The coffee house paintings, which were created by uneducated people and based on imagination during the Qajar era, helped the public visualize epic, national, and religious stories and traditions. From the founders of this style of Iranian painting, we can mention Hossein Qoller Aghasi, who depicted the narrative of Rostam and Sohrab’s tragic story, a sad story of the father and son’s confrontation and the son’s death by the father, based on the element of fantasy and his mental imagery. The current research is based on rereading the painting related to this narrative by Hossein Qollar Agassi from Gadamer’s hermeneutic perspective. Hence, this work is read by the six parts of Gadamer’s approach, namely social and historical context, common language, dialogue, prejudice, and fusion of horizons. This research is descriptive-analytical by nature and has a qualitative approach in terms of its fundamental goal. The information and data required for this study were gathered from library sources and documents. The research answers the question of how to read and interpret the tragic painting of the death of Sohrab by Hossein Qollar Agassi through a hermeneutic perspective. By examining the mentioned painting with Gadamer’s approach, it was observed that the desired factors of Gadamer’s approach indicate the structure of the work. Hossein Qollar Agassi engages in a conversation, aware of his limited knowledge but drawing on his experimental grasp of traditional Iranian art and the common Persian language. He weaves together his biases shaped by the era he lives in, referencing Ferdowsi’s poetry and Iranian painting. By interpreting these influences through his perspective, influenced by the Pahlavi era and popular constitutionalism, he endeavors to bridge this gap. This endeavor results in a creation reflecting his cultural, social, and political milieu, yet simultaneously reviving a national and cultural identity of the past. The outcome is a distinctive style and approach that is emblematic of his time. Re-reading this work based on Gadamer’s philosophical hermeneutic approach helps to find the factors that make understanding easier. Therefore, hermeneutic approaches, including the mentioned approach, are a way to better understand the work or text under study.