The Baby Boomers have had it easiest. That's the people born between 1945 and 1955. But the people born between 1935 and 1945 had a lot of their benefits too.
The only downside is that they were kids when WW2 was going on. (Not a big deal in the US, but being a kid in Europe in '39-'45 was not fun. Being a kid in Asia in those years was probably worse). But the people born between 1930 and 1955 have had the best/cheapest education, the easiest circumstance to make a career. They got to retire at ridiculous young ages. (Some as young as 52. For years, babyboomers got to retire at age 57 in my country). Their generation built up the national debts in many countries. They lived to see a lot of improvements in the sixties and seventies. I don't think they have a lot to complain about.
People born in the 18th century or earlier had a completely different life. Without the luxury of modern life. Without decent healthcare. (Pneumonia still killed loads of people. All the diseases like polio, tbc, were around. Not fun). No cars, no planes, no tv, no Internet.
People born between 1900 and 1935 didn't have an easy time either. My grandfather was born in 1898. Live through both WW1 and WW2. (Yeah, you yanks don't care. But for some countries, WW1 was actually a lot worse than WW2. E.g. ask the Belgians). Basically your whole life between 20 years and 50 years old was fucked up by war.
The people born after 1955 are having less benefits than the babyboomers did. I've heard the generation born between 1955 and 1965 referred to as "the lost generation". They started their careers in the eighties, when the economies had slowed down. Public services like cheap/free education were taken away. By the time the lost generation is 60+ years, they have to work until 70 years old before they can retire.
I'm not saying the lost generation had it worse than the people born after 1965. In some ways they had it easier, in some ways they had it harder. I'm just saying that the generations between 1935 and 1955 had some real benefits compared to the people born after them. So yeah, if "born 50 years earlier" means you would have been born between '35 and '55, maybe it would've been better to be born earlier. If 50 years earlier means being born between 1900 and 1935, then no, you definitely don't wanna be born then.