Jazz trumpeter Chet Baker, the Samson of jazz, is described on Allmusic as "a tragic figure with immense talent...his career was marred by drug addiction." While he could have been one of the greatest jazz musicians of all time, he is not as well-known as some jazz musicians because he failed to take full advantage of his musical abilities.
A look at his discography shows how much he recorded, and according to Wikipedia, he recorded for Pacific Jazz, Barclay, Riverside, Prestige, SteepleChase, Columbia, and RCA.
This article will focus not on a recording done in his early career, but instead focus on a recording that was done in his later career - 1985, in Bologna, Italy. He recorded a live performance in the city at this time with just a guitarist and a bassist (probably a bass guitarist).
Of particular note on the album is Chet Baker's version of "Tune Up", a Miles Davis composition that is a jazz standard. Listening to this recording requires patience, since Baker's best playing is not at the start; however, his long solo on this version is one of Chet Baker's great recorded solos - there are, of course, many other great solos he did that unfortunately were not captured on a recording device.
This version of "Tune Up" does not begin in a particularly unusual fashion. He begins playing the tune solo, and as the melody progresses, a guitarist begins to accompany him, and then the bass begins to play accompaniment. There are no drums on the recording.
Shortly after he begins his improvisation, the guitarist stops playing, and unfortunately - with only the bass for rhythm - Chet Baker struggles to find the rhythm. Then the guitar enters about a minute and 15 seconds into the recording, and suddenly Baker bursts into full, productive improvisation. The recording becomes one of those where the level of tension is clearly increasing, but the musicians are in total control of the music. It is both tension and release at the same time.
Baker's phrases cannot easily be explained with words because it makes so many things about his music seem like contradictions. His phrases are logical and not logical at the same time, they are joyous and mournful at the same time, etc. As his solo progresses, he reaches a level of bebop phrasing that few have matched - controlled, and so often perfectly timed so that you can almost feel where the phrases will go when they have hardly started; yet, Baker is still often unpredictable. He does everything right without following any of the standard guides for improvisation - he seems to have no worries about where to build to a climax, begin, or end a phrase. He just plays what he wants on his trumpet with no consideration for "rules" of improvisation.
The guitar improvisation, after Baker's solo and by Philip Catherine, is different in some parts, and not others. It has sections with bebop phrasing and others that sound similar to the kind of music that was played before jazz existed. When he plays bebop, he proves himself to be a good improviser.
After a bass solo, which unfortunately is hard to hear because of the guitar's accompaniment (bass solo by Jean-Louis Rassinfosse), Chet Baker returns and closes with the tune.
This is a recording really worth a listen, especially for the trumpet solo, which can be greatly inspiring to musicians in the bebop subgenre of jazz.
*Information about musicians: https://www.allmusic.com/album/live-in-bologna-1985-two-a-day-mw0000735241