My Grandpa got hired by TWA in 1953 upon his return from Korea. He flew from 1953 until his retirement in December of 1984 - about 6 months before Icahn bought the airline. Not sure if it was the "best" time - but living in Kansas City (TWA's headquarters at the time) it seemed pretty glamorous. The transition from props to jets was a huge and exciting transition, the airlines were regulated, pay was great - just seems like he hit the timeline jackpot.