Following the response I got in the meta question I'm re-asking the question with new guidelines to focus it on the direction I wanted it to have originally.
The guidelines are as follows: by "programming related" I mean movies from which we can learn about stuff like the development process, or history of software/computers, or programming culture. In other words, they must be grounded in the industry. No tangential stuff.
Good entries answer as many of the following criteria as possible:
- Teach you about the history of the industry, or the development process, or teach you about important industry related topics (software patents for example)
- Are based on real life events, companies, people, practices, and they are the main focus of the movie
- After watching them, you feel like you understand or know something about the programmers' world that you didn't before (or you can see how someone could have such a response).
- You can point to it and say "this faithfully represents the industry/programmer culture at some point in time". This might be something you would show laymen to explain to them what "your people" are like and what is it that you do.
Examples for good entries include:
- Pirates of Silicon Valley- the story of how Microsoft and Apple started the industry.
- Revolution OS- The story of Linux's rise to fame, and a pretty good cover of the Free Software/Open Source world.
- Aardvark'd: 12 Weeks with Geeks- development process.
Examples for bad entries:
- Movies who's sole relevance is that they can be appreciated by programmers. The point of this question is not to be "what are some good movies" with "for a programmer" appended to it. Just because the writers got a few computer jokes right in itself doesn't make it about the industry.
- Movies where there's a computer related element, but are not about the industry. For example, 24 (the TV series). It's a product of the information age but it isn't actually about it. Another example is movies where there's a really cool programmer character, but are overall about something completely different. Likewise, The Big Bang Theory is not about physics, even though they have a cool physicist as a character.
- Science fiction, even if it draws ideas from computers. For example, the Matrix trilogy.
- Movies that you can't point to them and say: this is a faithful representation of our world (at some point in time). If you can't do that then it doesn't mirror the industry.
Keep it one entry per answer so that the voting could sort the entries out.
EDIT: of all the entries I still like Pirates of Silicon Valley the best, so I'm selecting it as the answer.