So many directions to go with something like that, how about a Meeting of the Minds kind of thing where characters discuss themselves and their predicaments and converse with each other.
Put Pinky in group therapy with some of the others in there. It could be a riot or it could be an insightful workshop.
Ya, it's interesting.
The challenge, I think, is to keep the characters rooted in their comic contexts and not take them too far out of that... I think.
I'm just feeling my way with that, I'm not a 100% on it, but my instinct is that unless a character is bigger than their comic (like Batman or Superman or Snoopy or whatever), then out of context stuff might not work too well.
i.e. the comic context is the reason for the character's existence and why you'd care about them etc. They ARE
their world, not separate.
A character like Batman takes his world with him because we know him that well, but a lot of web-comic characters are orphaned without it, just a part of the mechanism of a larger machine that can't well on their own.
Webcomic characters need background info setups if they're going to be pulled from their comics.
Anyway, those two scenarios you suggest sound cool, especially because they'll be referencing their situations and backgrounds.