Even though the relationship between text and image in Timurid (1370–1507) and Safavid (1501–1722) illustrated manuscripts have been explored for the past several decades, the connection between painting and poetry in the single-page folios composed in the sixteenth and seventeenth centuries has mostly been unquestioned. This thesis examines the relationship between text and image in single-page compositions that were produced in the Safavid era. The folios in this study all have been constructed with cut-out calligraphic fragments of poetry pasted in a frame around a central panel of a figural painting or drawing. The genre of the idealised figure studies that occupy the central panels of these pages flourished in the Safavid period. The presence of such single-pages of painting alone, as well as folios with compositions of text and image, attest to a market that distinguished between the two art forms. Through a close reading of the poetry, this research argues for a careful and deliberate selection process of the verses used to convey a message unified by the visual and textual vocabulary. The thesis aims to demonstrate the different kinds of text-image relationships that could occur when the compilers attached calligraphy next to figural imagery. In order to determine where the art originated and developed, this thesis reviews the new conventions in page layout and bookmaking techniques applied to anthologies at the turn of the sixteenth century in Timurid Herat and suggests these acted as a catalyst for creating single-page compositions. The case studies presented here will demonstrate that the combination of word and image in these compositions is neither random nor arbitrary nor purely decorative, but is guided by deliberate choices, which provoke us and their original audience to decipher their meanings.