This chapter explores the ‘special relationship’ between the literary art of G.B. Smith and J.R.R. Tolkien by examining a significant shared influence: the classical tradition that shaped their imaginations from an early age. This influence can be traced in many of the images and themes central to both authors’ poetics and is also evident in the work of many other poets and writers during the tumultuous years of the First World War. The chapter begins by analysing the most overtly ‘Latinate’ poems in Smith’s collection (such as Domum redit Poeta, Ave atque vale, and others), identifying recurring classical themes and imagery. It then offers a close reading of Smith’s classical magnum opus, the long poem The Burial of Sophocles, focusing on its classical sources and its resonances with Tolkien’s early work. Finally, the chapter reveals a pattern of creative transmission between the two friends: a classical motif, initially taken up and reimagined by Smith in his distinctive style, later reappears in Tolkien’s writings—evolving, expanding, and arguably reaching its fullest expression.