Look to Hackers (1995) for an proxy of how well hacker culture was understood at the time. Pretty sure the sports in Space Jam (1996) got a more accurate representation than hacking got in Hackers.
The curious thing about Hackers is that, while the technical side of hacking was obviously not even wrong, the culture and ethos got a much better exposure. I mean, it actually had the Hacker Manifesto read out loud:
I would even argue the technical side was better than most modern movies/tv shows (not counting mr robot). Anything looks realistic compared to ncis style 2 people 1 keyboard, lets unplug the monitor when things get hairy.
