This study is an attempt to investigate medieval humor in the Ayyubid period (1171–1250). In a period of constant wars, terrible plagues, and turmoil, Ibn Mammātī wrote a pamphlet entitled Kitāb al-Fāshūsh fi Aḥkām Qarâqûsh (stupidity, or the decisions of Qarâqûsh). It is a small volume which contains words and actions that Qarâqûsh could have said or done. The book is written as an attempt to ridicule one of the most important political leaders of the Ayyubid state Emir Qarâqûsh Ibn ‘Abd Allāh al-Asadī (surnamed as Bah’āaddīn Qarâqûsh) (n.d. – April 1201). The book is so influential that historical facts are overshadowed, and overwhelmed by the humorous anecdotes that branded Qarâqûsh forever as a symbol of a lunatic tyrant. This manuscript, however, is believed to be one of the oldest books on political humor in the Egyptian history (Al-Najjār 1978: 56). Therefore, using a critical discourse analysis perspective, the study seeks to examine and analyze humor and jokes in selected anecdotes from Ibn Mammātī’s book. I have drawn upon the three-dimensional model of discourse analysis developed by Norman Fairclough (1992a, 1995a, 1995b, 2001, 2003). The study aims to prove that this pamphlet has been used in the entire Islamic world in different epochs as a defense mechanism against all the ruthless sultans, kings, rulers, and presidents. I claim that these jokes have served as a sort of recreation for the people, as a means of peaceful protest, and as a silent cry against oppression and tyranny.