We examine the evolution of taxi regulation in North America, providing a history of North American taxi regulation. We study the current structure of taxi regulation by generally looking at regulations in North America and specifically looking at regulation in New York City, the Boston metropolitan area, and Los Angeles. We discuss theoretical justifications for these regulations. By examining how the taxi industry differs from other industries, we explain the prevalence of price and quantity regulations, and why the industry remains heavily regulated despite numerous attempts at deregulation. We discuss the cost of current regulations and how emerging technologies may face similar regulatory challenges but may also offer new opportunities.