The main objective of this paper is to develop quantitative measures for describing the diversity, homogeneity, and similarity of archaeological data. It presents new approaches to characterize the relationship between archaeological assemblages by utilizing entropy and its related attributes, primarily diversity, and by drawing inspiration from ecology. Our starting premise is that diachronic changes in our data provide a distorted reflection of social processes and that spatial differences in data indicate cultural distancing. To investigate this premise, we adopt a parsimonious approach for comparing assemblage profiles employing and comparing a range of (Hill) diversities, which enable us to exploit different aspects of the data. The modelling is tested on two seemingly large datasets: a Late Bronze Age Cretan dataset with circa 13,700 entries (compiled by PG); and a 4th millennium Western Tripolye dataset with circa 25,000 entries (compiled by AD). The contrast between the strongly geographically and culturally heterogeneous Bronze Age Crete and the strongly homogeneous Western Tripolye culture in the Southern Bug and Dnieper interfluve show the successes and limitations of our approach. Despite the seemingly large size of our datasets, these data highlight limitations that confine their utility to non-semantic analysis. This requires us to consider different ways of treating and aggregating assemblages, either as censuses or samples, contingent upon the degree of representativeness of the data. While our premise, that changes in data reflect societal changes, is supported, it is not definitively confirmed. Consequently, this paper also exemplifies the limitations of large archaeological datasets for such analyses.