Tales of artificially animated characters, alternatively known as “it-tales”, are among the more interesting stories written for young children. Although the psychosocial attributes of such characters are as timeless as those found in animal and human characters, they are especially interesting historically since they are a product of the state of technology extant at the time the story was written or in which the story events are located. Thus they reflect both the technology of the characters and the attitude toward such technology, both those of the reader or child and of the caregiver who transmits such tales to the child. The story of Tootle is described and discussed as an example of the steam-engine tales that were especially popular in the early to middle part of the twentieth century, and analyzed in the light of the author’s personal experience, prevailing gender role stereotypes, dynamics of heroic characters, potential impact of such stories on children’s creativity and relevant pedagogical viewpoints such as authoritarian vs. learner-initiated approaches to teaching. Critical approaches based on ideological (especially Marxist) and Jungian perspectives are also discussed. Comparisons are made between Tootle and tales of other steam-engine and similar characters. Potentially negative aspects of the Tootle story are elaborated and a hypothetical alternative ending to the Tootle story is offered.