[UncleSim]

OK, I've been searching all day, and maybe I'm missing something somewhere, but here is my situation:

My wife wants to be able to play one show, and see random episodes of that one show, automatically.

For example, she wanted to watch random episodes of Looney Tunes this morning. We've used Plex for a long time, and she could just hit the shuffle button there, and get random order episodes of Looney Tunes all day.

Any way this can be done, either with LazyTV or not, or any other suggestions?

You should be able to set up LazyTV (or a clone of LazyTV if you already have one set up for another list of shows) to play Looney Tunes or whatever in random order, by selecting it under random-order shows, right below the normal show selection setting.