Because there isn't a pair of headphones in the world that will organize your songs for you.
So what do you use for that? I assume most of you use digital means for that; though perhaps not. A select few might prefer vinyl, or perhaps they just won't trust a PC with their CDs. To each his own. For me, the advantages of digital storage, organization and playback are just too great.
Currently, I use iTunes for this. This is solely because of smart playlists. Maybe some of you feel the same way. Nothing can quite match what you can do with those playlists. On a basic level, I can tell itunes not to play any songs that I've already heard or already skipped in the last week. I can exclude by genre, add date, rating.... Most notably, I can sort by comments. This feature is deceptively useful. It lets me exclude or include songs based on keywords I've placed in the comments field. It lets me create my own set of associations and significances between songs. For example, I have a comment labeling songs that include "adult content". These songs can be excluded if I am in the company of someone who would rather not hear that. I have a "top 40 September 2012" comment, and one for all corresponding months, listing the more common radio music. One of my favourite uses of this feature is to have a comment for each of my friends. I'll tack a friend's name onto a song if they say it's one of their favourites, and include that comment in a playlist next time they're listening. Alternatively, I can EXclude songs based on friends' preferences, and keep them from being played when they're around.
Unfortunately, this system is still lacking. For example, if I'm playing music from my phone with two friends, I'll want to exclude the music they dislike. But what if another friend joins up? I have to go back to my laptop and create another playlist with itunes. If you think it would be possible to already have a playlist for every possible combination of comments, then you're misunderstanding how fully I use this feature. The ideal way for this to work would be far more fluid. More like a tagsorter than a preset playlist maker. Unfortunately, I haven't found anything that will do this, not to mention sync it to my phone.
I'm constantly looking for alternatives.... I've heard that Windows Media Player has some decent "auto playlist" settings, but I don't think it can quite match itunes. I tried out DoubleTwist for a while as a way to get my music to my Android phone, but then I found iSyncr. It lets me sync iTunes smart playlists and everything to android -and here's the kicker- syncs new ratings and playcount data BACK to iTunes. Impressed me for only $3 or something.
So; what do you guys use to sort and play your music? What's the consensus on iTunes; are you willing to put up with its obnoxious Apple-ness as long as it has some cool tricks? Do you use just a stock player that has album / artist / song sort fields? What's your favourite metadata editing program, or do you prefer a certain program for ripping your CDs? I never really hear about these topics on Head-Fi, so I thought I'd ask.