I argue that since we never actually see the fall guy land, and that it is usually the landing (not the fall) that causes the pain, that the fall guy has not actually experienced anywhere near the pain being credited for.
Albeit I think they are suffering much more psychological pain, being almost perpetually falling, often with other potential threats right next to them. I imagine it must be traumatic to live through.
Such a masterpiece comedy. My favorite part of that O.J. Simpson scene is while getting shot multiple times and injured, he gets paint on his jacket and says "Oh no". So silly, but I love it.
Kenny McCormick. Little dude dies a horrible death, gets resurrected and then nobody, not even his parents, remembers that he died. And that happens several times a year.
Cage from Edge of Tomorrow. Purely from the number of day resets he goes through.
Maybe Phil from Groundhog day is a second place - same reason, just fewer deaths...