I would suggest spending a portion of your practice time (say, 5-10 minutes a day) practicing the jazz ride pattern at a slow tempo (you can add the hi-hat on 2 and 4 and a very light bass drum on all 4's if you want), between MM 40-60. Emphasize the quarter note pulse, and play the skip note relatively lightly, playing it by while lifting the stick to make the next quarter note. Stop the stick (without tension) around an inch above the cymbal on the quarter notes.
In my opinion, Jim Blackley's book Essence of Jazz Drumming has some of the best exercises focusing on ride cymbal articulation, so I'd recommend checking that out if you can (it's a little spendy, but you might find it worth the investment). The time I've spent working out of that book has been very beneficial for my timekeeping, I think.
As I've been monitoring this thread I was wondering if this book would ultimately get brought up and recommended. Since I've done so on various other threads, I was hoping someone else would.
This book has been transformational to me. This is not to discount the amazing library of John Riley which is critical for in-depth study by anyone who wants to gain the insights, musical knowledge and coordination for jazz.
The Blackley book is a different animal altogether and should be an "addition to" not "instead of" the Riley material.
Agreed on all the above. But, I'd say that swinging articulation is key for more than just the ride cymbal. I don't think eddie meant to say that it was, just clarifying to anyone reading.
One of the things I see the most from students and people new to jazz drumming is stiff articulation of nearly every phrase they play whether it be basic time playing on the ride, comping on the SD/BD or solo phrasing. I think the sooner you get into thinking about it and practicing the physical motions required to do it, the better.
Jim's book goes a long way to helping one understand swing articulation but doesn't go into the physical execution for obvious reasons. But, forgetting technique, the most important resource to research is the entire discography of jazz. I think you need to start in the 20s and 30s and work your way forward in time. Whatever you do, don't dive in with modern jazz or even bop. There's just so much going on. Stick to early recordings and/or big band recordings from the 30s, 40s and 50s where the rhythm sections are there to generate a feeling more than be full members of an interactive conversation. If you haven't checked out Gene Krupa with Benny Goodman, you have no business trying to penetrate more modern playing. You can do far worse than to sit down and listen to the entire Count Basie catalogue or Frank Sinatra's swing years with Irv Cottler smacking out backbeats with authority.
Listen to the drummers. But don't just listen to the drummers. We're too drum-centric. Listen to the horn players, piano players and the vocalists, too. Go through an entire album just zeroing on the double bass. That's where you'll learn to articulate - by imitating the way the human voice, wind instruments and the bass play swung figures and trying your level best to express that via the drums. I consciously try to pick up on the way my double bassist phrases their skip notes and put mine in a complimentary (if not the same) place. Listen to how the piano players phrased their offbeat notes and put your skip notes in the same place.
Learn the melodies. If you don't know the heads to the standards, you won't ever swing. Learn to sing the melodies in the correct style, then try to play them on the drums. Start with playing them on one surface (RC or SD, for instance) and then move to trying to play them on the drums. A classic melody like "Sunny Side of the Street" played by - say - Louis Armstrong has a wealth of information in it about how to phrase and articulate.
Sure, you won't always be soloing or playing figures in that way, but I think this exercise will go a long way to helping a student learn to generate the proper rhythmic undercurrent on the drums to support what's going on out front. Because, in the end, it's about what's going on out front (another way of saying "play for the song!") that matters.
Simply put, Step 1 is Imitate.
Imitate. Imitate.