This article aims at revisiting recent scholarship on the Ottoman painter and archaeologist Osman Hamdi Bey (1842–1910) and proposes a critical reassessment of the way in which some of his major paintings have been analyzed. The central argument is that studies of his oeuvre have relied mostly on interpretation, while failing to exhaust the explanatory potential of still partly untapped sources. In an effort to redress this imbalance, a number of issues that are likely to contribute to a better understanding of the artist’s works are examined. Among these, the seemingly simple and straightforward matter of his paintings’ names reveals a surprising number of misnomers that attest to the combined effect of insufficient documentation and teleological interpretation. Two such blatant errors, namely the so-called Tortoise Charmer (1906) and Mihrab (1901), are studied in detail to illustrate this point and propose a critical reinterpretation of the nature, context, and meaning of these two iconic works. More generally, the article addresses the issue of audiences and of reception in order to challenge some of the claims made to this day regarding the artist’s intent, and concludes by proposing a more systematic treatment of this oeuvre, one that may allow for less speculative interpretations.