This chapter selectively probes ancient and modern history for the successes and pitfalls of various models of urbanization, relating experiences in Europe, the Americas, the Middle East, and Asia. The industrial revolution brought about the standardization and mechanization of cities. Concepts of the new and the phenomenon of the instant city are recurrent, and the prevalence of the erasure of heritage and sprawling development are the warning signs of Modernist history repeating itself in China. The paradox of top-down planning alongside informal, emergent, and unintended urbanization is framed not as a crisis but as an opportunity to rethink masterplanning in the twenty-first century.