Occupation(s) Musician & Composer
Instruments Trumpet, piano and vocals
Years active 1935–1993
Labels: Pablo, RCA Victor, Savoy, and Verve
He won a music scholarship to the Laurinburg Institute in North Carolina which he attended for two years before accompanying his family when they moved to Philadelphia.
Gillespie's first professional job was with the Frank Fairfax Orchestra in 1935, after which he joined the respective orchestras of Edgar Hayes and Teddy Hill, essentially replacing Roy Eldridge as first trumpet in 1937. Teddy Hill's band was where Gillespie made his first recording, "King Porter Stomp". In August 1937 while gigging with Hayes in Washington D.C., Gillespie met a young dancer named Lorraine Willis who worked a Baltimore–Philadelphia–New York City circuit which included the Apollo Theater. Willis was not immediately friendly but Gillespie was attracted anyway. The two finally married on May 9, 1940. They remained married until his death in 1993. 
Gillespie stayed with Teddy Hill's band for a year, then left and free-lanced with other bands. In 1939, he joined Cab Calloway's orchestra, with which he recorded one of his earliest compositions, "Pickin' the Cabbage", in 1940.
After a notorious altercation between the two men, Calloway fired Gillespie in late 1941. The incident is recounted by Gillespie and Calloway's band members Milt Hinton and Jonah Jones in Jean Bach's 1997 film, The Spitball Story. Calloway disapproved of Gillespie's mischievous humor and his adventuresome approach to soloing. According to Jones, Calloway referred to it as "Chinese music." During rehearsal, someone in the band threw a spitball. Already in a foul mood, Calloway blamed Gillespie, who refused to take the blame. Gillespie stabbed Calloway in the leg with a knife. Calloway had minor cuts on the thigh and wrist. After the two men were separated, Calloway fired Gillespie. A few days later, Gillespie tried to apologize to Calloway, but he was dismissed. Gillespie started writing big band music for Woody Herman and Jimmy Dorsey. He then freelanced with a few bands, most notably Ella Fitzgerald's orchestra, composed of members of the Chick Webb's band.
Gillespie did not serve in World War II. At his Selective Service interview, he told the local board, "in this stage of my life here in the United States whose foot has been in my ass?" He was classified 4-F.  In 1943, he joined the Earl Hines band. Composer Gunther Schuller said,
... In 1943 I heard the great Earl Hines band which had Bird in it and all those other great musicians. They were playing all the flatted fifth chords and all the modern harmonies and substitutions and Gillespie runs in the trumpet section work. Two years later I read that that was 'bop' and the beginning of modern jazz ... but the band never made recordings. 
Gillespie said of the Hines band, "[p]eople talk about the Hines band being 'the incubator of bop' and the leading exponents of that music ended up in the Hines band. But people also have the erroneous impression that the music was new. It was not. The music evolved from what went before. It was the same basic music. The difference was in how you got from here to here to here ... naturally each age has got its own shit".
Gillespie joined the big band of Hines' long-time collaborator Billy Eckstine, and it was as a member of Eckstine's band that he was reunited with Charlie Parker, a fellow member. In 1945, Gillespie left Eckstine's band because he wanted to play with a small combo. A "small combo" typically comprised no more than five musicians, playing the trumpet, saxophone, piano, bass and drums.
Whatever the origin of Gillespie's trumpet, by June 1954 he was using a professionally manufactured horn of this design, and it was to become a trademark for the rest of his life. Such trumpets were made for him by Martin (from 1954), King Musical Instruments (from 1972) and Renold Schilke (from 1982, a gift from Jon Faddis). Gillespie favored mouthpieces made by Al Cass. In December 1986 Gillespie gave the National Museum of American History his 1972 King "Silver Flair" trumpet with a Cass mouthpiece. In April 1995, Gillespie's Martin trumpet was auctioned at Christie's in New York City with instruments used by Coleman Hawkins, Jimi Hendrix, and Elvis Presley. An image of Gillespie's trumpet was selected for the cover of the auction program. The battered instrument was sold to Manhattan builder Jeffery Brown for $63,000, the proceeds benefiting jazz musicians with cancer.
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