* Jack being hit in a firefight during ''Innoncence: A Broad''. When Demarco asks him if it's bad, he pulls out his hipflask, [[PocketProtector which now has a bullet hole in it and is leaking whiskey]], he replies "It's worse!"
* Some of Jack's {{Private Eye Monologue}}s are hilariously creative with [[DeadpanSnarker snark]] and FloweryInsults aplenty.
* [[FunnyBackgroundEvent Wank: Free with drink.]]
* Jack confronts a group of hobos in the park with the intent of asking them a few questions. One of them is ''a drokking pirate'', complete with cutlass.
--> '''Pirate Hobo:''' Aar! Filthy swab! Have him walk the mizzenfuttock!