The proper way to organise non-album tracks

I have hundreds of different tracks that are not related to any album. How should I tag and name them?

Determine the single or the album release where they originate from. Then use this as the “album” which you use in the meta tags and the folder structure.

Plex cannot handle single tracks.

Plex is unfortunately completely album-centric. There’s two ways to make single tracks work:

  • put each individual song in its own folder and give it an album name, (name of the single, or an album it was on) (see @OttoKerner 's helpful suggestion above)
  • put them together in a folder and tag them all with the same album name (eg, “Various Singles”), with track numbers and with album artist “Various Artists”

The first option is the most work, and will clutter your library with loads of 1-song “albums”, but things like search will work. The second option basically creates a new compilation album, which looks tidier in the albums list, but comes with the downside of Plex’s problematic handling of compilations (for example, broken search, tracks won’t get played in Radio).

Unfortunately, my issue is not with single tracks (which I was able to tag to their own folders), but with compilation albums. I have a lot of “best of the 80s” type albums with their own artwork and album names. But, they do not have a single album artist. All of these albums are in a “various artists” folder on my pc. Library Radio completely ignores them, which sucks.

Plex has no support for more than one artist per album. Therefore it can only put samplers into a Various Artists “artist”.
And yes, this radio behaviour is an unfortunate side effect of Plex’s “album-centricism”.

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