These are the opposite of Ways Jokes – jokes where explicating them only makes them funnier. The Simpsons is the diamond standard for this kind of thing, and my all-time favourite example is Skinner’s monologue on Mad Magazine in “Pin Pals”. It’s one of the most excellently crafted jokes I’ve ever seen in any comedy show; the basic joke that you expect Skinner to describe a traumatic event only for him to veer away into obsessing over a food, and everything in the monologue is geared to making that revelation as funny as possible, right up to putting a second joke right in the middle of the whole thing! I think the reason it works is because it heavily depends on Skinner’s character, making it very easy to imagine how the things he’s describing played out; part of the reason “Even though I didn’t quite understand it” makes me laugh so hard is because he doesn’t realise how he comes off here, and one can imagine not only his fellow soldiers’ immediate reaction but the overall relationship he must have had with them. Once we get to the punchline, we can also imagine Skinner travelling across America, methodically searching through Vietnamese restaurants for his mythical stew and getting increasingly fussy and pedantic about it. And to top it all off, that stew actually sounds really tasty!
What are your favourite examples of jokes that get funnier the longer you think about them?