Existing research focused on social role destabilization (historical increases in role instability) and destandardization (historical increases in variability of role instability) has primarily focused on discrete social roles during discrete periods of development. Building on this work, we applied a macro approach to elucidate the extent to which historical trends toward destabilization and destandardization are occurring at the aggregate among a key set of social roles (union formation, education, residential independence, and employment) and across the whole of adulthood. Applying a historical-developmental approach, we also document how historical trends toward destabilization and destandardization vary by age. We used 3 historical, longitudinal data sets: the Monitoring the Future study (N = 69,464; 55.4% women; 75.5% white), the Panel Study of Income Dynamics (N = 45,001; 51.4% women; 54.3% white), and The Health and Retirement Study (N = 30,913; 53.6% women; 75.6% white) that collectively cover the entire adult life course and over a century of U.S. birth cohorts. We found that aggregate destabilization and destandardization have occurred across the entirety of adulthood, although trends appear more pronounced at either end of the adult life course and the specific roles driving both trends vary across the adult life course. Findings were robust for educational attainment, and destabilization and destandardization were more pronounced among women. Findings highlight the importance of considering social role changes at the aggregate and singularly, and the need to evaluate social role changes in any 1 period of adulthood in conjunction with those occurring in other periods of adulthood. (PsycInfo Database Record (c) 2022 APA, all rights reserved).