This chapter looks at several historical examples of apocalyptic radicalism in relation to apocalyptic literature, including the trial of Anne Hutchinson in New England in 1637 and Gerrard Winstanley’s interpretation of Daniel 7. Other examples include apocalypticism in the English Revolution involving Mary Cary, Anna Trapnel, and Winstanley. The chapter also focuses on Joachim of Fiore, one of the most significant figures in the history of apocalypticism; Girolamo Savonarola, a Dominican preacher, Sandro Botticelli, an early Renaissance painter; German theologian Thomas Müntzer; Joanna Southcott, Richard Brothers, and William Blake. Finally, it considers the apostle Paul in relation to apocalypticism and radical theology in recent theology and philosophy.