My boyfriend and I sometimes have endless discussions over which of the 100 unwatched movies we want to watch. Usually this ends in us watching an episode of a TV show instead because we can’t decide, but I do want to make progress on the unwatched movies someday too…
What we really need is an option for Plex to decide for us, a button which plays one of our unwatched movies at complete random. Or suggests 3 random movies of which we then chose one.
Would that be an option for the next release? 
My installation can already do this.
(I go to “all unwatched movies,” cover my eyes, and hold the down button for a random amount of time.)
j/k, sorry, it’s actually not a bad idea.
+1
This is something that has been requested many times and I can’t wait to see it come to fruition. Cutting the cord will be that much easier.
Neat idea, I’m not sure how to add it to the GUI though and they’d probably want to fix the shuffling bug with music before tacking what’s effectively shuffle for video. 
Reviving this from the dead. Anyone know if this got implemented?
+1
Random movie and random TV show episode are both desired. SouthParkStudios.com does the latter and it's really convenient.
+1
I was going to suggest a button called "Movie Roulette" to do such a thing, but realized it could be applied to each media section as well to play a random song, show a random photo, etc. Perhaps it could even be either section or non-section specific?
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+1 I would totally use this.
Edit: It is mostly implemented in the Android client. There is a shuffle button when viewing movies that plays a movie at random but I don't know if it takes into account watched vs unwatched.
This works strictly inside of plex/web on the chrome browser; this extension allows for random selections
Just incase anyone is wondering this has been added now into Plex its self in both the web browser and I see in android app (willing to bet its also in the iPhone and other clients) go to the movie or TV folder and at the top it will have a Shuffle button, click that and it will randomly play a movie. (Not sure if TV shuffle will pick a random tv show or a random episode of all the tv shows, hoping the 1st episode or the 1st unseen episode of a random tv show)
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