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Walther TPH in 22LR. It had about a 25 pound double action pull. It also sliced the hell out of my hand whenever I fired it single action.
 
When I was about 16 I was handed down a Remington 721 in .270 Win. The unique thing about it was that it was the first Remington made with a round receiver that could be made with a lathe instead of a milling machine. The receiver not only cost less to make, it was super light. The whole rifle weighed something like 6 pounds. In .270 Win a 6 pound rifle will take your head off. My dad eventually hollowed out the butt stock under the butt plate and added a pound or two of lead to make it a little more civilized. I'm told they made that same model in .300 H&H Mag. I would NOT fire one of those under ANY circumstances.
 
PPQ 40 gave me bilsters, was pointing at the ceiling after every round, and generally felt like it wanted to tear my hand off, but damned if it didn't put the tightest group I've done without a shoulder stock.

MP5 full-auto felt like a toy and couldn't hit a barn from the inside, even single shots. A rental gun, likely abused and worn-out.

Colt 1911 45, also a range gun, also couldn't hit a damn thing.

My 1942 Mosin feels like it was designed to be dropped repeatedly and survive, with little regard for the dropper... which is quite possibly this gun's actual history. Enemy at the Gates was, best as I can tell, a minor exaggeration. The first time I took it to the range it was before I learned the chin weld and bracing it on my pectoral, not shoulder. That was one of maybe two times I've ever bruised.

458 H&H someone had me shoot right after the Mosin felt like... if the Mosin was a 200lb biker in a barfight, the H&H was his gentlemanly-trained trained heavyweight boxer cousin. Hits at least as hard but somehow more civilized, less barbaric. They told me after two shots with the 458 that I had a s--t eating grin on my face.

Cheap Century AK (probably VSKA) stopped self-cocking after a few rounds due to some misaligned components, and shots seemed all over the place. My new ZPAP is far better.
 
Yeah, everybody thinks about the pre-64s as being the Holy Grail.
But they have poorly designed stocks for any caliber, and too light of weight for the heavy calibers.
The newer ones made in Portugal have a properly shaped stock for better recoil control.
I have one in 30-06 and have shot it with two different stocks. With the standard stock and an ancient buttpad that was as hard as a rock, it was one of the worst rifles I shot. Changing the gun over to a Monte Carlo style (also a Winchester stock), even with the steel buttplate, made a pretty big difference. The change in length of pull was a huge part of that difference in recoil, too.
.45 ACP AMT BackUp. Fired first shot, stopped and looked at it to see if it had blown-up. Finished the magazine, packed it up and sold it. My .357 model 60 is pleasant by comparison.
I didn't think the recoil was all that bad, but the terrible trigger, the lack of sights (and accuracy!) and the fact that it was obvious I was carrying a block of steel made this easy to trade off. I traded it for a Model 60 I carried for a couple of years.
I had a 649 2 1/8" several years ago that was somewhat painful, but it was acceptable considering the potential use of the gun. Very recently I acquired a 60-15 with a 3" barrel and adjustable sights. It definitely throws fire when shooting 357 ammo, but it's tolerable. I plan on packing it a bunch, but I am slightly concerned that it won't like too much Magnum ammo use.

I've shot lots of boomers, 45-70 with hot loads and a crescent steel buttplate, double barrel .410 "derringer", 5" S&W500 :)D), 375 Ruger... But the worst, most uncomfortable POS has to be that Turkey Special shotgun a buddy had. I think it was a Remington and it had some abortion of an AR15 style butt on it. Shooting 3 1/2" loads, even from standing that sucker smashed my thumb into my nose every F-in time. I'm glad I wasn't the guy that spent money buying it!
 
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Polish P-64. Probably the worst DA trigger ever and extremely snappy recoil. It's probably the only gun I got rid of solely on account of its unpleasantness.
 
Polish P-64. Probably the worst DA trigger ever and extremely snappy recoil. It's probably the only gun I got rid of solely on account of its unpleasantness.
Ever compared it to a p-83? I have debated getting a p-64 to add in as that is one of the last makarov variants I don't own.
 
I have a little Taurus 85 ultralight that I am not particularly fond of. Its just too small and I can barely hold it correctly. I have been forcing myself to shoot it more and actually manage to hit stuff at 20 yards. Still don't enjoy it.
 
Keltec P11. The one I shot was inaccurate, unreliable, and unpleasant to shoot. Probably would have done more damage if I handed it to my assailant instead.
 
AMT AutoMag V in 50 AE. Stupid recoil with no compensation. You need a giant hand to hold it. A friend of mine bought one for over $1k and thought is was the worst money ever spent on a firearm. Basically a 1911 chambered in 50 AE.
 
I have a little Taurus 85 ultralight that I am not particularly fond of. Its just too small and I can barely hold it correctly. I have been forcing myself to shoot it more and actually manage to hit stuff at 20 yards. Still don't enjoy it.

Those aren't too bad with a light 38 Special load.

 
Weatherby non-ported .460 magnum, Thumb hole stocked (with too much drop) .308 Norma Magnum in a 1917 Winchester action, Ruger #3 in 45-70 in which I shot some reloads that said "WOW" on the box. Please bear in mind that at that time I regularly shot an Ithaca Mag 10 with no recoil pad just a steel buttplate, & 2-1/4 ounce lead loads, in a t-shirt on the trap range at Paine Field Gun club so I was no stranger to recoil. Bill McGuire taught me how to shoot big recoiling rifles when I had him make a stock for me back in 1982.
 
Not so much as actually unpleasant as "what the hell": I, briefly, had a Hungarian M44. It was a short Moisin with a fixed bayonet. Huge fireball and incapable of even minute of broadside of barn accuracy.
 
Mossberg 500 bolt action 30-06. I received it as a gift. My brother laughed at me because I cringed so much. He fired it and wouldn't fire another round.
My 338 lapua had less felt recoil.
 

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