I wouldn't have believed it if I wasn't there but I watched my buddy kill a rock chuck at 304 yards with his 17 HMR. He hit him right between the eyes and turned his head into a canoe (I got to watch his head explode through the scope of my 22-250). I've watched that same buddy routinely kill rock chucks between 125 and 250 yards with his 17 but 304 was by far the longest and still amazes me.
A few years ago I killed a coyote with a .17HMR at almost 250 yards with a lucky shot to the eye. Last year I shot a coyote with a .22LR at about 175. She took a couple of shots but luckily for me the first one spined her and she was unable to run away. The next two to the head finished it.
About 35 years ago, before I knew better about shooting safely, I hit a duck in a waterhole from 100 yards away with my dad's Smith & Wesson K-22 revolver. Blew his head of, hitting him just below the eye. Fluke? You bet!!!