This study examines the non-observance of Grice's Cooperative Principle and the use of impoliteness strategies in celebrity interviews, with particular reference to "the Tonight Show Starring Jimmy Fallon. It aims to identify the types of conversational maxim violations, explore their pragmatic functions, and determine the most frequently employed impoliteness strategies. Adopting a descriptive-analytical approach, the data were collected from selected televised interviews and analyzed according to Grice's (1975) theory and Culpeper's (1996) model of impoliteness. The findings reveal that all four conversational maxims -Quantity, Quality, Relation, and Manner- are violated to varying degrees, with Quantity and Relation occurring most frequently, while bald on-record and mock impoliteness emerge as the dominant strategies, primarily serving entertainment rather than offensive purposes. These maxim violations perform several pragmatic functions, including humor creation, face-saving, topic management, audience engagement, and irony, demonstrating that non-observance is a deliberate and context-dependent communicative practice rather than a sign of communicative failure. Overall, the study highlights how cooperation and impoliteness coexist in media discourse to balance politeness and humor, contributing to pragmatic and media discourse analysis and offering directions for future research across different linguistic and cultural contexts.