Humorous discourse often conveys meanings that differ from the literal interpretation of an utterance, making the flouting of conversational maxims a significant topic in pragmatic studies. However, previous studies have generally examined multiple conversational maxims, while focused analysis of the flouting of the maxim of quality in stand-up comedy, particularly through context-of-situation analysis, remains limited. This study investigates how the flouting of the maxim of quality is employed in American Boy: Marcello Hernandez's stand-up comedy performance and explains how humorous meanings are constructed through the context of situation. A descriptive qualitative approach was employed by using Grice's (1975) Cooperative Principle as the primary analytical framework and Halliday and Hasan's (1989) theory of context of situation as the supporting framework. The data consisted of 16 utterances identified as instances of flouting the maxim of quality, which were collected through observation and documentation techniques. The findings indicate that the comedian realizes the flouting of the maxim of quality through hyperbole, metaphor, and irony, with hyperbole accounting for 12 utterances (75%), while metaphor and irony each account for two utterances (12.5%). Rather than functioning merely as humorous expressions, these mechanisms encourage interpretation beyond the literal meaning while reflecting Marcello's childhood and family experiences. The analysis also shows that the interpretation of conversational implicatures is closely related to the interaction of field, tenor, and mode, which provides the contextual basis for understanding the intended humor. Overall, the findings suggest that humorous meaning in stand-up comedy emerges from the interaction of linguistic choices, situational context, and personal experience, while the integration of Grice's Cooperative Principle with Halliday and Hasan's context of situation provides a contextual perspective for analyzing quality-maxim flouting.