For me it was Ghost in the Shell and Shadowrun, which was the first pen & paper RPG I played when I was in college. I always played a rigger because that was the first time that I ever thought about "hacking" something other than a computer or network as a lifestyle. Combining the cultures of "petrol heads" and "tech nerds" clicked with me.
But the first "cyberpunk" movie that made the idea of technology as a sub-culture real to me was, ironically, (and I hate to admit this) seeing "Hackers" for the first time. Certainly not as a real vision of what "cyberpunk" was, but rather an extremely over-the-top and glamorized commentary both on how non-technical people view technophiles as well as how people who ate, slept, lived, and breathed a tech-centered ethos might live. Like, my parents legit believed that's how I acted with my friends when I wasn't around them.
I grew up in the era of The Legion of Doom and the Cult of the Dead Cow, and realized that this hyperbolic version of the archetypical "console cowboys" was how a lot of people saw the younger generation of computer kids. They had graduated from the long-haired, bearded, ex-hippies toiling away in a basement somewhere into stylish (albeit very weird) tech-savvy young hacktivists that were trying to buck the system solely because someone told them they couldn't.
Then, reading Neuromancer and Snow Crash introduced the idea of a virtual world parallel (beneath? alongside?) to the physical world and that was the gravity that brought it all together.