Gillespie dropped out of junior high school during the Depression in order to support the family and worked like so many in the cotton fields (on WPA projects). In 1935, he moved to Philadelphia rejoining his mother. He got a job with the Frankie Fairfax band that, within a few days of his arrival, conferred Gillespie's nickname on him". The drummer, Norman Dibble, asked "Where's Dizzy?" The name stuck. Dizzy remained with the group until the spring of 1937. In 1936, the trumpeters Charlie Shavers and Carl "Bama" Warwick had joined the band. For the first time, Gillespie had the chance to discuss technique and experiment with trumpeters (of his age). He learned to imitate Louis Armstrong (and still not yet Roy Eldridge). - Gillespie told a lot of stories about his life and musical education that cannot be true. For instance, Shipton found out that it had been impossible for Gillespie to have listened to Roy Eldridge on the radio in Cheraw as a boy since Eldridge had not been broadcasted during those years. In Shipton's opinion, Gillespie had been influenced in the beginning by Louis Armstrong - Gillespie probably denied it because of Satch's manifest antipathy towards Bepop - by swing star Charlie Shavers and by Henry (Red) Allen.
With Charlie Parker, Gillespie jammed at famous jazz clubs like Minton's Playhouse and Monroe's Uptown House, where the first seeds of bebop were planted. Gillespie's compositions like "Groovin' High," "Woody n' You," "Anthropology," "Salt Peanuts," and "A Night in Tunisia" sounded radically different, harmonically and rhythmically, than the Swing music popular at the time.
After leaving Eckstine, Gillespie formed his own group for an engagement at the Onyx Club on 52nd Street. The 52nd Street clubs effectively launched a new jazz style that had previously been played privately at late night jam sessions. "The opening of the Onyx Club represented the birth of the bebop era," Gillespie wrote in his book, To Be or Not to Bop. Describing the new approach, Gillespie wrote, "We'd take the chord structures of various standard and pop tunes and create new chords, melodies, and songs from them."
Gillespie influenced many of the young musicians on 52nd Street, like Miles Davis and Max Roach, in the new style of jazz. After a lengthy gig at Billy Berg's club in Los Angeles, though, which left most of those in the audience ambivalent or hostile towards the new music, the band broke up.