y’know, I like the idea of music files being able to contain their own metadata, so media players and car stereos can index them. So why does everyone fuck it up? I go to iTunes store and buy an album called “The Best of DMX.” I expect the artist to be “DMX.” Which means, of course, that in iTunes it’s broken up by artist to “DMX,” “DMX & Sheek,” “DMX & Sisqo,” and “DMX & Mother Teresa.” why do they do this?
Name 'em whatever you want.
An album with multiple artists should be marked as a “Compilation”. Then, even if one track is “Barry Manilow with Macklemore” and the next is “Barry Manilow featuring Paul Oakenfold”, it’ll stick together as one album.
You can always go in and change all the tags to anything you want (I’d go with “Beery Moonilow”).
I always go through iTunes and delete the “album artist” field to resolve this exact problem… So annoying, not that much punk rock is titled with “feat. DMX”. 
Ummm, filling the album artist field avoids this exact problem. When the whole album has DMX as the album artist, it doesn’t matter how many “feat.” are on the album, it will show up as one album in iTunes. You can also really go crazy with “Sort [artist, album artist, whatever]”, a really nifty feature of iTunes. For instance, you could have P!nk with her correctly spelled artist name and still have it sorted as “Pink”. For “The” iTunes adjusts this automatically.
Based on the artist tags I inherited in my MP3 collection, I have found that many people seem to think that Bruce Springstein, Bob Dillian and Bob Marley are the artists for any song that shows any similarity, no matter how remote, with their styles.
I guess I’m a minimalist, I usually just erase the “feat. Xyz” from the artist field altogether. You’re absolutely right, though, about the usage. Must stop posting while tired.
iTunes is fucking with you because you intentionally spent money on a DMX album.
I have never had “Bruce Springstein” or “Bob Dillian” pop up in any artist search. 
I have.
A significant percentage of my old-timer rock music sung by a man who isn’t feminine was apparently composed by Bruce Springstein, Bruce Springstien or Bruce Spingsteen according to the tags I inherited. I learned some things from those tags though. I had no idea that Bruce sang Jesse’s Girl until I burned it to a CD and played it in my car. The same is true for Bob Dillian, Bob Dillen, and Bob Dillon. I had no idea he sung American Pie until the tag told me.
Billy Joel is equally impressive and sings everything from Piano Man to Leader of the Band. None of those white guys can match the range of Bob Marley however. He did the usual reggae songs like Don’t Worry Be Happy according to the tags but also branched out into other genres like rap and composed songs like Because I got High even after he supposedly died.
The problem with “Compilation” is that iPods then remove those songs from under the “Artists” listing. And considering that I use Artist view 99% of the time… I mainly use “Album Artist” and set it to “Various Artists” for compilations, then you can retrieve the album artwork automatically, no problem. In iTunes, there is also a separate tab called “Sorting” that you can adjust. It’s still mostly trial and error, though.
In my experience, “featuring” = hip hop, “with” = other genres. “vs.” is a mash up.
Personally, I would move the “with” part to the song title. So “DMX feat. Swizz Beatz - Get it on the Floor” becomes "DMX - Get it on the Floor (feat. Swizz Beatz).
I hate! looking at other people’s iPods. It makes my OCD ping to see the same artist listed 8 times under slightly different names. But for the sake of consistency, I renamed all my Stooges as Iggy Pop.
ETA: only more annoying is what Shagnasty mentions. My estimation about someone’s worth lowers when I see how every reggae song is labeled Bob Marley, or every comedy song is Weird Al on their iPod. All stoner white boys are Sublime.
OK, OK, I was whooshed. I have seen examples of this very thing and also, as thelurkinghorror mentioned, all song parodies tagged as Weird Al, whether he or Bob Rivers or Johnny Crass made it. Random people on the internet is stupid.
But everybody knows Madonna sang “American Pie.” 
Ugh, yeah. No OCD here, thank god, because my stuff is a mess. I had an old 30-gig iRiver that didn’t care about tags, the interface was just like Windows Explorer–I’d create a folder called “Yes” and then a subfolder called “90125” and when I ripped the CD, I’d just put the files in that folder.
But it got old, the battery, the battery got shot, and I ran out of capacity. So I bought a Zune off of some incorrect advise that it did much the same thing. Instead, it goes off of these tags, and I found to my horror that all of the rips I’d been doing with Audiograbber using Freedb for the file names and tags have messed things up normally.
Even putting aside “Yes” vs “Anderson, Buford, Wakeman and Howe,” or “Thomas Dolby” vs “Dolby, Thomas” and possible misspellings–I found out that a lot of people dealt with the 20-minute Yes songs that are named with different “parts” by using “Yes” and the artist name for the album in the tag, but then using the main song name as the artist name and then the part name as the song title names to try and get the information in. So that if I go by artist name, I suddenly had things like “Close to the Edge” as an artist.
I’ve slowly been correcting some of them, but it’s probably over a third of my collection that was screwed up in some way.
Honestly, the idea of multiple artists should have been built in from the start. Even before the whole “featuring” craze you often had multiple people contribute. Wouldn’t it be great if you could list a band and its members, so you could listen to all music played by that one guy?
And it’s not even like all audio files are music, even if the taggers seem to think so, with only one standard category for spoken word.
For real. Classical music is also very hard to squeeze into this grid. Imagine a four-movement symphony: it’s four “songs”, but it’s one work. It’s not an album, because that CD also contained a piano concerto. How do you keep them “together”? Opera is worse: there is be no way do deal with the multitudes of singers in any given track (because cluttering up the artist field is no good, either - that’s where the conductor goes, possibly the orchestra as well). It would really be nice to have the option to search for all tracks with the Berlin Philharmonic, or conducted by Abbado, or featuring Lang Lang, be it solo or chamber music, or with an orchestra. Alas, all that has to be dealt with by grossly abusing the system that we are given.
I have always hated that tagging data with a passion.
Is it “Guns And Roses” or “Guns & Roses” or “Guns N Roses” or “Guns ‘N’ Roses”?
Every track I have is stripped to the bone of any tagging data and the file is renamed “Artist - Song.mp3”.
Well, that doesn’t really solve the problem, does it? You still end up with some “Guns And Roses”, some “Guns & Roses”, some “Guns N Roses” and some “Guns ‘N’ Roses”, right? And what program does the sorting and archiving of those barenaked files for you? Tags are a great thing if you know what to use them for, they really are!
Oh yeah. For a Beethoven piano concerto, for example, is it more approrpiate/useful to identify the “Artist” as the soloist, the orchestra, the conductor, or Ludwig himself? And there are all sorts of ways the track/movement titles can be labeled.
Am cursed with managing separate “Bjork” and “Björk” folders and all of the duplicatey-shuffly joy it brings.
If there only was a way to turn all those “Bjork” songs into “Björk”…