Continuity mistake: In the episode 'Lisa's Sax' (season 9, ep. 3), King Toot's music store is across the street from Moe's Tavern. However, in numerous later episodes, there are stills of Moe's Tavern that show King Toot's music store next door, not across the street as in the aforementioned episode.
Factual error: In the scene where Lisa's great great grandmother, and the slave Virgil escape to Canada, they enter Canada across a suspension bridge, which has, on the Canadian side, the Canadian Maple Leaf flag. In 1860, Canada was not yet even a country, and the flag was the Union Jack and the Canadian Ensign. The Maple Leaf was not adopted as the Canadian flag until February 15, 1965.
Factual error: During the video screening at the Teacher of the Year committee, the panel is watching the teacher who acts like Robin Williams. In the video the main judge says "Next" and pushes a button on the video control. It goes to the video that Bart Simpson sent in. How was this possible? The video control would only fast forward the video and two separate entries would not be sent in on the same tape. The committee wouldn't have spliced the footage together onto the same tape as the tapes were piled up on the desk. At the start of the scene one of the judges mentions to put in the next tape.
Continuity mistake: At Asa's funeral Burns and Grandpa both produce a key to unlock the compartment in the Hellfish monument, but even though they both take their keys out of the keyholes after turning them, all 9 keys are in place in the following shots.
Factual error: In episode 19-7: "Husbands and Knives," the cover of "World's Finest Comics" 94 is shown on the wall at the comic book store. It features Superman with a sign that says, "Gotham or Bust," and Batman gulping. The actual cover of "World's Finest Comics" 94 shows Superman being sprayed with liquid kryptonite while Batman and Robin catch sight of him.