But if one simply wants a fast random 25 files to quickly listen to for a bit, no easy way. Sorry folks.
-nkormanik
Plex has something called Smart Playlists. You could create one to grab 25 tracks at random from your library and it will randomize it each time you select the playlist.
Similarly, you could create a Smart Playlist that matches the artist "Elton John" and limit it to 50 tracks and select them randomly and it will do that. I don't have any tracks by Elton John in my library, but I just did one for Radiohead as an example.
The only thing not shown in that screenshot is that it is grabbing them randomly. For some reason when you've selected to filter them by tracks it doesn't allow you to set how you order them. But if you set it to order them randomly while artist or album is still selected, then filter by tracks, it will keep the random part.