In the 1950s, the Tennessee State Highway Department planned Interstate-40 segments through Overton Park in Memphis and a central city black community in Nashville. Although slow to develop, freeway revolts emerged in both cities by the mid-1960s. Citizen activists in each city battled local municipal regimes and downtown business allies, Tennessee state road engineers, and bureaucrats in several federal transportation agencies. In Memphis, the anti-freeway organization Citizens to Preserve Overton Park, led by relentless activist and park preservationist Anona Stoner, outwitted opponents for years with appeals, demands for reviews or modifications, and eventually litigation that ended up, successfully, in the U.S. Supreme Court. In Nashville, the Interstate-40 Steering Committee, a group of black professionals led by Fisk University professor Flournoy Coles, cobbled together an opposition movement at the last moment. Their legal argument that the I-40 expressway through the North Nashville black community represented racial discrimination against an entire community seemed logical in Nashville but failed in the Supreme Court. The goal of this article, then, is to reflect on the impact of the Interstates on American cities, as well as to analyze how and why one anti-freeway movement succeeded and another failed.