I'm more of a throwback.
1. Psycho (1960). The movie that defines Hitchcock is here. The gothic darkness rises in great pitch and the unconventionalism is unsuppressed with the heroine and her fate, the aftermath, and the most unconventional villain, played to dark perfection by Anthony Perkins. The perfect horror movie.
2. Casablanca. A World war II movie that almost dissolved outright because of the constant changing hands. The movie under multiple redos had it all: dead on banter and dialogue, excellent characterization, top notch actors. Except Bergman, who looked half asleep throughout the whole thing.
3. Citizen Kane. The biopic of newspaper giant of William Randolph Hearst by Orson Welles had everything: top humor, darkness, the machinations of Kane as he ballooned to immeasure heights and the fantasy surrounding his death. A true spectule in the purest sense.
4. Serebii: a Timeless Encounter. Yes, it's a Pokemon movie but the first one to attempt cleverness, subtlety and fanboy treats unlike the previous three and the sheer attempt at such cleverness, with one but two fan favorite Legendaries, an agent of the Rocket-Dan as the villain, and we see nuance, actual nuance. This and the dub itself was done well, with all the bells and whistles and one of my favorite animated movies.
5. Sayonara. The novel of Japanese culture and Americanization in the mid 50's made quite the impression as an Air Force colonel (played nicely by Marlon Brando) who didn't care for the Japanese people befriended his subordinate who married a Japanese girl and ended up falling for the head of one of the top Japanese theaters, who also has her issues with the Americans. Both he and her fall into culture issues, job and oblignation issues and finally, end up falling in love. Truly dark and sweet, and while long, it was the perfect length. The perfect race movie. Particularly relevant with me and my recent changes of life.
Of course any movie with Sam Waterston is a gimme. But those are my choices. But that's always subject to change.