Mamayh ar-Rumi ad-Dimasqi was one of the most significant Damascan poets in the 10th/16th century, whose verses were sung from Damascus to Yemen. Based on the current results of the ongoing edition of Mamayh's diwan (Rawdat al-mutaq wa-bahgat al-'uaq Garden of the ardent yearner and the joy of the lovers) this study discusses a selection of poems in which the poet converses with the literary past by not only using mimetic and emulative techniques (like tadmin, iqtibas, and tahmis poems) but also through the use of more modern styles, forms and topics (like 'atil verses, coffee poems, and vernacular poems). While the mimetic poems refer directly to the admired or canonized models of the past perpetuating the tradition into the poet's present, the focus of the contemporary topics in the diwan is on how the poets present is connected to the poetic and aesthetic practices of the past. With the analysis of Mamayh's poetry, the study offers evidence of the impressive literary and intellectual background of an initially Ottomanized and then 'Syrianized' (former soldier) poet, as well as his tremendous poetic creativity in melding together the old and the new in his verse.