When I heard him on “Jazz with Bob Bazooka” or whatever, I thought it was Felonious Monk.
Let’s see, appears no one’s mentioned Grant Green - check out Idle Moments which is kind of his definitive album, and Matador, which is less well known but wonderful - and it includes his own arrangement of “My Favorite Things”.
Certainly delve more into Coltrane - Blue Train, Giant Steps, and Ascension (though, as with all his post-A Love Supreme work, Ascension is pretty out there) are often considered classics, and there’s also Crescent, which is one of my personal favorites.
Let me second the recommendation of Sun Ra. I like Lanquidity quite a lot, and it’s a little more accessible than some of his other stuff. Art Ensemble of Chicago is also avant-garde, yet generally very listenable as well.
Lately, I’ve been listening a lot to Radiale by the little-known Spaceways Incorporated after getting a recommendation from the people at the record store. Great album, very strongly influenced by Sun Ra.
Dave Douglas is one of the people still doing interesting stuff - check out Freak In or The Infinite. His associate John Zorn is probably the most avant-garde jazz musician around today, and I just love his now-defunct klezmer/jazz group Masada.
There’s also some Great White North Jazzers to celebrate. They’re harder to find but still very musical.
Diana Krall - Piano and vocals
Mike Rud - Guitar
Mike Murley - Saxophone
David Braid - Really kicken bombastic Piano
David Occhipinti - Guitar
Mike Herriot - Trumpet
Oscar Peterson - Probably mentioned above
Brad Turner - TPT
The Band Metalwood - Cool electronic stuff