For centuries, musicians of all forms in Iran have suffered the indignities of low social status and, in some cases, a dubious relationship with the law. As elsewhere, street musicians have suffered more than most, but Iran’s longstanding tradition of diverse street music has, to some extent, managed to survive the various attempts of authorities to suppress it. In the early and mid-twentieth century, the Shahs of Iran’s Pahlavi dynasty sought to “modernize,” “Westernize,” and “sanitize” their country’s social and cultural practices, in part by attempting to ban street music and associated forms of street entertainment. The qualms shared by authorities and “respectable” society were based on paradoxical notions of morality and modernity. To some extent, these same attitudes persisted after Iran’s 1979 Islamic revolution and the Iran–Iraq War. While the laws around music practices after 1979 were based more explicitly on a reading of Islam, social attitudes to music and musicians remained largely bound by notions of respectability. In twenty-first-century Iran, some “traditional” and prerevolutionary street musicians still appear, but they are joined by young rock, fusion, and jazz musicians. These new street musicians’ social and legal status remains uncertain, continuing Iranian musicians’ long history of working between the cracks of a fractured society and its laws.