I like GMail. I make heavy use of labels, but mine are by subject. So for social networking sites like Twitter and Facebook, I used Social::Twitter and Social::Facebook. I also use priority label like *Answer for things I need to answer and *TODO for things I need to complete. I like your idea of using a separate email address for each service I signup for. I may give that a go.
Since you mention it. I'd start with watching the original Star Wars trilogy. Star Trek movies- although if you had to pick one then watch Star Trek II "The Wrath of Khan". "Tron" and "War Games" will also help with your geek cred.
From a wider cultural perspective, watch these: * Breakfast Club * Sixteen Candles * Ferris Buellers Day Off * Godfather I, II, III * Back to the Future I, II, III * Goonies * Stand By Me * Real Genius * Wayne's World * Austin Powers I, II * Office Space * High Fidelity * Singles * Spinal Tap * Almost Famous