I can't figure out a way to get iTunes to create a playlist where every song in the list is a different unique artist, and no artists or songs are repeated. Is this possible?
(using iTunes 10, 64-bit, Windows 7)
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Through iTunes, what you are asking is not possible. However, I thought that it should be possible, and fairly easy to do through a plugin or interface to itunes,
So I did what I promised!
It's not a true iTunes plugin, as I couldn't find any real sdk or information on writing them, but its a small WPF that interfaces with iTunes through COM. I'm working on refining it and I hope to have it up on SourceForge soon.
This is done through a COM library provided by iTunes which works in .NET. Information about the library can be found here.
On windows, it might be possible through the iTunes COM interface. I never tried it, but here is an example
Based on the logic capabilities with smart playlists, to answer your question: No, this is not possible.
The logic works like this:
I can't find one, and I'm not sure if its possible - but this SHOULD be able to be accomplished through an iTunes plugin.
So in short, no, it is not currently possible.
It's too bad you're not running OSX, or you could use an AppleScript like this one
If you're so inclined, perhaps you can code up something reading the script code referenced and using akurtser's suggestion to try the COM interface to iTunes?
Here's Doug's Script's windows resources for similar options for Windows iTunes users.