Ferris Bueller hasn't held up very well. It was great when it came out. It was great a few years later. Now it's...not. It's not bad, it just seems silly now, instead of funny. Also, the parade scene is ridiculous...and not in a good way. Although recent events have made all of the scenes with the principle funnier in retrospect. Anyway, Rushmore isn't great either, but Bill Murray is, so it gets my vote.