Music Programs and Genres or Who Goes Where?

I've resorted to a blanket "alternative & punk" category (which would also technically include post-punk, indie, whatever) that would pretty much cover everything you just listed. All of the lines between those sub-genres are too fine to make any distinctions that hold true through an entire artist's career (early Costello - punk? Almost Blue - country? Imperial Bedroom - pop? Blood and Chocolate - rock?). And, yeah, I hate the word "alternative," but a lot of stuff I have automatically has that word assigned, anyway, so I'm just going with the flow.

I use "Rock" for pretty much everything rock-based that doesn't fit into those categories (Springsteen, Zeppelin, the Who), although I arbitrarily use "pop" for the Beach Boys.

Hip-hop's obvious, jazz is obvious, classical's obvious, etc.

I have an Avant-Garde category for the culty hard-to-categorize, record-store-assholes-eat-this-shit-up stuff like Scott Walker, Serge Gainsbourg, solo Nico (but not VU, for some reason), and John Zorn. I think I have a Krautrock category for Can, Neu!, and Amon Duul II, but I could probably just fold that into the Avant-Garde thing.

On a related note, I can't make up my mind on whether or not to differentiate between, say, Neil Young and Neil Young & Crazy Horse. Or Ben Folds and Ben Folds Five. Or Prince and Prince and The Revolution and Prince and the NPG. Tom Petty. Ben Harper. And so forth. It would look so much neater if I labeled them one or the other, but would be factually inaccurate.

Since I can't solve this quandary, ain't no way I'm even gonna attempt to tighten up the genres.

You're anal? I'll bet I'm even analer about some of it. But, when it comes to genre labeling in iTunes, I'm a little lazy. I do this sort of thing:

- Otis Redding: R&B/Soul
- Funkadelic: R&B/Soul
- Pearl Jam: Rock
- The Clash: Rock
- Battles: Rock
- Miles Davis: Jazz
- Weather Report: Jazz

OK, Otis Redding is all good. Funkadelic I could file under "Funk", but then I have to take James Brown into account. A lot of JB's music doesn't fit into that category, but a lot does. Same for Stevie Wonder and Sly and the Family Stone. Ultimately, "Funk" has to fuck out of the equation for me. Then there are groups like Fishbone and Battles - very different from one another - but neither is easy to classify under any one genre I've heard of. Battles isn't really even avant garde, in my opinion. Nor are they "math rock" according to the band. You could argue that Fishbone is ska, funk, soul and/or rock depending on the song. I have no trouble accepting everything Miles Davis as "Jazz". Weather Report either, really, unless you want to throw the term "Fusion" into the mix. But then there are different types of fusion if you want to muddle things up to ridiculous degrees. I guess the bottom-line on all this is to try to keep it simple for yourself.

Two bigger quandaries for me:
1) Duets/collaborations. I have the Marvin Gaye box set and he has several songs with different female singers. On the one hand, I like having the option of viewing who he sings with on a particular song. On the other, I might be in the mood to shuffle all of Marvin Gaye's songs. But that can't easily be done without removing the names of the women he sings with and simply tag them all "Marvin Gaye" as the artist.
2) Multi-performer soundtracks and various artist compilations. Don't know about you, but I find scrolling through album titles on my iPod very tedious. It's much easier to select an artist. But there's no other good way of listening to anything with various artists apart from searching by album title. So I just deal with it by opting to leave the names of the multiple performers off and hopefully still know who I'm listening to.