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This study examines cross-national variation in family life course pluralization (the diversity of typical trajectory types within a population) and differentiation (the within-sequence complexity of family states over time) among individuals born 1944-1954 in five market-oriented regimes: Chile, England, Ireland, Switzerland, and the United States. Using harmonized retrospective life-history data, we reconstruct annual family states from ages 15 to 65 and apply sequence and cluster analysis to identify representative trajectory types as indicators of pluralization. Differentiation is assessed through a sequence complexity index that combines the number of transitions and the diversity of states. Results confirm pronounced heterogeneity within market-oriented countries. Pluralization ranges from four dominant trajectory types in Ireland and Switzerland to nine in the United States, with Chile and England in between. Complexity levels also vary across countries and are patterned by gender and education, particularly in Chile and the United States. Through a framework that links market-oriented institutional configurations to family trajectories, we suggest that family life course pluralization and differentiation within and between market-oriented regimes relates to (i) the timing and restrictiveness of family-law change, (ii) religious-cultural legacies, and (iii) inequality and market dependence shaping stratified opportunity structures. These findings provide a method-consistent comparative mapping of family trajectory diversity in market-oriented contexts and clarify how shared market-oriented principles coexist with country-specific historical, cultural, and policy pathways.