This special issue considers historical actors who have publicly tested what has been codified as illegal or cast as illicit, reflecting on how a critical and radical engagement with historical interpretation, art, and activism can confront, remake, or move beyond institutional authority. Collectively, the essays examine a range of sites where challenges to the law and prevailing social customs have taken place, whether on urban streets, in archives, or in museums and courtrooms. To explore the obstacles facing those who engage in civic activism, the essays treat such topics as homeless GLBT youth in San Francisco who protested city-mandated sidewalk clearings; Women Against Pornography, a group that strove to make Times Square safer for women without relying on state censorship; and an art installation that protested deportation raids of unauthorized immigrants undertaken in San Francisco despite a city ordinance designed to protect residents regardless of their citizenship status. One essay offers an ethnographic reading of the police archives of Guatemala to demonstrate how physical access to knowledge is crucial to rewriting state histories of criminal subversion. A forum on police museums in Argentina, Cuba, and Mexico examines how the presentation of these official histories shapes the public’s encounters with some of the most problematic manifestations of state power. An illustrated essay on illegal graffiti murals left undisturbed in a gentrifying Los Angeles neighborhood demonstrates how illicit place-claiming can be recast as edgy cultural capital by the same forces that it originally resisted.