Stand-up comedy is said to reflect a society’s problems and fears. The influential and indeed very funny American comedians Lenny Bruce and Andy Kaufman both refused to be considered comedians. To this day, a large number of critics have thus focused on Bruce and Kaufman as social critics. Taking as a premise that stand-up comedians teach through enjoyment, this study seeks to evaluate Bruce and Kaufman’s performances with regard to their comical means used to convey socio-critical messages. Detailed analyses of both comedians’ strategies of humor enable a precise understanding of their critical messages in the first place. An evaluation of both comedians’ reception and a contextualization of their material clarifies their position as critical comedians within postmodern society. The biographical pictures 'Lenny' and 'Man on the Moon' are understood as the most influential parts of their reception and are analyzed in detail. The preservation of Lenny Bruce and Andy Kaufman’s strategies of humor and their underlying critical messages can thus be illustrated and the relevance of their comedy for today’s viewers is pointed out. Finally, the legacy of Bruce and Kaufman as pioneers of (American) stand-up comedy is emphasized.