I'm a strong proponent of 1936, especially if you have the power of foreknowledge:

too young to really remember the dustbowl

childhood in segregated schools

too young to fight in WW2 (obviously)

too young to fight in Korea

can enjoy a full 18+ year long career in any pro sport you want, if that's what you like, with much less "competition"

can go into TV or film when it's a much freer industry and you can make whatever you want

can get into gaming super early on, be an arcade or pinball pioneer or get hands-on with the earlier console gens and innovate where the giants failed

can get any other job you might want, first try, and you don't even need to apply yourself, plus you get some great pay

teenager in the 1950s

23/24 at the start of the 1960s

too old to fight in Vietnam

can go to basically any gig of any well-loved act up to 1990 and see them in their early prime

food cheap for most of your life, and good in ways that don't exist anymore (such as tallow-cooked fries)

cars cheap for most of your life, and you can drive some of today's most desirable classics for pennies on the dollar when they're brand new

can fly on concorde for most of your life

regular flights are still 100x better than they are today

minimal if any faggotry

72 years old by the time the economy crashes in 2008, so almost certainly retired before it can do any damage to your savings