When Harry Met Sally (1989)

Factual error: When Harry and Sally are driving away from the University of Chicago at the start of their road trip there is a long shot of them driving on Lake Shore Drive, but they are heading south towards the city with the lake on their left. If they were leaving the city from UofC, which is in Hyde Park, they would already be driving away from the city on Lake Shore Drive.

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Sally Albright: At least I got the apartment.
Harry Burns: That's what everyone says. But, really, what's so hard about finding an apartment? What you do is look in the obituary section. You see who died, find out where they lived, and tip the doorman. What they could do to make it easier is combine the two. You know, Mr. Kline died yesterday, leaving behind a wife, two children, and a spacious three bedroom apartment with a wood burning fireplace.

Trivia: Before Meg Ryan was cast as Sally Albright, Molly Ringwald was offered the role, but had to decline due to a busy schedule. Ringwald went on to play the part of Sally in 2004 in the stage version of the movie on London's West End.