The hardest thing to pull off? Is the story about an artist who writes the best story ever — or poem, or song, you get the picture — but you have to read part of that story in the narrative. And as you approach it you’re thinking, “Uh oh, there’s no way they’re going to pull this off.” How many times in your reading life do you hit the best story ever? 1 out of 50? 100? I can’t think of an example where it actually works (maybe you can?).
Anyway, most recent example: Family Feud. So much resource poured out on so slight a work. The backward storytelling thing was great. But the verses were… not the best story ever.
(Update: Thinking more about this, I’ve decided that Family Feud maybe doesn’t fit the “best story in a story” trope, exactly. Technically it does: the rap at the end of the video is the story referred to directly and indirectly throughout the rest of the short film, which serves as the story around the story. But in reality, no one makes an explicit claim for its greatness. It’s the embarrassment of riches spent on framing that story — A-List actors, special effects, high-concept narrative, Beyoncé in couture — that suggest the viewer infer the momentousness of the final, delayed Jay-Z verses. And their (inevitable?) inability to live up to the hype put this one in the same zip code, at least, as the rest of its “best story” neighbors.)