The Watermelon Woman (Film)
If you are even remotely interested in working in/appreciating film, I beleive you need to watch Cheryl Dunye's 1996 film The Watermelon Woman. It's important for any number of reasons but additionally, it's also the first film directed by an openly lesbian Black woman.
Stories Of Your Life and Others (Book)
Ted Chiang's book Stories Of Your Life and Others is one of the most thoughtfully constructed collections of writing I've ever seen. Division by 0 is my favorite story in this collection.
The Beginner's Guide (Videogame)
The Beginner's Guide is one of the most unique games I've ever seen. I do not share things about it for fear of dampening its beauty. Buy it and play it yourself, or if you can't afford it, watch a playthrough. Thanks Davey.
Twin Peaks (TV)
David Lynch is my greatest inspiration in life and in film, and Twin Peaks is his masterwork. If you cannot find it in yourself to watch the show, at minimum engage with the pilot episode.
Ends and Odds (Plays)
Samuel Beckett is one of the strangest writers to ever live, and these are some of his strangest pieces of theatre put together in one book. Something about this one just gets me. (If you haven't also read Waiting for Godot really just one of the best things out there.)
Skinamarink (Film)
The only film to truly frighten me in all my years of living. A study in helplessness and dread. Watch with the lights off, it really is better that way.
Rosencrantz and Guildenstern Are Dead (Play)
So if Samuel Beckett is on here, it's only natural for Stoppard's masterwork to follow. Ros and Guil Are Dead is somthing really special. I hope to direct this show one day---maybe even while I'm at school.
If on a winter's night a traveller (Book)
Italio Cavlino was one cool dude, and he wrote the craziest book on the planet. True insanity mixed with brilliant prose, an appreciation for streching the limits of punctuation, and a heartwarming but impossibly tangled story.
Dungeons & Dragons/Pathfinder/Tabletop Roleplay (Games)
This is how life was meant to be lived: playing these games once a week with people you know. If you and your friends don't play these, get on it. If you don't have friends, make them to play ttrpgs with them. No exceptions.