I agree with Harry when it comes to the definition of "in the pocket"... It's all about setting a proper mood, really. For instance, Danny Carey's flamboyant style with Tool probably wouldn't fit into a simplistic Roots song, but I'd say both Danny and Questlove play very much in the pocket!
I personally try to be very cautious and particular with things like drum fills. I make sure they "fill" up the song rather than simply filling up time.
I can't stand hearing a fill that sounds completely separated from the rest of the song. As long as we use our heads and think about the musicality of what we play, I think flamboyance can be an extremely musical thing!
All in all, too often us musicians lack the maturity and feel to know where, when, and how to pop out or blend in with our music.
Myself included, of course...
