Hey Arnold!
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Suggested correction: Other than the few episodes where a specific time of year is taking place; these episodes are not meant to be taken to be shown in chronological order. Just roughly in the same 4th grade school year.

Best Man / Cool Party - S3-E12

Other mistake: In the scene where Arnold meets the gang in the alley way, they give ideas to crash Rhonda's party. When Curly tells his idea to go to the zoo and free all the animals and there are shots of the gang looking at him confused,in two of the scenes, you'll notice that when Stinky and someone else looks at him, the background is at the school, not the alley.

The Aptitude Test / Oskar Gets a Job - S3-E9

Continuity mistake: In "Oscar Gets a Job", Oscar goes around asking people for money. When he talks to Ernie, you can see that there is a phone and a light to the right of the door. When Arnold confronts Oscar in the hall, you can see Ernie's room (7). The phone has disappeared.

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Suggested correction: We don't know that definitively. Those were just the only two caught as the teacher noticed their tests were very off from who they were as students. He didn't appear to check any of the others for mix ups.

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Answer: No, he did not. He is seen getting off the bus with a suitcase, so he must have not been home for a few days so there is no way he could have known.

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