Take Jamie Cullum on that list as the perfect example of how to successfully straddle being contemporary AND respecting the past, and push to improve yourself.

I don't see it as an 'either/or thing', Russ... It's possible to do BOTH (and have quite a bit of success in the process). But a head is a head... if you are trying to push yourself eking complexity out of some of the simple basic changes to many of the great standards, why not try to eke out the same complexity out of some of the simple modern tunes, too... Bet you'd get quite a few nods from the kids jazzing up a U2 tune, Coldplay, Jason Mraz, etc..

Let's face it, the jumping off point for a jazz exploration isn't really THAT important. A lot of our favorite jazz was great players spicing up the 'pop' tunes of their day, or generation...