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Popular press often portrays the millennial generation as evidencing increasing selfishness, or conversely as representing one of the most generous generations alive today. This paper investigates these contradictory claims by extending and challenging theories of individualism, collectivism, and voluntarism in explicating trends among a national, diverse, and longitudinal millennial cohort transitioning to adulthood. This analysis contributes two primary advancements to understanding youth and American culture. First, it examines the utility of traditional theories in explaining contemporary trends. Rising globalization raises questions as to the remaining relevance of classic theories in explaining contemporary trends. Second, this paper integrates a life course framework in cultural analysis. Combining these approaches, this paper investigates whether individual and collective orientations can be held in combination, and whether youth change their weighing of self and other orientations over time. Longitudinal findings indicate that the millennial cohort – who had high levels of individualism during adolescence – evidence greater collectivist and hybrid orientations as emerging adults, and promoting attention to cultural values undermines individualistic orientations.