My portable music player is Web connected (probably through a bluetooth connection to my phone, or because it is my phone - the jury is still out on whether devices should include as many features as possible, or do just one thing very well).
This allows me to learn more about the artists biographies and musicographies while I listen to them; I had never been able to remember who was singing what, but now that my music player displays this information on demand as soon as I want, I certainly look much more knowledgeable than I ever did!
Plus, being able to read the lyrics and their translations, downloaded directly from the Web, while I listen to the music makes it finally possible to enjoy fully my music collection, even the parts of which I never quite grasped.
Also, my player now keeps up to date my social network records of what I'm listening, and sure enough I'm starting to discover new titles from my friends records.
But my favorite feature is how my music player compares my listening habits to other people's, and suggests titles and artists that I might like: I end up buying and downloading the selection more than half the times, and the more it goes, the more it finds stuff I had never even heard about before.