I just divided mine up into three categories as part of my new 3 disc package (yay!).
1. FILMS (current e.g. Man On Wire, Babel, Far North, Hunger)
Basically English language movies that are worth watching of any genre.
2. ENTERTAINMENT (e.g. Spiderman 3, Cold Mountain, Wall-E etc)
Stupid watchable stuff / trad Hollywood stuff.
3. WORLD / CLASSIC (e.g. Festen, Persepolis, Hitchcock stuff, Godard stuff)
Older b/w movies of any description, world cinema stuff, foreign language movies.
I have done this because sometimes you want something "easy" and you have like three Ingmar Bergman movies, and sometimes you want something to get your teeth into and have just superhero stuff or whatever. This way I have one disc from each list all the time.
So - gimme a couple of recommendations for each? And I'll go check them out.
Note: no Jack Black. No Wes Anderson. I have seen most properly obvious stuff like Psycho and Fargo and Batman and shit.