Take a look at this concert calendar. It’s personalized for me, pops up in iTunes, and makes it really easy for me to keep up with both concerts by artists in my iTunes library and new music released by those artists.
I’ve had the iConcertCal plug-in running inside iTunes for a couple of years now, and while finding the calendar isn’t easy enough (see the menus? “View/Visualizer/iConcertCal?” REALLY?), the other thing that iConcertCal does is when I play music in iTunes by an artists with some piece of upcoming information, it pops up a reminder. It’s really pretty cool.