Re: playing "outside"
Ornette's Free Jazz is the Bible for free jazz. However, I'd recommend starting Dolphy's Out to Lunch - it's a bit easier to get into and one of the best jazz recordings ever. Then move into Coleman's The Shape of Jazz to Come. Also Albert Ayler's Spiritual Unity, Coltrane's Ascension, Pharoah Sanders Tahuid, I could go on forever!
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