The Baltic people of Estonia, Lithuania, and Latvia gained recognition with their successful use of a cultural tool, singing folkloric songs, to protest collectively against their common Soviet oppressor in the summer of 1988, preceding the collapse of the Soviet Union. Rational-choice theorists have argued that large rebellious movements are paradoxical because the larger the number of potential revolutionaries, the greater the leadership, participation, and coordination problems they face (Olson, 1971; Tullock, 1974). This paper investigates Estonia’s Singing Revolution and illustrates how ethnic Estonians used their shared cultural beliefs and singing traditions as a tacit, informal institutional solution to overcome the collective-action problems with organizing and participating in mass singing protests against the Soviet regime. The paper goes further to extend the standard rational-choice framework and to include a more dynamic, entrepreneurial-institutional perspective on socio-cultural change by accounting for the role of cultural leaders as cultural entrepreneurs, a subset of institutional entrepreneurs. The success of Estonia’s Singing Revolution can be ultimately attributed to leadership in the form of cultural entrepreneurship going back to pre-Soviet Estonian times. The revived legacy of ancient shared beliefs, folkloric practices, and singing tradition represented the necessary social capital for the Estonian people to voice collectively shared preferences for political and economic governance during a window of constitutional opportunity. Mikhail Gorbachev’s Glasnost, a policy aimed to improve Soviet formal institutions by fostering freedom of speech and political transparency, also provided a context propitious for the Singing Revolution because it lowered the perceived costs of participation in the rebellious singing and opened a window of opportunity for political change.