The seventh-century Madinan poet Hassan ibn Thabit is best known for his role as poet laureate of the Prophet Muhammad. His poetry composed in defense of Muhammad and the nascent religion of Islam has been widely studied, and it is in this context that Hassan appears in Arabic literary history. Yet, as one of the mukhadramun, a class of poets whose lives spanned the pre-Islamic and early Islamic periods, Hassan is a transitional literary figure who composed poetry in two distinct eras. This study focuses on an understudied subset of the poems attributed to Hassan: his twenty-six poems and fragments composed on the Ghassanids, a sedentary, Christian kingdom located in modern-day Syria and Jordan where Hassan served as the primary court poet prior to the rise of Islam. Relying on this body of poems and employing the methods of contextualized close reading and in-depth textual analysis, this paper argues that Hassan is a pioneer in the urbanization of Arabic poetry and a precursor to the city-dwelling poets of the later 'Abbasid caliphate. In contrast to the desert-related stock motifs and themes that dominated the poetry of his contemporaries, Hassan's verses reject the idealized portrayal of nomadic life in the desert. His compositions praise life in the cities and towns of al-Sham and detail the luxurious quality of life enjoyed by inhabitants of this region. He frequently presents a sharp dichotomy between sedentary and nomadic lifestyles and contrasts the comfort in which sedentary tribes live with the relative poverty of nomads who roam the harsh Arabian desert. Hassan's poetic lexicon also demonstrates a familiarity with an urban rather than desert landscape. By exploring the urban features of Hassan's Ghassanid poetry, this paper aims to shed light on both the urbanization of Arabic poetry and the diverse range of settings in which pre-Islamic poetry was composed.