Sort playlist by date Aired

[OttoKerner]

With a slightly different approach, it might work for you:

Watch crossover episodes of several series in-order

Unfortunately Plex doesn’t track your progress through a playlist. With audio, there is currently no workaround for this. With TV shows and movies however, you can make it work. This relies on the watched/unwatched status which Plex stores for every video, and on ‘smart playlists’ and on the ‘Airdate’ which Plex downloads automatically for correctly matched tv show episodes… Below I will use the Arrow/Flash/Supergirl/Legends of Tomorrow ‘universe’ as an example. This is a ‘smart’ playlist, …