This chapter describes the dynamics of the development and the current state of the advertising industry in the Russian Federation from 2000 to 2019. Using an historical and discursive approach that takes into account socioeconomic factors, the authors systematically consider the legislative regulation of advertising in the Russian Federation that represent the main state institutions that oversee compliance with advertising legislation. In addition to the description of control and supervision by state bodies, the chapter provides a brief description of self-regulatory institutions of the Russian advertising industry and shows the dynamics of their influence. The chapter gives a brief description of the key players in the Russian advertising market that represent Russian associations of advertising producers. Based on industry analytics as well as state and departmental statistics, the structural parameters and dynamics of the Russian advertising market in cost and financial indicators are shown. A separate section of the chapter is devoted to the latest trends in the advertising market of the Russian Federation and the most striking projects of recent years. Technologically, the trends are in line with world trends—with a significant increase in online advertising and online video, the transition to mobile platforms, the use of gamification technologies when interacting with a consumer of advertising content, and the algorithm for targeting content on social networks. The authors emphasize the growth of consumer resistance to direct advertising and note the growing interest in native advertising.