Children’s literature and film is commonly assumed to be simplistic and therefore, deemed by some, unworthy of examination. Texts and films that are categorised children’s entertainment are expected to not be as complex as literature and film aimed at adults because their presumed audience is children, who are typically believed to not understand subjects and narrative structures that are considered to be too complicated. Children’s texts and films are, however, more complex than they seem. There is a notable duality within children’s texts and films that can speak to their complexity. Dualism means that two concepts or aspects are contrasted, in this case within children’s stories. In this thesis, the complex duality within children’s literature and film is examined in Alan Milne’s Winnie-the-Pooh, The House at Pooh Corner, and Marc Forster’s life-action animation film Christopher Robin. They are chosen because of their popularity and their firmly held position within the category of children’s entertainment. The objective of this study is to explore in what ways these texts and the film challenge the assumptions held about them as simplistic. The seeming simplicity is actually complex due to dual aspects that are opposed and contrasted. These contrasting aspects include characters who seem simple, but are not; toy characters who differ in function and meaning; opposing concepts of childhood and adulthood; structures and techniques that address both children and adults; and, the dual aspect of genres and modes which are significant in conveying meaning, and that also demonstrate setting as a metaphorical and symbolical device. Together these dualities reveal an inherent complexity in the chosen material and they suggest that the most pivotal duality is the contrasting aspects of childhood and adulthood.