After a notorious altercation between the two men, Calloway fired Gillespie in late 1941. The incident is recounted by Gillespie, along with fellow Calloway band members Milt Hinton and Jonah Jones, in Jean Bach’s 1997 film, The Spitball Story. Calloway did not approve of Gillespie’s mischievous humor, or of his adventuresome approach to soloing; according to Jones, Calloway referred to it as ‘Chinese music’. During one performance, Calloway saw a spit-ball land on the stage, and accused Gillespie of having thrown it. Gillespie denied it, and the ensuing argument led to Calloway striking Gillespie, who then pulled out a switchblade knife and charged Calloway. The two were separated by other band members, during which scuffle Calloway was cut on the hand(?).
During his time in Calloway’s band, Gillespie started writing big band music for bandleaders like Woody Herman and Jimmy Dorsey. He then freelanced with a few bands – most notably Ella Fitzgerald’s orchestra, composed of members of the late Chick Webb’s band, in 1942.
Gillespie avoided serving in World War II. In 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 thereafter classed as 4-F. In 1943, Gillespie 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, “People 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”.
Next, Gillespie joined Billy Eckstine’s (Earl Hines’ long-time collaborator) big band and it was as a member of Eckstine’s band that he was reunited with Charlie Parker, a fellow member of Hines’s band. 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.
Bebop was known as the first modern jazz style. However, it was unpopular in the beginning and was not viewed as positively as swing music was. Bebop was seen as an outgrowth of swing, not a revolution. Swing introduced a diversity of new musicians in the bebop era like Charlie Parker, Thelonious Monk, Bud Powell, Kenny Clarke, Oscar Pettiford, and Gillespie.
Through these musicians, a new vocabulary of musical phrases was created. With Charlie Parker, Gillespie jammed at famous jazz clubs like Minton’s Playhouse and Monroe’s Uptown House. Charlie Parker’s system also held methods of adding chords to existing chord progressions and implying additional chords within the improvised lines.
Gillespie compositions like Groovin’ High, Woody ‘n’ You and Salt Peanuts sounded radically different, harmonically and rhythmically, from the swing music popular at the time. A Night in Tunisia, written in 1942, while Gillespie was playing with Earl Hines’ band, is noted for having a feature that is common in today’s music, a non-walking bass line. The song also displays Afro-Cuban rhythms. One of their first small-group performances together was only issued in 2005: a concert in New York’s Town Hall on June 22, 1945.
Gillespie taught many of the young musicians on 52nd Street, including Miles Davis and Max Roach, about the new style of jazz. It is said that when Davis asked Dizzy to teach him to play like Dizzy did, Dizzy’s reply was an acerbic, ‘learn to play your own style’. After a lengthy gig at Billy Berg’s club in Los Angeles, which left most of the audience ambivalent or hostile towards the new music, the band broke up. Unlike Parker, who was content to play in small groups and be an occasional featured soloist in big bands, Gillespie aimed to lead a big band himself; his first, unsuccessful, attempt to do this was in 1945.