The aim of this paper is to explore the violation of Grice's Maxims in the Arabic comedy "Madraset Al- Mushaghbeen" and explain how the violation of the maxims brings about humorous effects in the play. The analysis shows that 61 instances of maxims violation were identified in the play. Maxim of Manner receives the highest percentage of violation i.e., 24 (39.3%) compared to the other maxims. Maxims of Relevance and Quality come next, i.e., 14 (22.9%) and 13 (21.4%). Maxim of Quantity constitutes 10 number of violations (i.e., 21.4%). The study shows that most of maxim violations that create humorous situations are perceived through the following: rhetorical strategy of overstatement and personification, use of misleading conventional-coded expressions, incongruity of conversation-established concepts/ideas, and breaking of communication norms. The study also reveals that cultural and background knowledge significantly contribute to eliciting the humorous implicatures from the characters' utterances. The study concluded with the following implications: humorous implicature depends on the conventions of the speakers' community and the language shared among them; and it arises as a result of speakers' acts and/or expressions that tend to be incongruous with the behavior and concepts established in the culture of the concerned interlocutors.