I try not to make too many jokes on HN. They have to be very clearly funny and/or very spot-on to survive HN's this-isn't-reddit ethos, which seems to be pretty strictly enforced.
If you want to get flagged, the best way to do that is to make an irrefutable strong argument that ruffles political or economic feathers of a popular ideology on HN. There's nothing that enrages people here more than an unpopular but sound argumen they don't like, so they flag it to make it go away. If they can quickly disprove you or make you to look an idiot, they'll downvote rather than flag so that everyone can see their moral or intellectual superiority in the full thread.
I downvote jokes even if they are funny, and it is (partly) the "HN-isn't-reddit" methos. Reddit has so much noise-to-signal that it's not particularly valuable. It's like junkfood.
HN is better because every comment (per the official rules) is supposed to be substantial. Jokes that are funny but not satirical or insightful aren't substantial in my opinion.
(I should also say that I often find reddit to be hilarious, but that's not what I'm looking for when I come here.)