From your enjoyment of MMW, you might want to check out John Scofield's funkier stuff. I think Scofield "A Go-Go" you will really like (with MMW as his backing band). And Grant Green "Alive." I think another entry into jazz from the funky side would be, as you mentioned, Miles' stuff from the late 60's. After that you might want to get a taste of modal stuff and then hard bop, etc. to get the vocabulary. From there, you might go to some of Coltrane's "wall of sound" period from the late 50's to early 60's. A great set is the Village Vanguard stuff from '61 either the Master Takes or the Complete Recordings. Once that happens you will be ready for anything!
This is how I got into jazz as a teenager. I really liked improvised rock and roll like the Dead and the Allman Brothers but I was looking for more and more sophisticated music. I got into jazz by listening to Miles Davis' "In a Silent Way." and then started listening to funkier jazz. Then I went back in time and got very deep into Miles' great quintet with Coltrane. Once I heard Coltrane I was hooked. He led me into free jazz and the sky was the limit for me. But without expanding my vocabulary I don't think I would have found the late period Coltrane stuff and stuff like Ornette Coleman as accessible. I still find that my favorite jazz music was from approximately 1955 to 1962. For me, that is the sweet spot.
For soulful females, maybe Nina Simone, Carmen McCrae, Billie Holiday...
Edited by tjkurita - 9/5/13 at 2:07am