At the unemployment office, when Larry Daley (played by Ben Stiller) speaks to Debbie he says that he felt a connection with her when he first walked into her office and with a deadpan face she quips back that she did not. Debbie is played by Ben Stiller's real-life mom, actress and comedian, Anne Meara. See more...
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Factual error: When Larry is running away from Attila the Hun into the elevator, he pushes both hall buttons (up & down). When the elevator is descending, the indicator shows him going down from the top floor. The top floor only has a down button. Also, in that type of Otis elevator, when both buttons are pushed, the up light goes out first, indicating the elevator is answering an up call. The doors would recycle to answer the down direction before the down light would go out.
Other: When Larry crosses the street, when going to the museum for the first time, the traffic light for pedestrians is red the entire time. Yet he and other pedestrians casually cross the street (he even stops for a bit) while the yellow cabs don't make any attempt at driving off (although their light should be green). Although there's a small gap between one light turning red and the other turning green, it takes close to 10 seconds while nobody appears to be in any rush.