When I was a teenager, I shot a buck walking along the opposite side of a ravine I was hunting. I had been taking long shots at squirrels all day long (and missing, I might add), and when that buck walked by, I thought to myself he looked as big as a hereford bull. I really didn't think about the distance until after I had put an arrow right in the sweet spot. He made a couple of leaps and stood there looking around, confused, until he fell over and rolled down toward the creek, dead as a hammer.
When I finally calmed down, I realized just how far the shot was. I paced of 30 steps down to the creek, 4 across, and 25 back up to my arrow, which had stuck into the bank behind the buck. This was way before any range finders, but I figure the shot was around 42-45 yards.
Looking back, there is no way on this earth I'd take that shot today, even though I'm a lot better now than I was then. Aside from that, I've shot a squirrel or two over 40 steps. For deer, 23 yards.