Probably one of the best educations in jazz could be had by beginning with the Ella Fitzgerald songbooks. The ones I know the most intimately are the Cole Porter and the Rodgers and Hart, but there are also the Gershwin, the Johnny Mercer, Harold Arlen, and Ellington collections. And one I'm forgetting; i think there were seven?

Anyway, the idea would be to get a grounding in the classic songs, sung in a calmly swinging but still fairly *straight* way. (After that I would move on to the high modernist canon of Mingus, Monk, and Miles.) She doesn't alter the melodies too much or get too cute or mannered. Ella, like Sinatra, is a great jazz musician, and Nelson Riddle's arrangements serve them both well. The idea of doing songbooks itself is a stroke of genius, because it gives the singer like Ella a repertoire that is at her musical level, rather than making her depend on whatever songs some record producer happens to think will be hits. Imagine if Billie Holiday could have made a Gershwin songbook.

Vocal jazz of a certain always intersects with plain old "pop" music. Bing Crosby, Nat Cole, Sinatra, Ella, Dinah Washington, etc... There were the commercial pressures, and also the fact that jazz simply *was* the pop music of a certain period. Not all pop was jazz per se, and not all jazz was pop, but the dominant idiom was swing-based jazz.

The rejazzification of certain figures, at a somewhat later date, is interesting to consider in this context. Take Tony Bennett, for example. Once pop music was not as jazz based, Bennett could do more pure jazz work than before. Norman Granz recorded Ella and Sarah in a later period in contexts that highlighted their jazz roots. Ella with Joe Pass, for example.

Rather than seeing this pop elements as an impurity in jazz, I see it as a healthy complement. Vocals will always be more popular than purely instrumental music, so the most popular jazz musician today is probably Diana Krall. Maybe it's a generational thing, but I prefer to go back to Ella.