During these same decades of the 1950's and 1960's, some musicians took jazz in more exploratory directions. The terms free jazz and avant garde are often used to describe these approaches, in which traditional forms, harmony, melody, and rhythm were extended considerably or even abandoned. Saxophonist Ornette Coleman and trumpet player Don Cherry were pioneers of this music through albums such as The Shape Of Jazz To Come and Free Jazz. The former album, as well as several more recorded with a quartet that also include either Scott LaFaro or Charlie Haden on bass and either Billy Higgins or Ed Blackwell on drums, still retains the basic feel of traditional post bop small group jazz, with alternating soloists over a walking bass line and swinging drum beat. This style is sometimes known as freebop. The album Free Jazz was a more cacophonous affair that featured collective improvisation.

Another major figure in the avant garde movement was pianist Cecil Taylor. His playing is very percussive, and includes dissonant clusters of notes and fast technical passages that do not appear to be based on any particular harmonies or rhythmic pulse.

John Coltrane, as already mentioned, delved into the avant garde in the mid 1960's. Albums such as Ascension and Interstellar Space show Coltrane absorbing both Free Jazz and the works of Cecil Taylor. Later Coltrane groups featured his wife Alice on piano and Rashied Ali on drums, as well as Pharoah Sanders on tenor saxophone. He also recorded an album The Avant Garde with Don Cherry that is interesting for its parallels with The Shape Of Jazz To Come and other Ornette Coleman quartet recordings. Coltrane influenced many other musicians, including saxophonists Archie Shepp, Sam Rivers, and Albert Ayler.

Sun Ra is a somewhat enigmatic figure in the avant garde, claiming to be from the planet Saturn. He plays a variety of keyboard instruments with his big bands that range from 1920's style swing to the wilder free jazz of Coltrane and others.