There are some records that you will find very hard to listen, I mean, free jazz is kinda hard to listen at a first glance.
I agree.
Unless you start in a live setting with really great players. I have a lot of friends who are into it after stumbling upon a live show here and there in NYC/Chicago.
Listen to as much music as you can. If you like an artist (not just drummer) - go find 10 more albums with that guy on it - and keep doing that. Keep branching out and discovering new players, new styles of play, etc. (those 60's Blue Note albums are a great place to get to - Wayne Shorter, Tony Williams, Grant Green, Joe Henderson, Horace Silver, Jazz Messengers, etc etc etc). Listen to what's going on in the music, and listen to what each player is providing the moment. What kind of bass line is going on? What's the drummer giving the group? Pianist? What's the instrumentation? Full rhythm section? If not, listen to how the drummer provides the time as opposed to another recording w/different instrumentation. Is the bassist providing a walking line or something more broken up? how's the drummer augmenting this?
play along to those albums. Play along to every single one. Every song. Don't skip the ballads - get into the ballads! Try playing like the drummer. Try doing your own thing. (these last two items will take a while to get to - I'm getting ahead of myself...let's backtrack)
Practice practice practice! I started my jazz excursions with Jim Chapin's book and eventually found my way to the Alan Dawson stuff using Syncopation and Stick Control (someone else mentioned Ramsay's book - probably the best thing you could pick up in terms of books) and still working on the first exercises.
ALWAYS WORK ON YOUR FUNDAMENTALS. There's a reason Tim Duncan is one of the greatest power forward/centers of all time (he is) - and it's his ridiculous fundamentals he developed. When I studied with Nasheet Waits (8-9 years ago), he said "great hands. no fundamentals to know what to do with them" - and demonstrated by playing very basic jazz things at ridiculous tempos and they sounded so damned good - I thought "Wow, I have so much to work on" and it was the stuff I always thumbed my nose at or avoided: FUNDAMENTALS. Feather that bass drum '4 on the floor' - get those hats crackin' - 2 & 4 and all 4 - try fast try slow - try different dynamics. Make sure the ride has good articulation (controlled by the pressure of the fingers/grip). Get those basics going and get them *sounding good*. I'll hear someone "play jazz" and think "Nope! Not happenin'!" Get those basics sounding good and then the comping will come a little more naturally. And everything will be happening on a solid foundation that you can choose to stick with or move away from - but it's always there. After Nasheet told me that line, I remember practicing the basics for 10 hours a day for months and months straight - ignored everything else and just did basics. He told me he worked on that first page of Syncopation for years - just fundamentals - and that floored me. Here he is doing all sorts of crazy stuff and it came from working on the simplest stuff... I remember seeing Yoron Israel play at this camp a few years before the Nasheet stuff and seeing him playing all this crazy stuff and keeping the feathering going the whole time except to bust out some bombs on the bass drum here and there and going back to feathering without missing a beat - and being thoroughly impressed - but didn't [at the time] equate that into something I needed to work towards...not sure why...
I listened to an old All-State jazz CD a while back (ah nostalgia!) and thinking "My gawd, I sound so thin...so just-barely-getting-by" and the other drummer (they take two every year) was leaps and bounds ahead of me (Connor Elmes - went to NEC and studied with Bob Moses - great player). That was my wake-up call, like "Okay, there's more to this jazz thing and I need to learn it now!" That summer (17 years old) was when I started really hitting the books. Also when I was finally introduced to Elvin Jones via Robert Kaufman (thanks Bob!)
Listen.
Practice.
Play.
