Despite improvements in life expectancy in many countries, there is uncertainty whether increase in years of healthy life expectancy has kept pace. This paper explores whether there is empirical support for the compression, dynamic equilibrium or expansion of morbidity hypotheses among successive generations of the working age population of England. Synthetic cohorts born between 1945 and 1980 (aged 25 to 64) are constructed from repeated annual cross-sections of the Health Survey for England, 1991-2014, (n = 135,189). A range of subjective and objective health outcomes are compared at the same ages across successive cohorts, and healthy life expectancy is calculated using the Sullivan method. We find that younger post-war cohorts at a given age have poorer or the same health according to self-assessed general health, long-term illness, diabetes, coronary heart disease and BMI, and better health according to high blood pressure and limiting long-term illness. We also find that healthy life expectancy has increased at a slower pace compared to total life expectancy in the 20 years between 1993 and 2013. Taken together our findings imply that for younger generations, the number of years expected to be spent with one of these health conditions has increased. Socio-economic inequalities in these same health measures are also examined, and are found to be widening across generations, especially in women. Our findings lend support to the expansion of morbidity hypothesis for most health outcomes, most notably those that are treatable, and point to an increased future demand for certain healthcare services at younger ages, especially among those from lower socio-economic groups. This will have notable implications for public healthcare providers as costs increase.