Weaving together influences from philosophy, visual and sonic aesthetics, and radical political thought, this project argues that individual and collective imagination should be understood as important sites of politics-in cultural, discursive, institutional, and collectivist registers. Rather than proposing dogmatic adherence to any particular ideology, we find that imagining new possibilities, as well as the possibilities for more possibilities, is centrally important to the endeavor of seeking radical change in the contemporary capitalist/state system. By turning to the examples of two politico-aesthetic movements, the Handicraft movement of William Morris and the Hammersmith Socialist League of the 19th century and the 20th/21st century cultures of punk rock, we witness the successes and failures of attempts to intervene in political imaginaries. I focus on the anachronistic, non-capitalist mode of production of so-called 'do-it-yourself' (or D.I.Y.), I argue that such productive processes could represent such an inter-temporal rupture point of radical anachronism that I have theorized, and can therefore demonstrate the potentiality of wellsprings for the creation of new forms of politics, paradoxically contributing to the progress of inclusivity and egalitarian politics through the introduction of anachronistic performances, visuals, and music. Specifically, they reveal the surprising ways in which inter-temporal rupture through anachronistic aesthetic forms and modes of productions can not only disrupt hegemonic notions of progressive linear time, but also question the radical imperative towards production of the new. These movements hence illuminate important implications for the tactics, tensions, and most of all thought-and preconditions for thought-that underpin contemporary progressive politics (e.g. Anti-globalization, Occupy, Black Lives Matter, revolutionaries in Rojava and especially, and most contentiously and controversially the contemporary Antifa movements) by demonstrating the radical potentialities of aesthetics, space, and anachronism for the introduction of historical rupture contained within politico-aesthetic shock. These movements are deeply concerned with democratic participation and social justice, and so we can use Morris and punk as a window in to deep analysis of tactics as utilized by the aforementioned anti-capitalist and anti-fascist movements.