This dissertation investigates the historical and present relationship of didactic poetry to the political thought of radical communities. Poetry from the Romantic period to the present is often seen as the valence of lyric and personal registers of thought, and its political utility is typically equated with the extent to which it resists concretized meaning and refuses interpretation. Didactic poetry is typically seen as a bastardization of these disruptive tendencies, as an attempt to comb theoretical and personal contradictions into straightforward conclusions and to similarly amalgamate diverse beings, people, and needs into neatly packaged political agendas. Romanticism is understood as a knee-jerk reaction against didactic and instructive styles of writing. Through case studies of Romantic poets writing on the margins and three contemporary authors invested in protest and urban space, I argue that in the hands of certain authors writing within and against systems of early carcerality, imperial warfare, and sexual control, didacticism becomes a means of imagining strange, intimate, and unstable political collectives that take shape through the communal mode of the didactic. As such, I argue that didacticism functions as both a kind of resistance/refusal and a means of exposing, exploring, and refuting the logics of usefulness, surveillance, and carceral instruction. It is, I claim, always balancing the threat of instruction tipping over into coercion with the importance of naming, teaching, and remembering marginal political histories. In Chapter 1, I discuss the problem of “utility” in the poems and allegories that Thomas Spence wrote for his periodical Pigs’ Meat; Lessons for the Swinish Multitude. While Spence wants his work to be instructive, he also actively resists the easy categorization of things and people as “useful” or “not useful” that appears in both conservative poetry by Hannah More and in British vagrancy laws. In Chapter 2, Anna Barbauld and John Thelwall use the didactic poem to think through the larger problem of teaching literature, with each arguing that literary education is a key tool for developing political collectives. Their approaches resist traditional models of literary education and criticism, models which, I argue, operate in tandem with carceral and imperial thinking. In Chapter 3, I consider the role of embodied instruction in Percy Shelley’s Laon and Cythna, taking up the poem’s formal motif of endurance. I show how moments of embodied instruction correspond with queer challenges to gender and sexual norms that reimagine learning as, instead of the transmission of information in service of clear futures, a form of material care that resists easy resolution into useful data. The final chapter jumps forward to discuss three contemporary poets—Sean Bonney, Wendy Trevino, and Diane di Prima—who adopt didactic poetry for their writing about riots. I claim that in contemporary poetry, didacticism creates a transparent subjectivity that can navigate and survive violent systems of policing.