This chapter shows how Homer’s brief presentation of Bellerophon’s solitude proved a fecund source for imagining loneliness both as privation and as resource from Homer to early modernity, in ways that only a thorough study of the classical and late antique archive can show. This chapter’s demonstration proceeds in two stages. First, it shows how Homer’s poems formulated the problem of Bellerophon’s solitude, in ways that generated a complex nexus of phrases, forms, and figures from the time of Homer down to the time of the Church Fathers. Second, it shows how the resulting Bellerophontic archive informs some of the best-known works of early modern literature, with brief deep-dives revealing different faces of this multifaceted figure, from Petrarch’s Ciceronian Bellerophon of lovelorn loss, Ronsard’s hubristic Bellerophon of poetic flight, Spenser’s adoption of Bellerophon’s lonely landscape of Bellerophon for his Christian knight, Shakespeare’s subtle and cerebral Bellerophon, and Milton’s daring integration of tradition for his audacious middle flight. This chapter thus represents a contribution to the study of loneliness from antiquity to early modernity (and of their interconnectedness), as well as an experiment in classical reception and the generative figures of poetics.