This article investigates the artistic milieu of the Qajar dynasty through a critical analysis of the distinctive and sophisticated style of Mahmud Khan Malek al-Shuʿarā (1813–93), contextualizing his work alongside that of his contemporaries, with particular emphasis on Kamal al-Mulk (1859–1940), the most renowned painter of the period. Through close analysis of selected paintings, this study reveals the layered complexity of Mahmud Khan’s visual language and underscores the broader interplay between Qajar art and European artistic traditions. Although this inquiry does not seek to provide a reading of modern Iranian art, it contends that Mahmud Khan’s oeuvre warrants serious critical attention—especially within non–Persian language scholarship—as a pivotal yet overlooked juncture in Iranian art history and a missed opportunity for articulating a meaningful continuum between Iran’s classical aesthetic heritage and its modern visual expression.