Comedian and nightclub performer Lenny Bruce became well known in the late 1950s and early 1960s for his no-holds-barred riffs on religion, politics, and sex. Many considered him “the most radically relevant of all contemporary social satirists.” Others believed his work had no artistic value and was simply obscene. He was repeatedly arrested for violating state obscenity laws.

Bruce said, “If I get busted in New York, the freest city in the world, that will be the end of my career.” In 1964, undercover police detectives attended his performances at the Café Au Go Go in New York’s Greenwich Village. He was arrested, tried, and convicted. He appealed, but died of an overdose of morphine before the conviction was overturned.