How To Pun Your Way Past A Dragon
(This one actually happened back when 3.5 was the Next Big Thing™, so I don’t remember all of the specifics. The party was an assortment of good-aligned characters, and a young copper dragon stopped us from passing along the road it had decided to camp out on unless we either paid him a token fee or told him a joke he didn’t know. After dissuading the ranger from trying to pick a fight with him, we decide to go ahead and pay up since all parties involved good aligned. …Except for my barbarian.)
Barbarian: I could tell you the one about the broken dagger, but there’s no point to it.
Dragon: *Long steady stare, after the DM needed a couple seconds to work out the pun.*
Barbarian: The one about the crossbow might be worth a shot…
(The whole party groans, IC and OOC. The dragon and DM both facepalm and just point down the road.)