When I was about 14 or 15 or so, I used to caddy for a guy who would drink a 40 ounce bottle of whiskey on the front 9 and a 26 ounce bottle on the back 9....in a tournament! (absolute truth! This guy was a RAGING alcoholic!!) (for some reason he didn't win much....go figure, eh?)
Anyway, the first time I caddied for this guy, he pulled his tee-shot on the par-3 4th hole behind a tree. We walked up to the ball, and he said, "Well caddy, what do you think I should use here?" I said nothing.....just handed him his whiskey. I was his regular caddy for the next 2 or 3 years.
He was almost never in contention for anything (he won a KP once), but I've got some of the best stories from working with this guy. The fact that he paid way more than anyone else, was a "happy drunk", and used to let me and a couple of the other caddies hang out in his RV and drink after each tournament didn't hurt either.