The joke here is harmless enough, if not a little bit cruel. (What did the Wilsons ever do that we should laugh at their poor money management?) No, the interesting part of this comic is Dennis himself.
First off, why the hell is he even there? Did the Wilsons invite him over to help with their financial planning? Did he sneak in because he’s interested in accounting? What’s menacing about that?
But then again… there’s something about that expression he has. His eyes look even more soul-less than usual. His eyebrows are raised expectantly… He almost seems satisfied. I might be misinterpreting this one, but it appears that he’s there to offer the Wilsons some sort of Faustian deal. “Your souls for a proper 401K” he’ll whisper. I don’t know why he wants their souls, but you have to admit, this strip is taking menacing to a whole new level.
Final verdict: Dennis the Menace might be the Antichrist