This is yet another song in the chain of musically simple pieces of that have a far greater hold on me than they should. Part of that is the narrative: The improviser in me loves the triumph of the low-status protagonist, and high school-aged me relates to it — not to the Iron Maiden part, but to the crush from afar part.
A bigger part of it, thought, is the effect of re-contextualization. My theory of humor has a lot to do with violating expectations — but just a little bit and in a coherent way. So it’s odd to hear a group of ukelele players fronted by a female vocalist perform a piece about teenage angst — and even more so to hear “Lives on my block / Drives an Iroc” in a British accent. But it’s a farce played straight, as the Ukes never let on that they’re in on the joke. It has that in common with my favorite Monty Python sketches, like The Killer Joke, Nudge Nudge, or the Cheese Shop. They’re not completely absurd; there’s an inner logic to them that makes you think there’s a world in which they’re completely normal — it’s just that that reality is slightly adjacent to our own.