I love Hard Eight (aka Sydney), but most people I mention it to find it a bit slow. Directed by Paul Thomas Anderson before he made Boogie Nights, it stars the great John C. Reilly as a down on his luck gambler trying to earn money for his mom's funeral. Philip B_aker Hall takes him under his wing and teaches him how to work the casinos for a little cash. Samuel L. Jackson, as always, is pretty kick ass here and Gwenyth Paltrow does an excellent job as a miserable waitress/prostitute. There's some great dialogue and character development here, but the pace of the movie irks people with short attention spans.
Does American Splendor count? Read about it everywhere, but don't know anyone who saw it. Except me. It was good. Highly recommended for a rental when you don't want to watch another sci-fi/action/adventure flick, and your girlfriend isn't making you watch the latest Meg Ryan crap.