For physical pain, probably that time I slipped on a snow-covered patch of ice and did an involuntary front split, ripping the shit out of my left hamstring. A kind passer-by helped me hobble back to my front door a block away, whereupon I phoned in to work and somehow drove myself to a sports medicine clinic. Any attempt to sit down was excruciating. Only thing that saved me was that I was diligent about applying ice packs for the first 2 days, and managed to make it to work and band practice on the third day.
As for emotional pain, definitely my divorce.
As for emotional pain, definitely my divorce.