A good friend of mine has probably shot more bears than most of us will see. I remember one summer when he shot 67 or 68 bears. He was the government predator hunter in that area for many years. Most were shot with a 270 Winchester using 130 Silvertip factory loads. He had a few interesting experiences. One of the more amusing was a bear he had trapped and shot with a .22. He put the bear in the back of the truck to haul it to the disposal site and was driving on the highway. He glanced into his driver's side mirror and the bear was sitting up, head out in the wind, with his lips flapping. He looked just like a black lab out for a ride. When they arrived at the disposal site, my friend had to climb out on the passenger side and finish the bear with his 357 which settled it down well.
I worked for a time maintaining Forest Service campgrounds and would occasionally have to deal with bears. One of the best reactions I got out of a bear was when I saw one (a small bear) which had tipped over a garbage can and was in the barrel with only his rump exposed. I shot him in the butt with a Wrist Rocket slingshot and a 45 caliber lead ball. When the ball hit, he drove into the bottom of the can hard enough to slide it along the ground. When he got turned around he shot out of there like a rocket. GD