This article uses sequence analysis to examine how gender inequality in work-family trajectories unfolds from early adulthood until middle age in two different welfare state contexts. Results based on the National Longitudinal Survey of Youth and the German National Education Panel Study demonstrate that in Germany, all work-family trajectories are highly gender-specific irrespective of social class. In contrast, patterns of work-family interplay across the life course in the United States are, overall, less gendered, but they differ widely by social class. In fact, work-family patterns characterized by high occupational prestige are fairly equally accessible for men and women. However, women are far more likely than men to experience the joint occurrence of single parenthood and unstable low-prestige work careers in the United States. The authors contribute to the literature by bringing in a longitudinal, process-oriented life course perspective and conceptualizing work-family trajectories as interlocked, multidimensional processes.