2 things
As a rock drummer who learned jazz after college and pretty much on my own the best way to learn is in a band.
I had gone through Jim Chapins book and art of bop by the time I joined the band and realised very soon I knew nothing about how to interact with the musicians and how to play the form.
So once you have a couple of tunes and you are comfy playing jazz time just hook up with a piano player and a bass player and practice the real book together. No pressure just fun and learning off each other. Ask questions of the more experienced players and try each tune in different feels.
SmoothOperator - I think you are missing the point with both the real book and jazz as a whole.
Jazz is an improvised style of music meaning that beyond the head (main melody and form of the song) which is played at the start and end of a tune anything really is fair game.
Bass players walk differently on different nights, Piano players chhuck in substitutions, lead players add flourishes and solo differently each night. That's the part i really dig about the whole style.
And as a drummer we change our part dependant on the feel, tempo, style, player we are trying to emulate, vibe, crowd, if the hot chick just waved at you etc etc...
In order to account for this you would need 400 charts all written out and carried. Not any easier than a real book...which you can now get on an ipad.
All the info on the song is there and sometimes as a drummer at jam sessions you don't get a chart you just get a....oh this is a medium swing ....1234 go!
Don;t get me wrong. Listen , transcribe, emulate do all of these things but eventually you are going to have to trust your ears and play what you want at that particular moment.
And if it's wrong do it twice....then it's jazz!
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