My paper is based on the author's observations of contemporary cultural landscapes in the cities of Krakow (Poland) and Lviv (Ukraine), which prompted the analysis of the observed differences through the prism of Jewish minority dynamics. Having gone through the centuries of parallel histories, which resulted in the creation of convergent landscapes, Krakow and Lviv experienced dramatic changes in the twentieth century, associated with the Nazi occupation, the Holocaust, and communist totalitarian regimes, which reduced the cities' Jewish population from a pre-war twenty-five to thirty-two percent of the total to nearly nonexistent. After the return of democracy to Eastern Europe in the early 1990s, Krakow and Lviv acquired distinctively dissimilar cultural identities, characterized by the revival of Jewish culture in Krakow and its obliteration in Lviv. The suggested explanation of the observed differences is drawn from the unevenness of nation-building processes in Eastern Europe, which resulted in the advancement of Polish cultural plurality and Ukrainian nationalism. While Polish pluralism allows for the minorities to reestablish their cultural identities, Ukrainian nationalistic movement, aimed primarily at national unity, temporarily stifles the minority discourse. The dynamics of Jewish minority identities, expressed through the evolution of cultural landscapes in Krakow and Lviv, demonstrate the array of democratization pathways in contemporary Eastern Europe.