What's the hardest kicking handgun you have shot?

One of the most unpleasant pistols I have shot is the Polish P64 in 9mm Makarov.

Despite the not-terribly-powerful round and all-steel construction, the blowback operation, grip design, and terrible trigger make for a very un-fun and painful gun to shoot.

Similar small blowback 9mm Makarov pistols (Makarov PM and CZ-82) are far more pleasant to shoot than the P64.
 
Friend of mine's pig gun -- .454 Casull --

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My Contender

I can't see shooting anything more from my old contender than it's .44 mag barrel, the one it came with.
I've loaded .44 mild to wild, I stay away from wild with this one. It's an early Contender and the grips really punish my arthritic hands. It's pretty light too.

I'll get some rubber grips for it one of these days. Set the pretty but punishing grips away.

I have yet to succumb to the barrel fetish that goes along with owning a Contender. I like 30.30 but won't buy a barrel till I change out those grips.
 
I haven't shot a lot of pistols because I don't like pistols but it's hard to carry a shotgun in my shorts. LOL
But I think of the few I have shot my buddys .44 mag is the heaviest recoil pistol I have shot.
 
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