If you have a particular style of witty observational humor that you prefer, providing the model some examples of that will help it generate better output. It's capable of generating pretty much anything if you prompt it the right way. For truly nuanced or novel things, you have to give it a nucleus of novelty and axis of nuance for it to start generating things in your desired space.

If I tell it exactly what I want to hear, where's the surprise? Is there any novelty there?