Hackers is a movie that I thought was terrible when it came out (even as a youngster!), but now seems like a wonderful 90s period piece. It snapshots the whole hacker/raver/"burner" techno-counterculture axis of the 1990s really well, and the schmaltz and cheeze is actually pretty clever and entertaining. It sort of makes fun of itself in an also very 'period' way.

I sort of like movies that start bad and then age well.

Sneakers is also incredible. It's far more objectively cinematically good than Hackers, and it snapshots a slightly earlier era in hackerdom. Sneakers is about the time immediately before Hackers, basically before the youngsters flooded in and started hacking web apps and doing 'E'.