Life course theories highlight the importance of understanding psychological health of aging individuals in context. Work and marriage are influential contexts in later life that are increasingly relevant because both spouses of many households work and individuals are delaying retirement. Although there is extensive literature on predictors of depressive symptoms, incorporating life course histories of work and social contexts has been a critical omission in the aging and health field. This study identifies couples‚Äô work trajectories as a function of husband‚Äôs and wife‚Äôs weekly work hours and examines the link between couple work-hour trajectory membership and individual depressive symptoms. Data are from 1,641 married couples who participated in the 1998‚Äì2012 waves (ages 51‚Äì89) of the Health and Retirement Study (HRS). Findings revealed 6 distinct subgroups of work-hour trajectories among couples and that membership in these subgroups was associated with depressive symptoms. Retiring husbands with wives who continued to work and wives who worked minimally throughout the years (regardless of whether their husbands worked or retired) reported more depressive symptoms than other subgroups. These results suggest that work trajectories themselves, beyond current health status, may carry differential psychological health risk. Moreover, several sociodemographic and life course factors in 1998 were significant predictors of trajectory membership. These findings provide insight into midlife factors that may influence work trajectories (and the potential health risk) through to older adulthood. They suggest that a life course examination of work and social contexts is needed for a greater understanding of individual and couple health development.