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
Rhondda Gillespie formal studies were at the Sydney Conservatorium of Music under Alexander Sverjensky (where her fellow students included Malcolm Williamson, Richard Farrell and Roger Woodward) and in Britain under Louis Kentner and Denis Matthews. Wilfred Josephs' 14 Studies for Piano, Op. 53 were written for Gillespie, Joy Blech, and Yonty Solomon. Gillespie gave the world premiere of the complete set at the Cheltenham Festival in 1967. She was the second wife of the music critic and musicologist Denby Richards. They married on 29 May 1973, but divorced in 1977. In 1976, for Joseph Horovitz's 50th birthday, Gillespie played his "Jazz Concerto"