The mid-seventeenth century English social movement known as the Levellers was perhaps the first liberal-democratic social movement. Among their communicative strategies, to garner supporters while challenging the authorities, humor figured prominently. In this article, the nature of this levelling laughter is highlighted and juxtaposed against Puritan injunctions to mourning and objections against humor. Regarding the latter, four such objections are distinguished and elucidated: “damnable heresies”, “strange opinions”, “fearful divisions”, and “loosenesse of life and manners”. Finally, it is suggested that the Puritan repudiation of the Levellers highlights the need for social movements of democratic dissent against various aspects of the given status quo to use incongruous and relief humor to prompt reflection without relying too heavily on boorishly flouting social prohibitions for the sake of the pleasures of superiority and release. It also suggests that humor will do better in a culture already tolerant of pluralism, comfortable with a measure of non-literal ambiguity, and committed to democratic deliberation.