Random Video Playback in Plex!
Hey, it’s me from 12 years after this post was written: I don’t think any of the advice below this part is still relevant. I’m 90% sure all you have to do now is go into the show page, click the dots and choose SHUFFLE.
I can’t provide any tech support for your Plex setup, but I wish you the very best in your adventures.
Post from November 2011:
Long have I sought the solution to making random play or shuffle mode for video a reality in Plex. Plex is great, for organizing and watching your media, especially if you know what you want to watch, but for some shows, like, let's say, The Simpsons, or MST3K - shows with a lot of episodes and not much continuity - what I really want is to watch them the way we watched them back in the day - at the whim of the syndication's semi-random selection. I don't care WHAT episode it is, but if you make me pick I will spend more than 22 minutes sifting through the options.
So: There used to be a trick, you could make a music share, load it with tv, and switch it over to a video share, but the music properties would persist, allowing a 'random play' option at the main menu level. An inelegant tool for a less civilized age.
Today: for OSX users of the laika build of Plex, navigate to ~/library/application support/plex/userdata/guisettings.xml (for pre-laika, guisettings.xml is a level higher. For other OSes, look around for yourself; I haven't investigated.)
Open this file in textedit. Find <settings><myvideos><playlist> and change <shuffle>false</shuffle> to <shuffle>true</shuffle>
Now, when you hit play, or open up the context menu and select play: random episode selection! This works everywhere. If you make a collection of sitcoms, or choose a whole show, or choose a season of a show, or choose 'all unwatched' you're going to get a random selection. Technically, when you choose a single episode of a show you're probably also getting a random selection of 1 item.
The only situation where this would not be the preferred behavior, I imagine, would be if you're used to hitting play on a show and marathoning episodes in sequence, which I've never tried to do before. Laika's got new features to make sequential viewing convenient anyway.
Posted for your convenience, since I've found very little information on this topic through my own searches.