Duke Ellington grew up in a middle-class family in Washington, D.C., and began studying piano at age seven. He first played in New York City in 1923 and led a sextet that grew in popularity. His band was periodically the house band at the Cotton Club in Harlem, where the band grew into a big band. He selected his musicians for their expressive individuality and included players such as Cootie Williams, Rex Stewart, Lawrence Brown, Harry Carney, Johnny Hodges, Barney Bigard and others. With these exceptional musicians, who remained with him throughout the 1930s, Ellington made hundreds of recordings, appeared in films and on radio, and toured Europe in 1933 and 1939.

Billy Strayhorn (who lived in Pittsburg, Pennsylvania) met Ellington in 1938 in Pittsburg at a performance and showed the bandleader how he would have arranged one of Ellington's pieces. Ellington was impressed and arranged for Strayhorn to meet him when the band returned to New York. Strayhorn worked for Ellington for the next twenty-five years as an arranger, composer, pianist and collaborator.

Strayhorn, from a popularity standpoint, was in Duke Ellington’s shadow. But according to Duke, Billy “was my right arm, my left arm, all the eyes in the back of my head, my brain waves in his head, and his in mine.” Billy Strayhorn wrote about 40% of Duke Ellington’s repertoire during his tenure, which lasted almost three decades. His touch left a significant mark on Ellington’s musical identity and brand. Those decades are arguably Duke Ellington’s most adventurous period.

The nature of the collaboration between the Duke and Strayhorn remained a mystery to audiences, record buyers and critics. Who composed what? This famous question has been debated over decades between critics, musicologists and fans. From hiding scores to creating elusive stories to trick journalists, both Ellington and Strayhorn kept their collaboration behind closed doors via long-distance phone calls, in recording studios, and rehearsals with the band. Strayhorn was almost always seen in the recording studio with the Duke and even playing piano on various commercial releases and radio broadcasts.

In a 1962 interview, Duke Ellington said, “Strayhorn lives the life I would love to live. You know, he is the pure artist.”