I have an I-Tunes dilemma. After adding much of favorite music to I-Tunes I started creating playlists. I have one for Steely Dan and one for Todd Rundgren. The Steely Dan list includes songs by Donald Fagen, lead singer for Steely Dan, his solo work. The Todd Rundgren does not include songs by The Cars even though he is now their lead singer. He was not their lead singer when The Cars stuff was recorded. This was all fairly clear to me.
Now the problem: I have a CD by Michael McDonald. I have music in my library by the Doobie Brothers, he used to be the lead singer. Do I create a playlist for Michael McDonald and include the Doobies or do I create a playlist for the Doobies and include Michael? Are these things the same in any way? He's singing Motown, not Doobie's stuff at all.
These are the questions that plague men's souls.
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Of course this dilemma of who to include where will boil down to individual choice. If you associate X with group Y, then go for it. In your examples, however, there would be no way I'd put TR with The Cars. (I think "Newtopia" will probably be a relatively short experiment. I would, however, welcome an album of all new stuff if TR and the old Car guys decided to write one. But I digress...)
In your Doobie Bros example, Michael McDonald was lead singer much later in their recording history. His distinctive vocals took the Doobies in more of a jazz direction. If I were creating a MM playlist, I would include his work with the Doobies. (BTW, MM also sang some back up vocals on Aja by Steely Dan.)
These grouping and playlist issues also "plague men's souls" when it comes to alphabetization of the collection. Do I put Pete Townshend's solo stuff with The Who? Do I put Utopia with Rundgren? If you can find it when you want to hear it, then that is where you should file it.
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