Poetry and humor are two distinctive methods by which words can be manipulated in order to produce an aesthetic effect. Historically, the use of laughter was present in various ways in models of poetic creation. The act of poetic sublimation in Brazilian literature used irreverence in different social and cultural contexts. Whether this sublimation was used for a scathing attack on individuals or institutions or to modernize Brazilian literature, the act encouraged the questioning of established truths. We seek to investigate these possibilities for dialogue between poetry and humor into three different episodes of Brazilian literature: the satirical poetry of Emilio de Menezes, whose sonnets were used as sharp weapons; the presence of humor in Modernism, especially in the work of authors such as Oswald de Andrade and Barão de Itararé; and the provocative lucidity of Millôr Fernandes, an artist who critically observed with humor the social changes of the twentieth century.