In this paper, the author examines several social implications of Khayyam’s poetry and the reception history of the Persian sage (hakim) Omar Khayyam, who has become a personification of transgressive ideas in Persian literary history. The fascination of the author is due not only to Khayyam’s poetic genius (although he is not the author of the majority of quatrains attributed to him), but also to his problematic reception in twentieth-century Iran and how he has been connected to the notion of modernity. Both religious and secular intellectuals have tried to position Khayyam in the modern intellectual history of Iran in their own ways.