Dizzy Gillespie he dreamed of becoming a jazz musician. 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 later Teddy Hill, replacing Frankie Newton as second trumpet in May 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
Dizzy Gillespie a session led by Coleman Hawkins with Gillespie as a featured sideman on February 16, 1944 (Apollo), the first formal recording of bebop. He appeared in recordings by the Billy Eckstine band and started recording prolifically as a leader and sideman in early 1945. He was not content to let bebop sit in a niche of small groups in small clubs. A concert by one of his small groups in New York's Town Hall on June 22, 1945 presented bebop to a broad audience; recordings of it were released in 2005. He started to organize big bands in late 1945.