This paper discusses the impact of using the computer game SimCity™4 in student assignments to develop city and strategic plans. It is conceptualized around Lobo's (2005) critique of SimCity™ as ‘toying with the city’. Two University of Queensland urban planning classes (one undergraduate, the other postgraduate) were asked to use SimCity™4 to build simulated cities. One class was about building historical urban utopias; the other was about strategic metropolitan planning. The paper evaluates the effectiveness of this use of SimCity™4 to develop students' plan-making skills, and reports on students' assessment of whether and how the game's assumptions forced modifications away from preferred planning outcomes. The paper concludes that, whilst SimCity™4 is indeed based on ‘toying with the city’, city planning practice is increasingly using computer-based simulations (some based on GIS) to toy with future city scenarios to play with and understand the likely outcomes of planning policies. The convergence of the two ideas gives strength to the idea of using computer games like SimCity™4 in planning education.