Well, my 2 drachmata…
I have a book with four of Aristophanes’ plays in them, at least one of which is a comedy (been a while since I read it). I forget if Cloud Cuckoo-Land was the title or one of the main subjects of this particular play, however. It had a handful of sexual innuendos, plenty of silly characters personified by birds, and other elements that would have made it funny even to our modern tastes, although there probably would have to be lots of explanation as well.
Presumably, this was the highbrow form of comedy back in the day, which leads me to conjecture that the lowbrow stuff might have been on the level of “Jackass”. Plus ça change…
As for how Socrates pronounced his own name: given that the modern Greek pronunciation is the same as the way it was pronounced in Bill & Ted, I strongly suspect it really hasn’t changed that much over ~2,500 years.
Where the hell is Maeglin when you need him?