Over the past few months, I've been trying a little experiment and it's worked quite well. In my own truly nerdy way, I've been ranking almost every some I listen to on my iPhone/iPod and listening to each song until the very end.
Why? Well, now I've got a list of my favourite, most listened-to songs. This gives me the ability to do a couple of cool things:
1) I've set up my iPhone so that it only contains the most recent 150 songs I've bought plus any song that is at least four stars. Now, when I'm on the go, I only listen to new and/or good music
2) I also use Apple's Genius feature a lot on my iPhone. It's fascinating to see what pops up as a recommendation. Some of my songs consistently cluster together whereas others bridge distinct genres. It's almost become a game to figure out which songs can create the best playlists.
This experience is totally different from using Genius on my laptop. I have 10x more music on my laptop, so the Genius playlists are much more homogenous; it's only on my iPhone where I see a bit of serendipity.
3) I've also created a playlist of songs that are rated at least four stars but haven't been listened to for 90 days. It's like coming home to an old friend (just kidding)
4) I've another playlist of songs sorted by play count. It's a quick and dirty way to guarantee that I can find a song that I know I'll like
There is one downfall to this experiment: if a tune doesn't get four stars quickly, it is doomed to be unlistened forever. Assuming my tastes don't shift (an unlikely assumption) this should be fine, but I'd like to think I can re-discover my older music or allow albums to grow on me over time.
I'll have to set up the next experiment to work on that...