ellington family in Harlem and exploring the exciting new world of Manhattan, including the freedom it gave him to begin exploring his sexuality as a gay man. He started writing arrangements for the Ellington orchestra and played piano on several of its recordings. Then a showdown in the music industry presented Billy with an unexpected opportunity to demonstrate his songwriting talent. The American Society of Composers, Authors and Publishers, the organization that collected royalties for songwriters, was demanding more payment from radio programs. Instead of submitting, the stations decided to form a rival organization and boycott ASCAP songs and writers. To stay on the airwaves, Ellington needed to come up with an entirely new repertoire not attributed to him, since his existing songs were all part of the ASCAP empire. So Duke told his son, Mercer Ellington, and Strayhorn to get to work.

Laboring night and day in a Chicago hotel room, fueled by cigarettes and whiskey and blackberry wine, the two men turned out a dozen new songs for the orchestra to record. Strayhorn’s contributions ranged from several haunting ballads—“Chelsea Bridge,” “Passion Flower,” “A Flower Is a Lovesome Thing”—to a propulsive full-orchestra showpiece called “Rain Check.” He dusted off several of the songs he had written for Fantastic Rhythm in Pittsburgh, including “My Little Brown Book” and “Something to Live For.” And he wrote an arrangement for the song he had composed as a gift to Ellington that was so infectious that it became the orchestra’s new signature. Until then, Ellington’s theme song had been a languorous tune called “Sepia Panorama.” From then on, it would be Strayhorn’s piano-stomping, trumpets-blaring, saxes-purring orchestration of “Take the ‘A’ Train.”

The Ellington orchestra made its first recording of “Take the ‘A’ Train” in Hollywood during a West Coast swing in early 1941. While Duke was there, he was invited to a party hosted by an MGM movie writer named Sid Kuller. Ellington played the piano for the crowd, which grew so exuberant he described them as “jumping for joy.” Before the night was over, Kuller had convinced Duke to write a full-length stage show around that theme. That summer, the musical entitled Jump for Joy opened at the Mayan Theatre in Los Angeles with an all-black cast and a lineup of songs that included several more soon-to-be classics: “Rocks in My Bed,” “I’ve Got It Bad and That Ain’t Good,” and an instrumental number that would later be put to lyrics with the title “Just Squeeze Me.” Ellington was listed as the writer of all those tunes, with Billy Strayhorn credited in the program only for “musical arrangements.” But Kuller and others would confirm that Billy collaborated with Duke on almost every song in the musical, a role that would have come naturally to him after his experience in Pittsburgh writing and rehearsing the entire production of Fantastic Rhythm.

It was also during the summer of 1941 in Los Angeles that the paths of Billy Strayhorn and Lena Horne finally crossed. Fleeing Pittsburgh for New York in late 1940, Lena had found her spot in Noble Sissle’s orchestra taken. Instead she landed a job singing for a white swing band led by saxophonist Charlie Barnet that had won respect from black audiences with its jazzy recording of “Cherokee.” Through Barnet, Lena was introduced to John Hammond, the talent scout for the Greenwich Village nightclub Café Society. On its small stage, Lena was able to display the intimate singing style that she had perfected in the drawing rooms of Pittsburgh, and her performances won new friends and admirers among the sophisticated mixed-race crowd that frequented the club, from Benny Goodman and Paul Robeson to the artist Romare Bearden.

Lena moved into her grandparents’ old house in Brooklyn, and for several months Little Teddy came to visit. At Easter time, Big Teddy also arrived from Pittsburgh, and while he was in New York he once again took Lena to see Joe Louis train in New Jersey. Joe was now the heavyweight champ, and the shy chorus girl he had met five years earlier was a full-grown woman in a fox stole, silk stockings, and open-toed shoes. They began a secret affair. When light heavyweight champ Billy Conn challenged Louis for his title in May, Lena asked John Hammond to drive her around Central Park so she could listen to the fight on his car radio. Until Louis finally knocked Conn out in the thirteenth round, Lena was a nervous wreck, punching Hammond as though she was in the ring herself and leaving black-and-blue marks all over his arm.

The affair with Joe Louis didn’t last long, but it wasn’t the only dalliance Lena had during this time. Another Café Society regular was Duke Ellington, who liked to come downtown to mix with the bohemian crowd. Lena had first seen Ellington in her Cotton Club days, when he had no idea who she was, but now he laid on his regal charm and they, too, had a brief fling. It also ended quickly, but not before Duke helped convince her to pursue a new job opportunity in Los Angeles. A club owner named Felix Young was planning a big new spot called the Trocadero and wanted to hire Lena as a featured singer. She was reluctant at first, but Duke flattered her by telling that it was her duty to “let the whole world benefit from your incredible radiance.” He also said he wanted to introduce her to a friend he called “Swee Pea” who was working on a new musical they planned to debut in Los Angeles. “You’ll get to meet ’Pea because we’re getting ready to open Jump for Joy there,” Ellington said.

Shortly after Lena arrived in California, Duke sent her a ticket to one of the first performances of the show. The seat next to her was empty, but during intermission a small man sat down in it. “I’m Billy Strayhorn— Swee Pea,” he said, clasping her hand. To Lena, he looked more like an elegant owl, with his round face, thick glasses, and smartly tailored suit. But his soft voice and warm manner immediately put her at ease. After the show was over, she invited him to her apartment, and they talked through the night. She figured out quickly that their relationship would never be romantic—and she even suspected that Duke had sent him as a chaperone to keep other men away—but Lena knew immediately that she and Billy Strayhorn were destined to be soul mates.

One of the first things Billy and Lena talked about that night, Horne would tell Strayhorn’s biographer, was Pittsburgh. She didn’t go into greater detail, but it is very likely that they discovered their common bond with Charlotte Enty Catlin, Billy’s piano teacher and Lena’s accompanist. They may have marveled at the ties between Lena’s father, Teddy, and Gus Greenlee, the man who had made it possible for Billy to meet Duke Ellington. Both would later speak of the similar sense of humor and world-view they discovered that evening, and it isn’t hard to image that they found it in part by gossiping and laughing about the colorful characters and cultural quirks of black Pittsburgh.

Over the next few months, Billy and Lena became inseparable. They went to an L.A. sanatorium to visit Jimmy Blanton, Ellington’s talented young bassist, who had started his career performing on riverboats with Fate Marable and was now sick with the tuberculosis that would claim his life at age twenty-three. They frequented Alabama and Brothers, two nightclubs in the black section of town that attracted a hip mixed-race crowd. Billy also helped Lena prepare for her debut at the Trocadero, which was still under construction. He suggested songs that matched her voice, wrote flattering arrangements and coached her on her delivery, picking up where their mutual coach Charlotte Catlin had left off.

On December 7, 1941, Billy and Lena were rehearsing at the home of friends when they heard the awful news about Pearl Harbor. They gathered around a radio and listened speechlessly, sensing that the attack would change everything but not yet knowing how. For Lena, it would mean that her move to Los Angeles would turn out very differently than she had expected. As war rationing went into effect, Felix Young canceled his plans for a grand nightclub and instead opened a tiny venue he called the “Little Troc.” Instead of show-stoppers, Strayhorn helped Lena develop tunes and arrangements to fit the smaller space, songs such as “Honeysuckle Rose,” “There’ll Be Some Changes Made,” and Harold Arlen’s “Blues in the Night.” Lena’s extended run at the Little Troc would make her the toast of the Los Angeles music scene, and lead to a series of wartime film roles that turned her into one of black America’s leading movie stars.

From Smoketown: The Untold Story of the Other Great Black Renaissance by Mark Whitaker. Copyright © 2018 by Mark Whitaker. Reprinted by permission of Simon & Schuster, Inc.