This 44-minute film is the debut of director Akio Jissoji, and is written by New Wave giant Nagisa Oshima. When Twilight Draws Near begins with four bored students engaging in aimless conversations in their apartment. They ponder what could be the best possible opening line to a song, to which one of them responds: "When Twilight Draws Near". Considering the movie's existential themes, it's possible that the title is a metaphor for death slowly creeping on the protagonists, but that would probably be too obvious.
The students then get the idea to play a game inspired by the accidental gas leak in their apartment. The last one to exit the room wins a small amount of money. Naturally, this delves into tense dialogues about life itself, as the two first ones to exit the room are seen as people who don't care about their lives in a stunning twist of irony.
Some parts of the film are pretty cryptic, especially the closing three minutes which just show the face of one of the students set to some classical music. However, it's a good thought-provoking film that knows its limits even though the story can be expanded and still make sense. It has that dark visual style of Jissoji's films where everything is covered in blackness and the acting is great. Very cool.