This chapter investigates Kant’s empirical anthropological reflections as the setting for his transcendental philosophy and sketches of freedom. According to Kant, we are all empirical, embodied beings and the clash between our empirical selves and our noumenal ones are a source, for him, of both wry and witty observation as well as acute critical reflection that produces positive possibilities. It gives depth to being ‘human all too human’. I term Kant’s observation of our very human condition, ‘Shakespearean’. Kant begins his anthropological investigations precisely here – with our phenomenal existence in its full range. The faculty of the imagination, though, is the ‘wild card’ rather than the inclinations and the passions. Kant explores the imagination’s power in the Anthropology Mrongovius in ways that become more complex, differentiated and also geared more explicitly to his basic thesis of Enlightenment – to be mature and to use one’s own understanding or reason. There are significant unfinished insights that occur in Kant’s ruminations on the imagination here that overflow into his work, especially into the Critique of Pure Reason.