The United States and Europe are often contrasted with each other regarding their approach to freedom of expression. Yet, despite the differences between their respective judicial systems, courts from both regions inevitably face similar interpretive challenges when dealing with humor. Our paper conducts a comparative discussion of humor-related jurisprudence from the US and Europe, mostly (but not exclusively) focusing on two landmark cases – namely Hustler v. Falwell (US Supreme Court, 1988) and Vereinigung Bildender Künstler v. Austria (European Court of Human Rights, 2007). In particular, our analysis foregrounds two aspects: 1) How courts deal with the complex relations between humor, exaggeration and factual reality; 2) The role of objective harm (as opposed to subjective offence) in distinguishing between lawful and unlawful expression, and how the subjectivity of humor interpretation can undermine this criterion. On both levels, we argue that insights from literary and linguistic theories of humor – from Simpson’s work on satirical discourse to Attardo and Raskin’s General Theory of Verbal Humor – can set the basis for a more fine-grained and systematic approach to humor across different judicial systems.