James C. Scott, Seeing Like a State: How Certain Schemes to Improve the Human Condition Have Failed, 1998.

XKCD, Always try to get data good enough that you don't need to do statistics on it.
Mark Twain, Life on the Mississippi, 1883.

Jane Jacobs, The Death and Life of Great American Cities, 1961.

Rosa Luxemburg, Organizational Questions of Russian Social Democracy, The Mass Strike, the Political Party and the Trade Unions, The Russian Revolution

Credits

Image of a cow being given a physical exam ("bright or dull") courtesy Dawn Marick.