The drills on the top row look like Machine Bits, originally associated with a blacksmith's post drill, where every drill had a 1/2" diameter shank. Makes for a much faster change out on modern machines, don't crank the tool chuck open, loosen and tighten a set screw and go.
We used to make split collars like that to mount drills, etc. in holders for turret lathes and screw machines. A couple of those drills are flat bottomed, so probably from something like that.