This chapter explores anti-utopian satire in bestselling British author Terry Pratchett’s Discworld series. Like the anti-chivalric satire of Cervantes, Shakespeare, and Voltaire, the Discworld books celebrate pragmatism and local knowledge rather than political ideals. The Discworld is alive with vivid utopian impulses, however, the chapter argues that they frequently lack concrete detail. Pratchett is more concerned with constructing a colourful world of humour, heroism, and villainy. The Ankh-Morpork books reflect on the processes of historical change, accelerating a medieval city-state into liberal industrial modernity via an array of fantastically estranged forms. The city itself, however, fails to actualise into a utopian vision of the future. Rather, Pratchett’s fantasy series articulates a deep suspicion of the kind of political radicalism often associated with utopian thinking. Through a close reading of two books in the series, Night Watch (2002) and Making Money (2007), the chapter considers how Pratchett’s fantasy world laments structural violence whilst lampooning utopian remedies to such violence, such as democratic elections, trade unions, industrial action, or new kinds of post-capitalist value.