This article firstly addresses the methodological challenge in drawing on imaginative literature as a source in understanding bullying. This is followed by a general survey of the profile of bullying in literature. Two key insights from literary accounts of bullying are then explored, namely, its cyclical nature and its roots in childhood. Charlottte Brontë's "Jane Eyre" is offered as an extended case-study in how a family enables the shaping of a bully. The next section deals with bullying in the school context with detailed reference to the works of James Joyce and Roddy Doyle. Attention is drawn throughout the essay, where relevant, to the class, race, and gender dimensions of bullying. The conclusion affirms the consistency between the insights from imaginative literature and the findings of empirical research on the nature of bullying.