The Wayward Cloud examines the relationship between an amateur porn star and a lonely woman. They know each other from the past and both of them are desparately seeking a connection. Will they succeed? They go about their daily lives on a calm pace which is sometimes interruped by odd musical numbers. These musical bits are charmingly off-beat when compared to the rest of the film. It is like the film's story flows back and forth between two completely different layers. There is this sort of "dualism" in the "porn" scenes too. Sometimes you can see the people behind camera in rather amusing situations, and then there are scenes where they are completely non-existent. Tsai brilliantly switches between these two "styles" to emphasize certain aspects of the content. For example, the first porn scene catches the viewer completely off-guard and it is done "professionally" with no visible cameramen, complete with costumes for both characters. The most shocking part is what actually happens during the scene - I'll leave that for you to find out.
Despite the film's cold and alienating attitude most of the time, there are truly hilarious moments. Tsai is able to include his "trademark humor" into the serious content seamlessly. For example, there is a lovely scene which uses only one shot: the shot is divided by a wall in the middle of it and we can see one main character on each side. The man tries to be nice to the woman and accepts the drink she offers to him. While she goes behind the wall, he disposes of the drink without drinking it - because it's god awful. When she comes back, he kindly gives the glass back to him, which she interprets as him wanting more. His facial expression after she fills the glass again is priceless. The same sort of composition is used later in the film for a completely another purpose, but it is certainly meant to be parallel to this scene.
The film's Taipei is under a drought which has made watermelons extremely common, to the point of them becoming a fetish. All of this can be seen as a metaphor for the "dryness" in the relationships of the characters, the lack of connection. The Wayward Cloud's watermelons are infamous among cinephiles.
Apart from the musical scenes, Tsai's form doesnt hold any exceptions in comparison to his other films. He likes to linger on carefully framed and beautiful shots which are often used for a certain purpose. Even his musical numbers follow his tradition of only using old Mandarin pop songs which surprisingly fit really well with the modern setting.
I seriously cant find any mentionable flaws from the film, and it is great as it is. It is an intriguing example of how far cinematic language can go.
Score: 10 out of 10
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