The developments of Russia and Germany in the 20th century show astonishing parallels, despite the very different social, economic, and political structures of the two countries. In both countries democratic systems were established for the first time in their respective histories during and after the First World War, respectively. These failed due to their internal weaknesses and were replaced by totalitarian regimes, albeit with completely different characteristics. In both countries, the democrats were given a second chance after the collapse or erosion of the respective totalitarian regimes. However, the “second” Russian democracy that emerged in August 1991 in no way resembled the “second” German democracy—the Federal Republic founded in 1949—but had astonishing structural similarities with the failed “first” one, the Weimar Republic of 1918–1933. Analyzing all these parallels and putting them in a comparative perspective is the subject of this volume. In addition, the book takes a closer look at the authoritarian and neo-imperial turn in Russia at the end of the 20th century and its historical roots.