This study argues that the short lyrical poems of the pilgrimage journey between Iraq and the Hijaz by the Buyid period Baghdadi Alid scholar, theologian, political figure, and, above all, poet al-Sharif al-Radi (d. 1015 CE) play a pivotal role in the development of Arab lyricism from the classical to post-classical period. Celebrated in the Arab world, this body of elegiac lyric poems has received virtually no literary critical or historical attention in the West. I first attempt to trace the literary roots of these poems to the short lyric ghazals of the Umayyad period. In this sense, al-Radi’s lyrics, I argue, exhibit a striking double influence: they combine the heightened eroticism of the sexually explicit and consummated Umari ghazal, that is, of Umar ibn Abu Rabi’a (d. 712/719 CE), which feature the eroticization of the Ḥajj, with the erotic frustration of the chaste ‘platonic’ Udhri love lyric, of the Banu Udhra, such as Qays (Majnun) Layla (7th c. CE), Jamil Bouthayna (d. 701 CE). I then explore the metaphorical-political dimension of these two types of Umayyad ghazal and posit that al-Radi’s lyrics of erotic frustration and loss ultimately express, not merely personal and universal human emotions of lost love and departed loved ones, but also frustrated Alid political ambitions. The third section of the paper turns to the extensive and explicit influence of the Hijaziyyat on two dominant forms of post-classical poetry: first, on Sufi ghazal, such as the poetry of Ibn al-Farid (d. 1234 CE) and Ibn Arabi (d. 1240 CE), in which poems of frustrated erotic desire are taken to be expressions of longing for union with the Divine; and second, what is termed ‘nasib nabawi’, that is, the opening prelude of praise poems to the Prophet Muhammad, as in the celebrated Burdah of al-Busiri (d. ca. 1295). A close comparison of examples reveals that, although literary historians have regularly commented on influence of Udhri and Umayyad ghazal on Sufi love lyric, they have failed to observe the intimate similarities in tropes, diction, and even contrafactions (explicit imitation of a poem in the same rhyme, meter, and themes) that reveal the direct influence of al-Radi’s Hijaziyyat. The paper concludes by tracing the transitions in the metaphorical dimension of the poetics of loss, from the erotic to the political to the mystical. It concludes reaffirming the centrality of al-Radi’s Hijaziyyat in this lyrical historical development.