I agree...I think the later it gets, the looser and funnier they are. At nearly midnight on a Pirate & Princess Party night, we were the only ones in our boat in POTC--DD the princess and DS the pirate, with obligatory eye patch. The CM asked DS, in the most casual tone, "so how'd you lose your eye?" It was hilarious.
The latest funny was at Star Wars Weekend, and it wasn't so much what was said, but DD11's reaction to it. We met (a pretty cute) Anakin and when we walked off he leaned in close to DD and said, with a raised eyebrow and in a low voice, "may the force be with you..." She let out this ridiculous giggle, like a sitcom teenage boy meeting a supermodel. It was possibly the funniest thing I've ever heard. Little crush, DD???? Ha!