On the New Yorker cover (to which I'd rather not link):
I won't do the offended two-step here, because I'm no good at it. But really, what's most obnoxious about this image isn't in the image itself but in the vibe of superiority. "We," the sophisticates reading the NYer, are so much better than "them," the trogs still reading email fwds at all (let alone ones so coarse as to include sublimated racism!) that our mockery of their ignorance will go right over their heads. That they will miss the point will only validate what we knew all along: we are so great! Too great for them to ever understand! Persuasion would be pointless! When they use this cover as further "evidence" supportive of their hatefulness, well, at least we'll be able to smugly sneer over it! Once again, our superiority will be affirmed! In fact, that sneering is an end unto itself, is it not? It keeps us warm at night and nourishes our children, body and soul!
Satire, particularly political satire, works best from a position of morality, not pointed amorality. Not self-absorbed and thoughtless arrogance. That's the real issue here. Thoughtless irony isn't irony- its just an excuse to say what you don't have the courage to say straight. Truth via untruth is a legitimate tool of artistic expression, but the danger is the way it slides so seductively into self-congratulation. A good satirist polices himself first. He holds himself to a higher standard than this--or at least his editors usually do.