Finally I got some clothes of my own.” (DeVeaux 177) One of the priorities of a jazz musician was to look sharp in order to present the image of affluence. “Pinstripes, pegged pants, drapes, beautiful stud, made me feel like a million wearing it. His first purchases upon receiving his paycheck were three suits bought on credit. Arriving in New York in 1935, he landed a job after three days that paid 8 dollars a week. Gillespie got his start in New York by way of Philadelphia. He however would drive much of his inspiration from Calloway in his usage of physical comedy and hip attitude. He felt stifled to a degree by the self-satisfied atmosphere of the band. Though Calloway’s band was considered to be the most elite group of the black music world, Gillespie nonetheless felt disillusioned.

He would eventually find employment with Cab Calloway but this position was found to be less than ideal. In addition to his technical mastery, he was able to improvise madly and soon became infamous for his ribald onstage humor. Fully committed, he steadily gained employment due to his uncanny ability to sight read and rapidly commit notes to memory. Steadfastly devoted to his music, Gillespie refused to take on a day job, considering that to be a compromise. Gillespie was always on the lookout for ways to improve his career and went about his affairs in a very detailed manner. A careful studier, he meticulously became a virtuoso at the piano and trumpet, as well as an excellent orchestral arranger. Though he would admit that his music lacked a certain ‘bluesy intensity’, Gillespie was completely self-taught in his musical ability. Offstage, he was an astute businessman and a teetotaler. Gillespie was noted for his playful performance style capped with biting humor and a playful attitude. Known as “the sound of surprise”, Gillespie was one of the foremost figures of bebop music.

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