The Princess Bride to The Big Lebowski to Spirited Away. The films whose specific gift is that they get richer on repeat viewings.
Some films are best on first viewing. The twist works once; the structure rewards your initial confusion; the surprise carries the film. Other films are designed for return. They unfold their material across multiple viewings; they reward the audience who has already met the characters; they offer different things at different ages.
This list is the second category. The films below are ones we'd be willing to watch any given Friday night, and have.
The films on this list share several structural properties. First, character: the lead characters are people you want to spend time with rather than puzzles to be solved. Second, dialogue: the films are quotable. Third, comedic register: even the dramas on this list have comic relief; tonally relentless films are rarely on rewatch lists. Fourth, runtime: most are under two hours.
The films that are not rewatchable, by contrast, tend to be those whose primary pleasure is informational — they tell you something you did not know, and once you know it, the film has delivered its content. Once and Done films can be great (we have many such films on our other lists), but they are not Friday-night choices. The rewatch films are the friends. The Once and Done films are the conversations.