This Article provides the findings of an empirical study of 187 court cases in which the issue of the unconscionability of a contract or a contract term was addressed by the courts. The cases were drawn from two time periods. The first set of cases can be viewed as the first generation of Uniform Commercial Code (U.C.C.)-style unconscionability cases from 1968-1980. The second generation of unconscionability cases were from the time period of 1991-2003. The two groups of cases allow us to not only analyze a series of questions and factors, but also to make intergenerational or longitudinal observations. The analysis is directed at answering four questions: (1) What are the standards used by courts in making unconscionability decisions?, (2) What type of evidence is considered by courts in making their decisions?, (3) What are the operative facts or factors that are most predictive of unconscionability decisions?, and (4) How do these findings inform us on the doctrine of unconscionability both as to its reflection in the law (expressed doctrine) and in application (law in fact)?