Self-rated health and depressive symptoms have been shown to improve upon retirement. Participants with obesity might benefit more of retirement because of the extra work-related burden they are carrying. The present study aimed to investigate whether the association between retirement and health changes may depend upon obesity in the large French GAZEL occupational cohort during 21 years of follow-up. Methods: 17,655 men and women were included in the analyses. Self-rated health was measured on a scale from 1 to 8 with 8 being very bad. Depressive symptoms were measured at four time points by the CES-D score. Mixed models examined the association of self-rated health or depressive symptoms with time (i.e. from −10 years before to +10 years after retirement), retirement, body mass index (BMI), and their interactions. Results: Regardless of retirement, BMI was associated with poorer health. Positive BMI by time interactions showed a less favorable time course of both health indicators in the presence versus the absence of obesity (0.024 versus 0.014 and − 0.19 versus −0.07 points per year for self-rated health and depressive symptoms, respectively). However, negative BMI by retirement interactions showed that the improvement of health observed upon retirement was stronger in with the presence versus the absence of obesity (−0.4 versus −0.3 and − 2.42 versus −1.70 points for self-rated health and depressive symptoms, respectively). Conclusion: Improvement upon retirement was observed in the presence of obesity and was even higher than in the presence of normal weight and overweight.