We examined associations between employment and obesity, arguing that risk for unhealthy weight may vary across occupational groups because they shape workplace exposures, social class standing, material resources, and norms and expectations about healthy behaviors and weight. We used a large sample of 51-61-year-old workers from the Health and Retirement study, tracking their body mass index (BMI) over time while accounting for potentially confounding influences of socioeconomic status and gender and exploring whether gender modified associations between occupational group, BMI, and retirement timing. Compared with women in professional occupations, women managers were less likely to be obese at baseline and were less likely to be in the obese upward trajectory class, while female professionals and operators and laborers were less likely than women in farm and precision production to be in the normal stable trajectory. Male professionals were less likely than men in sales, service, and operator and laborer positions to be obese at baseline and more often followed the normal upward trajectory than most other groups, though they and farm and precision production men were more likely to be in the overweight to obese trajectory than men in service occupations. Adjustment for sociodemographic and lifestyle characteristics reduced associations more for men than for women. While retirement risk differed across occupational groups, most of these differences were explained by socioeconomic, demographic, and lifestyle characteristics, especially for men. Obesity at baseline was an independent predictor of retirement but did not further explain differences in the timing of retirement by occupational group.