Wynton Kelly crafted an absolute gem of a solo on this, his only, appearance on “Kind of Blue”. On the rest is Bill Evans.
Freddie Freeloader, so named after a barman who used to take care of the guys, is a 24 bar Bb Blues. It used to be that a full chorus of Blues is twice 12 bars. This is exemplified in Freddie by the Ab7 at the end of the first 12 bar form.
This landmark album marked the departure from (be)bop. Not only in it’s modal approach but as well in it’s two – harmonically – basic Blues with a little twist each (the other being “All Blues”). I-IV-V (bVII) is played throughout.
Note how Wynton plays behind the head. This little figure becomes the launching pad for his solo. The general sound of the solo is that of the major Blues scale (Bb C Db D F G) which slowly shifts to the minor Blues scale (Bb Db Eb E F Ab) and Dominant Bebop Scale (Bb C D Eb F G Ab A). Never in a hurry he puts phrase upon phrase getting more complex bit by bit.
He starts with four bars of question and answer. On bar 3 he goes up the octave. During the first chorus he basically always plays towards the root or fifth staying very close to the Blues scale.
Bars 9-11 feature the same phrase going down in whole steps, rhythmically a 3 over 2. This figure come back in the 2nd and 4th chorus.
The second chorus becomes more Bebop through use of the bebop dominant scale and the major Blues scale. He now chooses as well the seventh as ending note. Bars 7 and 19 are the same melody just sped up with a couple more chromatic approaches.
The 3 over 2 figure come back in bars 21-23.
The 3 over figure is back in the forth chorus bars 41-43
BTW ever wondered why the tuning of the album “Kind of Blue” is so badly flat? The two track master was running at the wrong speed. However the latest digital reissue is in tune since they discovered that the safety copy was just fine. Quite remarkable that this would take 30 years.