Order sorted chronologically, though, there’s a decent argument to be made fitting each member’s personality.
And yes, I will count ENT as the tail-end of the “golden era,” seeing as VOY’s finale was 5/23/01, with ENT’s debut on 9/26/01. Pretty short refractory period, if you ask me.
TNG starts off all kinds of goofy, which is a shade of how TOS was.
True, early TNG would be a better fit. And I get that having any other series in the leftmost spot feels wrong.
Still, I’d have to go with: