EDITOR'S SUMMARYIn a search for classic works on information architecture, Joyce's Ulysses and Richard Saul Wurman's The City, Form and Intent are each compared internally across different versions and considered in terms of content, context and user. Each author modified readers' experiences through changes in the content and physical form of their works. Wurman's 1963 work, a loose‐leaf collection reflecting architecture through clay models of cities, was redone in 1974 with the same content but different physical presentation. Joyce's Ulysses was marked by variations across versions, with omissions, additions and typographic errors carried inconsistently through editions, leaving the author's intended meaning ambiguous. The context of Wurman's work was the very early stage in the author's career. The context of production of Ulysses involved composition, editing, publishing, correction and republishing across multiple channels, making consideration of the totality of the editions key to understanding the information architecture of the work. Users of Wurman's original print work exalted it, while users of a 2014 spin‐off web project see it from a different perspective. Similarly, the user experience for Ulysses varies widely, depending largely on which edition is read. The analysis and internal comparison of the two works highlight the importance of both content knowledge and technical skill throughout any information architecture project. Whether they will serve as masterworks for the field remains an open question.