Playing Chess is a film about the inevitability of change and how we deal with those changes. When Charles's sister, Liz, goes missing he sets out to find her. It's Liz's birthday, and Charles wants to make her their annual dinner in hopes of keeping the tradition going. Through the course of his search, Charles encounters a few strange characters, including a man looking for a quarter, two half naked jazz dancers, and some unexpected dinner guests. After upside down visions, angry old men, and some chess playing, Charles finds he must learn to accept change, and that jazz consists of more than just Duke Ellington.