I know slavoj zizek is a fucking loser now, but his movie A Pervert's Guide to Ideology was the first piece of media that began to rub away the sheen/shellac of pretense that the world operates smoothly. It was my first time really engaging with a Marxian analysis and sitting with it. I was in high school, and it set me up to care about critical theory. From this movie, I'd read Mark Fisher's really quick book "Capitalist Realism: is there no alternative?" Fisher grounds a lot of his theory in culture/media in a very similar way to Zizek.
After that, I'd follow recommendations made by others in the thread!