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.
F.B.D.O was one of the top teen comedy movies for years. Even if it's not as laugh out loud funny now in comparison to other movies, I've got a soft spot for it.
but a comment about Rushmore: I thought the moive was great for the first half and then just petered off and wasted tons of opportunity. anybody else get this feeling? I've only seen it the one time.