His biographer Alyn Shipton quotes Don Waterhouse approvingly that Gillespie in the fifties “had begun to mellow into an amalgam of his entire jazz experience to form the basis of new classicism”. Another opinion is that, unlike his contemporary Miles Davis, Gillespie essentially remained true to the bebop style for the rest of his career.
In 1960, he was inducted into the Down Beat magazine’s Jazz Hall of Fame.
During the 1964 United States presidential campaign the artist, with tongue in cheek, 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 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). He said his running mate would be Phyllis Diller. Campaign buttons had been manufactured years ago by Gillespie’s booking agency “for publicity, as a gag”, but now proceeds from them went to benefit the Congress of Racial Equality, Southern Christian Leadership Conference and Martin Luther King, Jr.; in later years they became a collector’s item. In 1971 Gillespie announced he would run again but withdrew before the election for reasons connected to the Bahá’í Faith.