The article is devoted to anecdotes about informal economy. They tell us about corruption, theft in production, shadow entrepreneurship, informal channels of distribution of scarce goods etc. These anecdotes are a peculiar encyclopedia of soviet and post-soviet man’s patterns and stereotypes of thinking. The article develops the thesis that laughing refers to negative emotions and turns them into humor and jokes. The laughing serves as a social critic’s instrument, which emphasizes the difference between reality and expectation. The anecdotes do not solve any problems but decrease their severity and help to adopt to them. The article analyzes three periods: the USSR, Russia of 90-th and Russia after 2000. The USSR’s informal economy was based on deficit. It created informal exchanges in social networks (‘blat’) and theft in production (‘tashilovka’). In those anecdotes, the legitimation of those practices appeals to the unfairness and stupidity of soviet rules. The soviet anecdotes hyperbolized the system’s disadvantages that justified soviet people’s shadow practices as an adoptive strategy and reviving of social justice. In 90-th ‘new Russians’ became the main characters of the anecdotes. Common people jeered at entrepreneurs’ lack of education, boast, and desire to demonstrate luxury. People, who had become poor, revenged the ones whose enrichment was considered unfair. After 2000-year officials became the main characters of the anecdotes. According to those anecdotes, their greed spoils every president’s intention. In fact, those anecdotes were the way of expression people’s discontent about the results of reforms.