These are in no particular order

Waking Ned Devine - Hilarious Irish film about winning the lottery.
Trainspotting - Ewan McGregor. Creatively funny movie about Scotish drug addicts. This movie contains THE funniest scene that I have ever seen.
The Full Monty - Robert Carlyle. Comic British film about a town that was once booming due to a steel factory, but has recently moved out. This is a story about a few of the regular men who were laid off trying to make ends meet.
Bettlejuice - Micheal Keaton, Geena Davis, Bill Pullman. Interesting rendition about what happens in the afterlife. A childhood favorite.
Breaking Away - Dennis Christopher, Dennis Quaid, Daniel Stern. Best Screen Play 1979. From my Alma Matter! This is a great coming of age film based on a local bike race at Indiana University.
The Usual Suspects - Kevin Spacey, Best Suppoting Actor (1995??). This is an incredibly well done suspense movie. This is my all time favorite. I will say no more to prevent ruining it for anyone else.
Zero Effect - Bill Pullman, Ben Stiller. Quirky investigation mystery. I highly recommend it.
Empire Records - Liv Tyler, Renee Zellweger. Teenagers save their local record store from Corporate take over. A coming of age comedy.
She's the One - Jennifer Aniston, Cameron Diaz, John Mahoney. This is a funny story about chosing a life-long mate.