The article describes stand-up comedy in Estonia in relation to the local history of the genre. The aim is to cast light upon how the cultural context, but also the performer and audience interaction, works in achieving popularity of comic performance. The figure of a comedian as a “negative exemplar” as described by Lawrence Mintz in 1985, provides an excellent entrance point into discussing the different degrees of status of the genre in both the Soviet period and recent years. Two periods in Estonian history – totalitarian Soviet time and democratic present time – are under surveillance. During the Soviet period, public shows and recordings of estrada performances were highly valued among the audiences, providing commentary on the shortcomings of the regime and daily life in a seemingly innocent manner. The topics and popularity of the most iconic of these performances are analysed side by side with the repertoire of comedians from Comedy Estonia. The latter, a recent importer of Anglo-American tradition of stand-up in Estonia, also has a devoted audience and established topics, but these differ significantly from the Soviet predecessor, that of estrada. Through a historically situated analysis, it is possible to describe the adoption of traditions (and texts within it) in a meaningful way, so that foreign becomes native and starts functioning as an aspect of collective identity, be it on the level of the entire nation or just a group of fans. The empirical part of the study presents material from both periods, referring comparatively to some legendary comic texts from the Soviet period and routines of Comedy Estonia comedians. The main focus of the analysis is on the topics and targets that are prevalent in these very distinctive periods and, consequently, on the popularity of the different “stages” of local Estonian stand-up.