Social scientists have long studied the effects of cities on human wellbeing and happiness. This article demonstrates that people in cities are less happy, confirming a long-standing argument in the literature. But it had not yet been tested whether it is urbanism that negatively affects happiness, or if urban problems such as crime and poverty are to blame. Wirth posited that urbanism itself led to negative effects, but Fischer noted the necessity of empirical tests of Wirth’s ideas. This study uses a happiness measure to provide a new look at the old question of urban unhappiness. Using the Behavioral Risk Factor Surveillance System from the US Centers for Disease Control and Prevention, we aim to untangle the effects of the city itself and urban problems on happiness in the USA. We find that the core characteristics of urban life (in particular size and density) contribute to urban unhappiness, controlling for urban problems. Urban unhappiness persists regardless of urban characteristics.