“Last Exit to Springfield” – Season 4, Episode 17
When Lisa needs braces, Homer steps up to make sure the power plant’s union doesn’t let Burns revoke dental coverage. And thanks to being stupid and lucky, he’s able to convince Burns that he’s a smart negotiator and eventually leads a successful strike in a fantastic episode that features some truly classic jokes. Oh, and Lisa plays Classical Gas while Lenny jams out. It’s the kind of joke that wouldn’t happen today in the show, but back in the early, slower seasons, it fits perfectly and is still fondly remembered to this day.
