Bebop's lifespan was relatively short as a radical movement. Despite the style's tremendous influence on jazz and jazz musicians (which continues to this day), bop in its purest form dominated the music scene for about only five years—from 1942 to 1947.
Bop's beginning can be dated roughly from Charlie Parker's recording of Cherokee in September 1941 to Miles Davis's Milestones of August 14, 1947.
Milestones is a critical jazz recording for two primary reasons:
First, Milestones was one of four tunes recorded by Miles Davis during his first outing as a leader at age 21 for Savoy Records. The Miles Davis All Stars, as the group was billed for the session, also featured Parker playing tenor for the first time in a studio.
Second, Milestones was radically different from other small-group bop arrangements and recordings up until that time. It's even different than the other three originals Miles composed and recorded that day (though Half Nelson is close). What makes Milestones significant is that it contains distinct traces of a new modal jazz style that was emerging and would soon become known as "cool."
Of course, when Milestones was recorded in August 1947, the Birth of the Cool band was a year away from appearing at the Royal Roost nightclub to showcase the new music and a year and half away from a studio date in January 1949.
Yet Milestones signals a change in the musical weather. Bop—with its flatted fifths, complex riffs and staccato runs—was a showcase for speed and agility. Cool, by contrast, would promote longer musical lines and a more relaxed pacing. Milestones' sound was new—even if it wasn't recognized as such at the time.
Miles decided to use John Lewis on piano for the Milestones session in 1947 instead of Duke Jordan, the pianist in Parker's quintet. This was significant. Miles felt Lewis had a more progressive sound and believed he was a better musician. Lewis is also rumored to have been the composer of Milestones with the breakthrough arrangement by Miles.
After this date, Miles pushed Parker to replace Jordan with Lewis. Here's Duke Jordan's take from a sour-grapes interview in Brian Priestley's book, Chasin' the Bird (2005):
"Miles was tight with John Lewis, and he wanted Bird to substitute John for me in the group. But Bird silenced him quietly, firmly saying that he chose the guys and Miles could form his own outfit if anything displeased him. That was all that was heard from Miles."
If Jordan sounded bitter about Miles, he was. Miles and Jordan didn't get along. Miles explains why in Miles: The Autobiography (with Quincy Troupe/1989):
"Nobody could keep up with Bird back in those days except maybe Dizzy [Gillespie]. Every time [Bird would solo], Max [Roach] would scream at Duke [Jordan] not to try to follow Bird [on piano]. He wanted Duke to stay where he was because he wouldn't have been able to keep up with Bird and he would have fucked up the rhythm. Duke did this a lot when he didn't listen. See, when Bird went off like that on one of his incredible solos, all the rhythm section had to do was stay where they were and play some straight shit. Eventually Bird would come back to where the rhythm was, right on time. It was like he had planned it in his mind. The only thing about this is that he couldn't explain it to nobody. You just had to ride the music out. Because anything might happen musically when you were playing with Bird. So I learned to play what I knew and extend it upwards—a little above what I knew. You had to be ready for anything."
By the summer of 1947, Miles was also a step ahead of the boppers, musically. While the Birth of the Cool ensemble wouldn't start playing publicly until September 1948, the musicians who would form that band were already meeting regularly at arranger Gil Evans' New York apartment.
Evans was arranging for Claude Thornhill's progressive band and was at the vanguard of a new wave of advanced musical theories. Tiring of the pat formulas and relatively simple arrangements played by small bop groups, Miles was eager to weave Evans' complex theories into his own playing. Miles would do this for the first time on Milestones.
If you listen to Milestones of 1947 (not to be confused with Milestones from 1958), you can hear that it is a considerable break from what was being played at the time and served as something of a salvo across bop's bow. Cool was coming.
By the end of 1948, Miles was out of Charlie Parker's group after a dispute over money, differences over the group's pianist and tensions that typically arise when great musicians have different visions. Miles was replaced by Kenny Dorham, and Duke Jordan was replaced by pianist Al Haig.
Miles would go on to lead and record Birth of the Cool (with John Lewis on piano on most of the dates). The rest, as they say, is history.
Wax tracks: Birth of the Cool (1948-1950) formally introduced jazz listeners to a new, more sensitive approach, but Milestones documents where cool was conceived.
One of the best ways to listen to Milestones is on Miles Davis: Complete Savoy & Dial Recordings. It's available here at Amazon (or download the tracks mentioned on various albums at iTunes).
I love listening to Milestones on this CD because it's preceded by Bird's Buzzy (May 1947). When you hear Buzzy and then Milestones, the departure is instantly clear. You can really hear the end of one musical era and the start of another.
Listen how pretty Miles is playing. Not frantic or rushed. Just long and smooth, hanging on notes and drawing large arcs. Interestingly, Bird's tenor playing on Milestones is a hot and slippery—his solo sounds eerily like Lucky Thompson—and he isn't quite in sync artistically with what Miles is trying to achieve.
With Milestones, you can hear the music change—and listen as one great jazz musician breaks artistically from his mentor.
Wax clip: While there's no footage that I'm aware of the Birth of the Cool band, check out this clip of Jeru by the CAPA High School Saxophone Ensemble. Jeru (baritone saxophonist Gerry Mulligan's nickname) was one of the songs performed on the Birth of the Cool album.
Not bad for kids. The point being that this music was written in 1947 and 1948, and clearly was way ahead of its time when you consider what was mainstream in jazz then.
Like the glass and steel architecture, and abstract expressionist painting of the same period, cool was a celebration of sensual simplicity and space.


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