AbstractIn 2010, the Macedonian government commissioned a controversial urban project titled Skopje 2014, designed to aesthetically revamp the look of the capital’s center. The announcement gave rise to conflicting views, both supportive and critical of the idea. Part of the criticism leveled at the project was expressed through on-line humor which produced no major sociopolitical effect, public debate or counter-humor production. Yet its production and reception may be taken as emblematic of the societal tensions underlying the contradiction between its effects and its evaluations.By outlining the political context of the humor’s emergence, analyzing the examples produced, and voicing humor creators’ and citizens’ understanding of its political role, the study reflects upon humor’s specifics and limitations in order to argue that the humor produced and its understanding reflect the political impulses, tensions, and ambiguities of a hybrid society such as Macedonia. Using input from the discussions on the role of humor across political systems, and especially relying on studies of political on-line humor in democracies and audience research, the study intends to determine the political effect of the humor produced so as to argue that faced with many challenges, the humor failed to become a democratic means of political engagement, remaining largely a tool for the expression of personal dissatisfaction. Nonetheless, there is an existing paradox in the face of citizens’ beliefs in the potential of this humor. This study tries to explain this paradox.