I doubt there’s enough interest in this to induce Plex to add a new menu item for it, but until they do, you can actually do this yourself, by following TeknoJunky’s tip for creating a random-sorted playlist).
If you want all of your movies in this list, instead of the filters suggested in the tip, just use “Year is greater than 1800” (or any other filter you can imagine that includes all your movies). The key for randomness is in the instruction for editing the ‘sort’ parameter in the URL.
Every time you open or refresh this playlist, on any device, you will see all your movies in a different randomized order.
