Under the prevailing condition of uncertainty that postulates the impossibility of predicting the long-term future of the contemporary urban societies, spatial planning and design seemingly require new methodologies for an effective future perspective on the human settlements. Used to rely on forecasting as an extrapolation technique projecting no further than 15-20 years ahead in practice, the profession largely falls insufficient to suggest a forward-thinking approach, today. To transcend such settled 'short-termism' in urbanism, new futuristic methods enabling designers to come up with more articulated ideas on future forms and patterns (despite the restricting cognitive effects of complexity, and those of the actual context) are needed. In this regard, the paper revisits the idea of 'imagineering' to increase the foresight capacity of urban designers in the generation of futuristic urban scenarios in an effective manner. Based on some selected works conducted in METU Master of Urban Design Studio, Ankara, Turkey, the cognitive power of imagination and the methodical use of 'backcasting' are argued as the proper methodical framework to empower futurist design thinking in urbanism.