Triumph of the Nerds is amazing. Some of Steve Jobs' best quotes come from there. It's interesting to see in historical context as well - Microsoft was still on top, and Apple was going through hard times.
I was an engineer at Netscape through the period this documentary covers and it's one of my favorite (though bittersweet) documentaries. I wasn't involved in the development side, so my involvement with most of those featured was quite limited, but . . . what a great piece. I'd also couple it with (what I'm sure has been mentioned elsewhere, but I've not read that far, yet) Revolution OS ( http://www.youtube.com/watch?v=CjaC8Pq9-V0 ).
it's a documentary about josh harris- mostly his startups after jupiter. pseudo.com, and a bunch of people living underground.
the beginning covers a bit of the early nyc scene in general as well. pretty cool movie if you take it for what it's worth. jason calacanis and fred wilson both make appearances.