John Skelton's writing career took place roughly between 1488 and 1528, years that straddle two centuries and, most awkwardly, two epochs. Perhaps because of that awkwardness he has been a poet marginalized in our literary histories and critical discourse until quite recently. This overview essay suggests that to re-engage Skelton is to test alternative literary histories that think beyond the fifteenth century as a merely transitional moment and that put into play methodologies flexible enough to accommodate inter-related notions of aesthetics and context. This essay traces Skelton's critical tradition as a series of perspectives on the poet's own nimble engagements with form and history. The first section follows the story of formalist and historicist approaches to Skelton working in tension up until the last part of the twentieth century. The second section explores the interventions of the new Skelton scholars. The third and final sections speculate briefly about fresh directions in Skelton scholarship, noticing that many of the themes and questions raised around Skelton over the past century remain open for more extensive development.