This dissertation offers a comprehensive study of the life and work of Kuthayyir ibn ʿAbd al-Raḥmān, a love poet and panegyrist who died in AH 106 / 725 in his hometown of Medina, in the Hijaz. The dissertation reexamines the rise of monothematic love poetry in the pre- and early Islamic period, and offers a new perspective on the relationship between poetry and power, between early Islamic rituals (such as the performance of the Hajj) and rightful claims to rulership, and between cognate motifs in Umayyad poetry and the Qur'an. The interpretation of the life and work of Kuthayyir sets Hijazi love poetry of the first Islamic century within the historical context of political contexts and patronage programs in the period during and following the conflict known as the Second Fitna. Chapter One introduces the fundamental challenges to the study of Umayyad-era poetry, outlines the approach to the sources, and surveys Kuthayyir's life and textual corpus. Chapter Two reviews the scholarship on the emergence of love poetry in the first Islamic century, provides a reading of the akhbar frame in which Umayyad-era ghazal is presented, then provides translations and philological commentaries on four of Kuthayyir’s ghazal poems. The translations are followed by two essays studying aspects of Kuthayyir’s poetics, comprising a study of the poet's frequent references to pilgrimage (ḥajj), and a discussion of the poet's deployment of a ‘love-sick’ poetic persona that evokes parallels with prophet-narratives in the Qurʾān. Chapter Three then offers a comprehensive account of Kuthayyir’s career as a panegyric poet, tracing his successive patronage relationships, translating and interpreting his major praise poetry, and exploring thematic and tonal overlaps between the poet’s love poetry and panegyric. The dissertation makes the case that Kuthayyir's ghazal and panegyric should be read together, and that his patronage by the post-Fitna Marwanid elite must be considered central to our historical interpretation of his poetry. While his love poetry embeds the expression of individual erotic experience within the landscape of the sacred Ḥijāz, so does his praise poetry deploy the representation of the Ḥijāz and its rituals as a means for affirming Marwānid claims of authority. This interpretation of Kuthayyir’s work is contrasted to earlier interpretations of Umayyad-era ghazal poetry, which have focussed primarily on ghazal poetry as a creative manifestation of the disruption engendered by the societal shifts of the first Islamic century.