The paper adopts a long-term perspective in analysing the association between health and employment histories, often characterized by substantial mobility over time across multiple statuses and contractual arrangements. The available evidence is largely based on static or short-run dynamic approaches and is restricted to the comparison between few employment statuses. We investigate how different longitudinal employment trajectories defined over multiple yearly labour market states are associated with self-reported health in middle life. We use a unique dataset linking the Italian component of the EU-SILC cross-sectional samples (2004-2012) with individuals’ complete working histories from the National Social Security registers. We apply sequence and cluster analysis to reconstruct individual working histories between age 15 to 45 and to identify typical trajectories. We then estimate the association between employment trajectories and self-reported health at age 45.Trajectories characterized by intermittent working episodes and long periods of unemployment or inactivity are associated with worse health at age 45. Long-term exposure to blue-collar jobs (potentially physically demanding, more exposed to work accidents and allowing for low levels of individual control) operates similarly to persisting/intermittent joblessness in terms of health outcomes.Unlike “point-in-time” approaches, our sequence analysis application provides unique insights on the fact that the association between the configuration of complete trajectories as they unfold over time and health in middle life are significant and substantive over and above the time spent in specific labor market arrangements (e.g. unemployment) and type of occupation (e.g. blue collars).