Background: The baby-boom generation is entering retirement. Having experienced unprecedented prosperity and improved medical technology, they should be the healthiest generation ever. Methods: We compared prevalence of disease and risk factors at ages 50–61 years in baby boomers with the preceding generation and attributed differences to period or cohort effects. Data were from the Health Survey for England (HSE) from 1994 to 2007 (n = 48,563). Logistic regression models compared health status between birth cohorts. Age-period-cohort models identified cohort and period effects separately. Results: Compared to the wartime generation, the baby-boomer group was heavier (3.02 kg; 95% confidence interval [CI], 2.42–3.63; p < 0.001) and reported more diagnoses of hypertension (odds ratio [OR] = 1.48; CI, 1.27–1.72; p < 0.001), diabetes (OR = 1.71; CI, 1.37–2.12; p < 0.001), and mental illness (OR = 1.90; CI, 1.54–2.53; p < 0.001). Baby boomers reported fewer heart attacks (OR = 0.61; CI, 0.47–0.79; p < 0.001) and had lower measured blood pressures (systolic −9.51 mmHg; CI, −8.7 to −10.31; p <0.001; diastolic, −2.5 mmHg; CI, −1.99 to −3.01; p < 0.001). Higher diagnosed mental disorder prevalence was attributable to a cohort effect (prevalence for 1935–1939 cohort, 2.5%, vs.1950–1954 cohort, 4.7%), whereas changes in diagnoses of diabetes and hypertension and measured body mass index were primarily period effects. Conclusion: English baby boomers are moving toward retirement with improved cardiovascular health. However, the baby-boomer cohort has a higher prevalence of mental illness diagnoses and shows no improvement in self-rated health compared to the wartime birth cohort. There remains substantial scope to reduce health risks and future disability.