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A central problem of life course analysis concerns the changes brought about by the pluralization and differentiation of biographies in western societies. Lives would be increasingly dissimilar from each other and marked by a broader range of transitions and stages. Under the lens of life course theorization, the heterogenization of biographies is typically understood as destandardization. However, if the destandardization hypothesis gained momentum, there is still little information about its explanatory power outside the wealthiest centres of Europe and North America. Following recent trends in research, the article critically examines the applicability of the destandardization hypothesis to the Portuguese case. Through an analysis of the lives of three generations of Portuguese men and women, we reconstruct the life trajectories of each generation starting from the 1930s until the early 2000s. Through the …