Dameron was initially known as an arranger and composer for big bands, in particular for Harlan Leonard and His Rockets in the early 1940s. Dizzy Gillespie (Gillespie, Dizzy) introduced some of his finest songs, including “Good Bait” and “Our Delight”; Gillespie also premiered his extended orchestral work Soulphony at Carnegie Hall in 1948. The small groups Dameron led on the East Coast and in Europe from the late 1940s to the mid-1950s were the height of his achievement; they included outstanding musicians such as trumpeters Fats Navarro (Navarro, Fats), who was his most sympathetic interpreter, and Clifford Brown (Brown, Clifford).

Though he wrote the occasional pensive ballad, such as “If You Could See Me Now” (for Sarah Vaughan (Vaughan, Sarah)), Dameron's songs in general featured optimistic melodies (“Hot House,” “Lady Bird,” “Casbah”) and provocative harmonies, typically based on standard chord sequences. A pianist with a light touch and percussive attack, he seldom chose to solo himself; one of his most acclaimed works, the extended composition Fountainebleau, includes no improvisation at all. Beginning in 1961 he composed scores for recordings by soloists with large ensembles.