This chapter turns to one of the most flexible and complex political effects of cynicism: its taking of distance on the politics of the nation state. It starts by re-reading the old story of cosmopolitanism’s point of origin in the claim of Diogenes of Sinope to be ‘not a citizen’ of Athens, or any other city state, but kosmopolites, a citizen of the world. It examines the difference between the classical historical literature, in the main, wary of giving Diogenes credit for advocating universal humanitarianism, and the more-and-less critical uses made of classical history by twentieth- and twenty-first-century political theorists. On that basis, the chapter traces the lines of a specifically ‘cynic cosmopolitanism’ as it finds expression within two literary writers looking to challenge the role, and the rights, of Englishness in an international frame: George Eliot (as she turns away from ‘moral realism’, at the end of her writing career, towards more experimental engagement with the form of the character sketch), and Ford Madox Ford, as he develops and revises his literary ‘Impressionism’ during and immediately after the First World War. For both, cosmopolitanism was less a moral matter than one of psychology, requiring an internal balance to be found, in one’s own mind, between idealism and a bracingly cynical realism.