I also enjoyed Mike Judge's other film "Idiocracy". It's not explicitly a hacker film, but it's a sci-fi story about an average guy in a world of idiots, so it verges on hacker territory. It also has some examples of hilariously bad human/computer interface design.
(And if you're into cry-yourself-to-sleep-reality movies, there's also Outsourced, a recent comedy about a call center manager who must train his replacements in India. I found it surprisingly enjoyable. Its primary themes are culture clash and figuring out what's important in life, so it shares similarities with Office Space and Gung Ho.)
(And if you're into cry-yourself-to-sleep-reality movies, there's also Outsourced, a recent comedy about a call center manager who must train his replacements in India. I found it surprisingly enjoyable. Its primary themes are culture clash and figuring out what's important in life, so it shares similarities with Office Space and Gung Ho.)