I presume earlier cars had a four-speed box plus a two-speed overdrive box "in series" because it was easier to do this than to design a gearbox that had 5 or 6 ratios.
What changed, around the time of the first British cars with 5-speed gearboxes, that allowed 5-speed to become possible and later standard? I believe the Austin Maxi was one of the first to have 5-speed.