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You can watch Hatley High (2003) for free on Fawesome.

The Canadian teen comedy Hatley High sends up high school sports rituals by placing a most unlikely competitive game at the center of its story: that of chess. Tommy (Nicholas Wright) is a new arrival in his parents' hometown of Hatley, whose mother recently died. He discovers, after the fact, that his mom was once a chess pro and thus a legend in the community. Tommy's chess-fixated peers accept him almost instantly, inferring that he must have inherited his dear mother's skills, but in time Tommy carves out a niche for himself independently of his mom's legacy, and strikes up an enduring romance with Hyacinthe (Rachelle Lefevre) a "chess cheerleader." Two fictional British filmmakers "frame" the tale by filming it for a documentary that they are producing, and thus provide witty, ongoing narration.