So a fictional setting has, as a plot point, something that is supposed to be very funny. The other characters treat this joke or show within a show as the funniest thing they have ever heard. The problem is, due to Sturgeon's Law, few writers can actually write a joke that funny, and even a competent writer will have difficulty living up to the hype the characters give it. As a result, the joke just isn't that funny, and can become cringeworthy much more easily because the show is presenting it as the pinnacle of humor. This is one of the cases where Take Our Word for It would have been a better way to present the story element.