Milan Kundera’s success in the 1980s was partly due to his essays, which critiqued Cold War-era Europe from both east and west and helped revive the concept of Central Europe. He was one of three Czech writers to win Slovenia’s Vilenica Prize in the first eight years of its existence, along with Jan Skácel and the Czech-German Libuše Moníková. Following the award granted to Pavel Vilikovský (the only Slovak laureate to date) in 1997, Czech and Slovak writers did not win the Vilenica for nearly twenty years until Jáchym Topol’s prize in 2015. This article examines these Czech and Slovak writers as both novelists and critics of the late socialist period, reflecting the historical experience of a region of small nations surrounded by global powers.