Using the U.S. National Longitudinal Survey of Youth-1979 and a life-course lens, we used sequence analysis to chart couples’ work patterns between ages 22 and 49 (n = 5232). We then used multivariate regression analysis to examine how variations in couples’ joint work arrangements may shape individual physical and mental health and sleep behaviors at age 50. We also examined associations by gender and race-ethnicity. Our sequence analysis uncovered five joint work schedule arrangements, demonstrating heterogeneity in couples’ work trajectories. In addition, volatile work arrangements (e.g., irregular hours), by one or both members of the couple, were associated with significantly poorer physical and mental health and poorer sleep behaviors compared to couples in which neither member had such an arrangement. Furthermore, females, regardless of race-ethnicity, were more likely to have poorer health and sleep quality from volatile work than their counterparts. In contrast, non-Hispanic blacks (and Hispanics to a degree) fared well health-wise with stable standard daytime work trajectories but had poorer sleep and physical health outcomes with work trajectories characterized by volatility and uncertainty.