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The iTunes method of organizing files is horrible. I manage my own, and have been doing so since before I switched to Mac and iTunes. My method is much better organized than iTunes.

An easier and more effective approach is this:
  • Put only the song name in the Name field.
  • Put the actual artist performing in the Artist field.
  • Put "Various Artists" in the Album Artist field.
For soundtracks, do the same thing. Soundtrack name in Album, song name in Name, artist name in Artist, and "Various Artists" in Album Artist.

For a song to sort together, all tracks must have matching data in these fields:
  • Album
  • Album Artist
  • Sort Album
  • Sort Album Artist

But wouldn't I have a bunch of albums titled "Various Artists" then?
 
That's my point though -- if you're going that generic in your genres, what benefit does it have over just having all artists in a single folder. Seems like it's just an added layer for not much benefit. *shrug*

PS - Not trying to be a jerk, hope you know that -- I'm honestly interested in how you organize your library. My music library just passed 1.8 TB (just music, no videos), so I'm going to need to split it up onto multiple drives soon, I'd imagine

So you have 1.8tb of music all on one drive?
 
So you have 1.8tb of music all on one drive?
Yes, it's all on an external 2TB drive.

But wouldn't I have a bunch of albums titled "Various Artists" then?
You don't even need to do the Album Artist = "Various Artists". Just use the "Part of a compilation" checkbox.
Check out the attachment -- the Zero 7 album "The Garden" is followed immediately by the "Garden State" soundtrack. All of the soundtrack artists are displayed correctly, but in Finder, only one "album" would show up, in the "Compilations" folder.

The "Album Artist" field is more for albums where it's still primarily one artist, but some tracks have guest artists. You can set the artist on a track to "Main Artist, featuring Secondary Artist", but keep the "Album Artist" field set to just "Main Artist". It'll keep all the files in the same folder, and treat them as a unified album.

You can also use "Album Artist" to prevent same-titled albums from becoming interleaved in iTunes -- normally, if you have two albums called "Greatest Hits" and sort by Album, the tracks from those two albums will get mixed up. However, if each album has "Album Artist" set, they'll stay separate.
 

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But wouldn't I have a bunch of albums titled "Various Artists" then?
It's not the Album that contains "Various Artists", but the Album Artist field. This is appropriate for albums that have no primary artist, such as "Jukebox Hits of 1955" or "Death Proof Soundtrack" or "The British Invasion: The History Of British Rock".
 
Yes, I do. I occasionally grab iTunes music from my dad's account over local sharing, so we need to have it auto sorted. And for my 1500+ songs and growing, why not have it auto sort it?
 
Hello, trying to jump on, so I don't have to create a new post, it is related...

I chose to have itunes organize my music. Yes it created different files. And more folders/albums than I thought I had under each artist...HOWEVER, I still have many folders that obviously itunes does not recognize, such as folder names separated with underscores and such.

What is the best way to completely reorganize the entire collection? I saw Media Monkey is good but it does not run on mac. I guess I could always spend hours manually renaming the folders.

Any suggestions here?
 
I do not have this "Performing Artist / Various Artists" problem that the people rejecting iTunes's organization method have, and to be completely honest I don't fully understand it either... then again, I have zero purchased songs from the iTunes Store simply because the stuff I listen to isn't available there and I can get higher quality by ripping it myself.
 
I do I keep iTunes from putting some of my music in "compilation" folder?

For example: I have a greatest hits cd of a particular artist, but iTunes puts it in "compilations" instead of Artist/Greatest Hits

Example 2: I have a box set of Miles Davis. I've gone through and took songs from the box set to make an album. I changed the art work to the actual artwork, and the name of the album to reflect the actual album and not the name of the box set (after all, I have the box set, why buy the albums?). How do I make iTunes file this under Miles Davis/E.S.P. instead of Compilations?

This is why I manage iTunes myself. It puts things in the wrong folder.
 
I do I keep iTunes from putting some of my music in "compilation" folder?

For example: I have a greatest hits cd of a particular artist, but iTunes puts it in "compilations" instead of Artist/Greatest Hits

Example 2: I have a box set of Miles Davis. I've gone through and took songs from the box set to make an album. I changed the art work to the actual artwork, and the name of the album to reflect the actual album and not the name of the box set (after all, I have the box set, why buy the albums?). How do I make iTunes file this under Miles Davis/E.S.P. instead of Compilations?

This is why I manage iTunes myself. It puts things in the wrong folder.

Untick the box that says "Part of a compilation" in the info page (command-i)
 
Does everyone talking about wanting to organise their music themselves realise you can drag selected tracks directly from iTunes to wherever you like... ? Just asking.
 
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