Must See:
Boondock Saints (I'm fairly certain that this is the best movie ever)
Donnie Darko (good one, Beef
k: )
The Pillow Book
Prophecy (the series)
Swingers
Liked it:
Empire Records
Go
Suicide Kings
Snatch
Oceans 11
Waste of Time:
Tank Girl
Dumb and Dumber
Half Baked
Scary Movie (any)
Kingpin
There are probably lots more movies I could add to each category, if I could just think clearly.
Also, Beef, you should definitely watch LS's Series of Unfortunate Events... it's beautiful, and generally awesome.