In this paper, I intend to explore the roots of Jung's psychological elaboration of the ancient notion of active imagination. The revalorisation of a creative and healing function of imagination was central throughout Jung's life and work. In the first place, it was crucial in Jung's visionary experiment known as Liber Novus [New Book]. Later, it played a primary role in the progressive adaptation of active imagination as a therapeutic tool in analytical psychology. At the same time, an increasing interest in the creative faculties of imagination was in the early decades of the twentieth century the object of a cultural, cross-disciplinary discussion which affected the intersection between psychology and terrains such as art and literature. In this paper, I aim to offer a brief survey of the way in which Jung's reflection on the nature of imagination was underpinned by the experimental lines of such cultural moment.