The study is derived from a larger study, namely the author’s PhD dissertation, and it gives an overview of and illustrates the most essential factors that maneuver utterances into being perceived as humorous and/or offensive in the context of performed, edgy stand-up comedy. The paper introduces basic humor and offensive humor theories as well as certain pragmatic mechanisms that lie beneath the process which starts with the utterance and ends with the perlocutionary effect on the audience. The study elaborates on offensive humor theories, conventions of stand-up comedy, pragmatic concepts, the contrast between offensiveness and immorality, which is all complemented by a brief psychological perspective, linking people’s reactions to the notion of harm and one’s level of self-esteem. The pragmatic insight into the factors that make offensive humor function points at the necessity of strong, non-conventional, and complex stimuli, perceived and comprehended by the audience, based on which the offensive layer can be constructed.