Spoilers ahead: for the puzzle and the movies/games
This page reveals all categories and answers for this puzzle. It also discusses plot details, story endings, and other spoilers for some of the movies/games shown.
easy
Directed by Tim Burton
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medium
Starring Cate Blanchett
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hard
The film begins and ends at the same physical location
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Each film opens and ends at the same place: Xanadu in Citizen Kane, Norma Desmond's mansion in Sunset Boulevard, Dorothy's farmhouse in The Wizard of Oz, the Don's study in The Godfather. The endings land differently once you realize you've seen this room before.
tricky
Title is the name of a real city
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Each film's entire title is the name of a real city: Casablanca (Morocco), Chicago (Illinois), Munich (Germany), and Selma (Alabama). The films span different genres, eras, and continents, so the geographical fact is the last thing a player would notice.