Sure you can.
you can do so with filters > auto playlists.
optionally you can use collections where applicable
the general instructions are listed here, including if you want episodes in a random order, see also @ [TIP] --- how to create an autoplaylist with random sort
as to what filters you need to use, that is entirely dependant on the specifics of what you are trying to accomplish.
for dc/cw multiverse;
- plex web
- tv library > library view
- custom filter > episodes > by air date (desc, may have to click air date twice)
- show title is > whatever + wahtever + another (be sure to add all of the shows you want on the same line)
- alternatively you can use ‘show collection’ (if you have put all the shows in a collection or multiple collections)
if you want unwatched episodes only, add another filter (click the little filter to the right of the filter)
- episode played is untrue
finally, once you have the filter exactly as you want it,
- save the current url to your browser bookmark (so you can go back to it easily)
- save the filter to a playlist > click the plus with the lines and name the playlist
