I like what Kuzo Yoshiro has to say here. At our current point in gaming's history, I think it's more important than ever to build your own taste in video games and chase after experiences that appeal to that taste, regardless of release year. For me, that approach has had me zigzag back and forth through time.
Playing older titles makes you appreciate what ideas they figured out ahead of the curve, and playing later titles makes you appreciate which lessons were carried forward along the way!