Research in different fields shows health to be unevenly distributed across social groups and to be affected by an individual’s labor market status. The available evidence is largely based on static or short-run dynamic approaches and is restricted to few employment statuses. However, an emerging consensus points toward the need of a more long-term perspective in addressing the association between health and employment histories, often characterized by substantial mobility over time across multiple statuses and contractual arrangements. By applying sequence analyses on 11 possible yearly employment statuses, we contribute to the literature by investigating how longitudinal employment trajectories from age 15 to 45 is associated with self-reported health in middle life. We use a unique dataset that merges the Italian component of the EU-SILC cross-sectional samples with individuals’ complete working histories from the Italian National Social Security administrative archives. Our findings reveal that trajectories characterized by intermittent working episodes and long periods of unemployment or inactivity are associated with worse health at age 45; additionally, among those with a stronger attachment to the labor market, blue-collar workers report worse health than professionals, white-collar workers and public employees.