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 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