This chapter tells the stories of two dialect writers divided by more than three centuries—Andrew Boorde (1490–1549) and Edwin Waugh (1817–1890)—as a way of throwing into relief the great historical and linguistic developments that allowed dialect literature to thrive between their respective lifetimes. It begins by addressing the question of whether dialect literature might hypothetically have come into being in the centuries before the birth of Boorde. It then demonstrates how factors such as migration, rising literacy rates and the relaxation of laws around provincial publishing impacted on the education and professional lives of Boorde and Waugh. I then compare two poems authored by Boorde and Waugh, respectively, and show how linguistic and literary differences between the two shed light on language change and literary historical developments occurring during this period, and how these in turn led to the flowering of the English dialect writing tradition.