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In several liner notes the word "Freebop" is used to describe the music of Miles Davis' second quintet in the mid-60's. The writers usually use the term seemingly expecting the reader to know what it meant, but never bothering to define it or say what makes it "Freebop."

Where did this term originate and what exactly makes something Freebop? Does it apply to anything besides Miles' second quintet?

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As far as I can tell, Freebop is a combination of Free Jazz ("Free") and Bebop or Hard Bop ("bop"). Miles Davis's second quartet was certainly playing a hybrid of those two types of jazz at the time. Today that hybrid style of jazz is more frequently referred to as Post-bop, I believe to be a bit more all-encompassing for other artists recording similar jazz around that time.

However, as for Freebop specifically, Wikipedia has some information on why their music was called "freebop".

The quintet's approach to improvisation came to be known as "time no changes" or "freebop," because they abandoned the more conventional chord-change-based approach of bebop for a modal approach.

Unfortunately, I can't seem to find any contemporaries of Davis's Second Quintet specifically being called Freebop, but I have been able to find a few more modern jazz artists associating themselves with Freebop.

However, if you look at Freebop as a part of Post-bop, and are looking for artists within that subgenre, it seems to be much easier to find similar artists. Check out the Post-bop Wikipedia page (also linked above) for more information.

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I think most of Ornette Coleman's early quartet and trio recordings could be reasonably called freebop. It all burns and swings like mad while imposing no harmonic or other constraints on how the players respond to the material presented by the tune. The fact that the quartet's front line is sax and trumpet and the use of the head-solos-head structure conjures Charlie Parker and Dizzy Gillespie. Also phrasing though extended and free-er, is in the vein of Parker and Diz, and Miles (actually Don Cherry brings more of a Miles flavor to the table than he does Dizzy). All of the above goes for Mile's 60s quartet, Other examples include early Cecil Taylor, Prince Lasha, Steve Lacy, for instance. Ironically, Miles disparaged Ornette when his quartet came to New York around 1958, as did Charles Mingus and others, but they mostly came around to the free player's way of thinking in their individual ways.

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