Pir Mehmed bin Abdullah Üskübi (d. 1600s) was an Ottoman scholar-jurist who worked as a jurisconsult (müftü) in various Balkan towns, primarily in Skopje. His legal opinions (fetva), collected in two volumes, became popular reference works for Ottoman jurists, professors, and medrese students during and after his lifetime. Praised by the biographers as “the best and most eminent of the provincial müftüs” the life, career, the popular and literary reception of Pir Üskübi invite a striking comparison between the legal prescriptions of the Ottoman imperial enterprise and the factual legal practice in a local context. At the same time, in the Ottoman collective imagination as well as in scholarship, Pir Üskübi is even better known for an anecdote about his dismissal from a town’s jurisconsult position after making an obscene remark about male impotence. In fact, the source that depicts this incident—the mesnevi poem “Hamse” by the Ottoman biographer and litterateur Nevizade Atai (d. 1635)—contains other stories about Pir Üskübi’s witty exchanges with his colleagues and his habit of making fun of his own blindness. Moreover, a closer look at his fetvas reveals occasional satirical remarks embedded into his responses. What implications did this marked jocular element in Üskübi’s professional activity imply for his position as a moral authority in the local community? How did his humorous character relate to his active role as a jurisconsult in shaping the social and cultural life of the province? How can historians reconcile his intellectual reputation as an erudite scholar and his popular reception as a humorous character? By approaching humor as a potentially transgressive act irritating the boundaries of proper conduct in the religio-legal profession, this paper presents, through the case study of a popular müftü, a hitherto under-discussed facet of the tensions marking the power relations between the early modern Ottoman center and province.