Impy, is this gonna be a monthly column? lol, anyway...
DUDE, I thought I was the only person who'd ever seen Boiler Room. It's suprising that the movie isn't popular considering it's good and included both Vin Diesel and Ben Affleck. Anything with Ed Norton in it is also an excellent choice. Have you seen 25th Hour yet?
Good list, but you included the wrong version of Romeo and Juliet. This is the one you mean't to reference We watched 3 versions in English class, the Leo DiCaprio version is the least true to Shakespeare. And even though the one I recommend is rated PG, Juliet's boobies are clearly visible throughout the whole movie. Did they have push-up bras back then? It's also the most true version. A point could be argued for yours since the soundtrack is quite good and Baz Luhrman is an excellent director.
Now I recommend:

Oliver Stone

Cheers! [cheers]

Almost forgot: MiniDisc
and Cats(Household Pets)

[Ok, I thought about editing this after realizing how stupid it is, but I'll keep it this way for entertainment purposes...]