The chapter explores the difficult search for legitimacy in using unlicensed media content by the Russian social network, VKontakte, and other Russian Internet companies. Russia’s economy and society went through several stages, from complete negligence of intellectual rights to step-by-step shaping of new compromise principles to make consumers to pay at least something and to persuade right holder to accept at least something for music. For a better understanding of the cultural background of this story, we look back to the evolution of Russian intellectual property rights and observe similar “legitimacy of the illegal” phenomenon during several stages of its development. Two important generalizations are: (1) when deciding to act illegally, the actor wants to maximize the happiness of its most important stakeholders, and (2) the decision to change the business model and search for new legitimacy almost never comes from moral arguments, but is always made under external pressure.