This is probably a pretty unusual request, but here it is anyway. I'm pretty passionate about classic cinema. Back in the Warner Brothers would release classic movies on DVD and they had this "Night at the Movies" feature, in which the film would play AFTER a news reel and a cartoon that would have come out the same year as the film, pretty much like you would expect to see in the theater.
I've got the movies, the cartoons and the newsreels, is there any way to get Plex to auto-generate a short 3 or 4 item play list based on release date from a couple of different libraries? Like if I pick a movie that came out in 1944 it'll select a news reel from 1944 from my newsreel library and a cartoon as well?