iTunes is a good example of this. Basically, Apple took a nice Mac jukebox program (SoundJam) and streamlined it (which meant dropping some of the features and flexibility). Nothing that iTunes does is any more elaborate than, say, what you can do with the RealJukebox (which I what I use on Windows) or MusicMatch (both of which have a lot more features that most people will never use). The most important features that iTunes gained by version 2 had to do not with options but with Apple's digital hub strategy: burning CDs and synching to the iPod (and, don't forget, other music players).
Version 3, however, seems to focus more on what's useful information when listening to music: keeping track of what you've listened to (and when you last listened), how you rate it, and additional information like a composer property which is very important if you listen to classical music. But the cool part is that you get to write simple rule-based “smart playlists”” that can exploit all this information. (And all this state will sync up with an iPod, including the place you last listened to in those books from Audible.com.)
For example, I am a bit of a music pack rat (oh really ?), so I have a smart playlist which is simply all the tracks I've never listened to. So now it's a lot easier for me too keep track of all the good stuff that folks through my way, and I can actually make good on my promises to check their stuff out. And the lists from these rules update the display dynamically, which is cool.
Of course, my Never Played list was frighteningly large (still is). Besides the things I've packratted, I've ripped stuff for other people that I myself hadn't listened to in a while. And there's also the stuff I listened to before I got iTunes 3 but not since. Days worth, actually.
So, in a silly bid to get the song count down, I sorted the list by time, shortest first. It was like listening to a radio station programmed by a demented yet hardworking and eclectic DJ — mostly joke tracks or intros and small ambient pieces, but also micro-songs by the Bongos (there are a few on Drums Along the Hudson) and lots of mood pieces from Geogaddi by Boards of Canada. As it turns out, that album has at least six tracks that are under a minute in length, very moody indeed !