Shawshank Redemption: If you've ever "served time" at Bethel, you can't help but connect with this film. Institutionalization, mental persecution and "Andy Dufrene crossing through 500 yards of shit, came out clean on the other side. Classic, classic movie.
The Matrix (First one): Who couldn't relate to the choice that all of us as J-dubs at some point had to ponder: do I take the red pill or the blue pill (should I stay or should I go)?
Good Will Hunting: I connected with this one on the basis of me deciding whether I should attempt to reach my potential or wallow in the bureaucratic muck and waste the best years of my life. I'm Will headed out to California in search of a girl..........
Those are some of mine. What movies do you connect with that kind of capture the quandry of your J-dub years/experience?