The life and work of the computer scientist Joseph Weizenbaum is a testament to the ways in which the field of artificial intelligence has engendered discontent. In his articles, public talks, and most notably in his 1976 book, Computer Power and Human Reason, Weizenbaum challenged the faith in computerized solutions and argued that the proper question was not whether computers could do certain things, but if they should. As a computer scientist speaking out against computers, Weizenbaum has often been treated as something of a lone Jeremiah howling in the wilderness. However, as this article demonstrates, such a characterization fails to properly contextualize Weizenbaum. Drawing upon his correspondence with Lewis Mumford, this article argues that Weizenbaum needs to be understood as part of a community of criticism, while also exploring how he found the role of discontented critic to be a lonely and challenging one.