Shot 460 Weatherby once, figured I could shoot it about 4 or 5 times standing before it began to be painful, ten pound rifle with scope.

Shot 45 Colt derringer once, felt like a firecracker going off in your hand.

Most painful was a CVA Kentucky rifle a buddy had built about 40 years ago.
He read you couldn't over load them, the excess power would just go out the bArrel, so he wanted to shoot it with 240 grains of powder. Like a dumbazz I told him if he shot it and it didn't blow up, I'd shoot it.
That curved brass butt plate really hurt, turned my shoulder black and blue.
We only did that once.