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Personification has slipped in and out of fashion over the centuries. This paper looks at artistic representations of eccentric personified figures encountered by the author in archaic church settings and locates them in a historical context, looking at their antecedents and chronicled treatment, from iconoclasm to idolatry. It compares these objects with modern-day practices of active imagination. C.G. Jung encouraged his patients to draw or paint the imaginal figures they encountered in dreams or active imagination, just as he illustrated figures he encountered in Liber Novus. This paper concludes that the helping professions might benefit from an increased use of personification.