Dizzy was legendary for his ability on the trumpet, playing faster and higher than just about anybody with his trademark "balloon cheeks" and his playful stage presence.

On January 6, 1953, Gillespie threw a party for his wife Lorraine at Snookie's, a club in Manhattan, where his trumpet's bell got bent upward in an accident. He liked the sound so much he had a special trumpet made with a 45 degree raised bell, which became his trademark.

In the 1940s Gillespie, along with Charlie Parker, became a major figure in the development of bebop, which features compositions characterized by a fast tempo, complex chord progressions with rapid chord changes and numerous changes of key, instrumental virtuosity, and improvisation.

His full name was John Birks Gillespie. He earned the nickname "Dizzy" for his amusing antics on stage.

His father was an amateur bandleader, so instruments were available to Dizzy at an early age. He started to play the piano at the age of four and taught himself how to play the trombone as well as the trumpet by the age of twelve.

From the night he first heard his idol, Roy "Little Jazz" Eldridge, on the radio, Dizzy dreamed of becoming a jazz musician.

Dizzy recorded one of his earliest compositions, "Pickin' the Cabbage", with Calloway in 1940, but Calloway disapproved of Gillespie's mischievous humor and his adventuresome approach to soloing. During a rehearsal, someone in the band threw a spitball. Already in a foul mood, Calloway blamed Gillespie, who refused to take the blame. Gillespie stabbed Calloway in the leg with a knife. After the two were separated, Calloway fired Gillespie. A few days later, Gillespie tried to apologize, but he was dismissed.

During the 1964 United States presidential campaign, Gillespie put himself forward as an independent write-in candidate. He promised that if he were elected, the White House would be renamed the Blues House, and he would have a cabinet composed of Duke Ellington (Secretary of State), Miles Davis (Director of the CIA), Max Roach (Secretary of Defense), Charles Mingus (Secretary of Peace), Ray Charles (Librarian of Congress), Louis Armstrong (Secretary of Agriculture), Mary Lou Williams (Ambassador to the Vatican), Thelonious Monk (Travelling Ambassador) and Malcolm X (Attorney General).

Deeply affected by the assassination of Martin Luther King Jr. in 1968, Dizzy joined the Bahá'í Faith, which teaches the essential worth of all religions and the unity of all people. Gillespie spoke about his faith frequently, and he is honored with weekly jazz sessions at the New York Bahá'í Center in the memorial auditorium.

Carter (who was nicknamed "The Peanut Farmer") requested "Salt Peanuts", and Gillespie responded that he would play it if the president "will come up here and sing it with us."