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The Simpsons is the greatest show of all-time. People often debate the best episode of the show, or the best season. What about something in between those two things? Namely, what is the best five-episode run in the history of The Simpsons?
Obviously, we need to focus on the heyday of the show, somewhere between season three and season nine. In theory, this five-episode stretch could be split over two seasons. What tends to be the issue there, though, is that “Treehouse of Horror” episodes fall early in the season, what with the traditional TV season (and the heyday of The Simpsons was fully in the traditional TV era) starting in September. There are good “Treehouse of Horror” episodes, but for one to be included in the best five-episode run ever, you’d have to be talking about four great episodes around it.
Seasons six and seven end and begin, respectively, with “Who Shot Mr. Burns?” episodes. Again, quite good, but not all time. Ultimately, we found a run that is within a season. That season would be the eighth. We are of the mind that “The Itchy & Scratchy & Poochie Show” is the best episode in Simpsons history. It’s followed by “Homer’s Phobia” and “Brother from Another Series.” Those are two distinct episodes, and both classic episodes. That is a fantastic three-episode run. How to build around it?
“My Sister, My Sitter” is the episode after “Brother from Another Series.” Now, that one is followed by the excellent “Homer vs. the 18th Amendment.” Before “Itchy & Scratchy & Poochie” is the Sherry Bobbins episode and “Mountain of Madness.” Both are quite good, but do we include a musical episode in the run? The Beer Baron episode is just such a standout. Going that way gives us four great episodes, including the best episode, and also an episode that is still quite good.
Our choice for the best five-episode run in the history of The Simpsons:
“The Itchy & Scratchy & Poochie Show”
“Homer’s Phobia”
“Brother from Another Series”
“My Sister, My Sitter”
“Homer vs. the 18th Amendment”
