Now I know...
Inspired by a friend of mine, I've spent the last few months listening to my mp3's in alphabetical order. This is not a minor undertaking, seeing as my collection holds 13,641 songs as of this writing. It is, however, the ultimate shuffle/random mode. I've found shuffle on my various players (Zune right now, iPod previously) tended to revisit the same artists over and over...but this listening method results in a truly random order of artists/albums/genres. The only issues I've run into are songs appearing on multiple albums, or also having instrumental versions. In such cases, I'll listen to the second version, unless I truly can't stand the song.
Of course, I haven't stopped buying new music, and a new album can only sit around for so long before I need to listen to it. My compromise has been to listen to any new music I acquire once in its entirety, and then resume the alphabetical project.
The final problem is that sometimes I just want to listen to music normally...picking out a specific album, something I know and love, and playing it the whole way through. There's not really a solution to this...I just have to try and keep it to a minimum in favor of the larger project.
Anyway, here are the sobering stats thus far:
A - 563 songs - 26 days (10/29/09 - 11/24/09)
B - 978 songs - 52 days (11/26/09 - 1/17/10)
C (in progress) - 193 songs - 13 days (1/18/10 - )
That's a total of 1,734 songs listening to in 94 days. Assuming that I listen to the remaining 11,907 songs at about the same rate, it'll take me 645 more days to get through everything.
645 days from today is... November 7th, 2011.
It'll be interesting to see how close to that date it actually ends up being. I'll post some updates on this alphabetical listening project as it slowly marches forward.