@noiob N64 or so was the first sign of major trouble.
@noiob i think the 3d/analog stick took over as the star of the show and the d-pad suffered ever since, to varying degrees
you wouldn't think it's hard to get right, yknow? but like 90% of controllers over the last 3 decades fuck it up
a few good ones include sega genesis six-button (better than saturn imo!) and it's not great for comfort but i find ps1 digital very useable