Most "fun" to shoot pocket pistols..

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To increase effectiveness, I overload 25acp, 32acp, 380acp, and 9x19mm to the point that recoil is painful.

None of my pockets pistols in those cartridges are fun to shoot.

But 22LR, which I don't carry because a body shot with a 22 has no effect on a 1 pound chicken, can be a fun pocket pistol to shoot.
 
While I agree with others that I'm not very comfortable with pocket carrying my CM9(mainly due to weight fully loaded than anything else), I know several who do... and my CM9 is a ton of fun to shoot at the range. It recoils considerably less than any 9mm gun that small I've shot. Only issues I've had are front sight breaking off(replaced with a metal Trijicon night sight, easy to do yourself with just a tiny screwdriver), and I bought a 7rd magazine for it that fails to feed 115gr FMJ Federal ammo(I've tried many others, just this ammo is tempermental. It has the longest OAL of all the ammo I've tested).

I don't pocket carry it, but I can carry it IWB with no undershirt really easily. I think I'll buy a P380 or CM380 to complement it and to implement pocket carry as I've been so pleased with it.
 
It depends on your definition of a pocket gun. Some people seem to have really big pockets. I would say the closest thing I've seen to a fun pocket gun is the Sig P238.
 
Having fired pocket guns in .22, .25, .32, .380, .38 Special, and 9mm (for bigger pockets), my most fun pocket gun to fire in my experience is the discontinued Taurus TCP 732 in .32 ACP.

It has light recoil and will hit 3" targets consistently at 15 yards, even with those little fixed sights which are by far better than my Beretta Bobcat's sights.

My NAA Guardian in .32 ACP only wishes it was as fun as the Taurus. It's a good thing the Guardian is smaller otherwise it would have been moved on long ago.
 
Pocket guns... Had a few before my unfortunate boating accident:

Taurus PT22 - had 2 when they first came out. Both broke. Taurus did me right. I'd like to check out one of the new poly ones as they are much better, by all accounts, then the older models. They were fun to shoot and I still have several magazines and holsters. Would by a new poly if there was ever going to be 22LR ammo available...

S&W 2214 - great little gun. Works with Model 41/46 mags too. Love the ambi mag release in the center of the grip. Very hard to find. Large grin factor shooting this one.

Beretta 21A - even better than the PT22 as it is SA/DA. Seems less picky on ammo as well. Very fun.

P64 - beefy for pocket but still small. Nasty trigger pull. Some people claim it has the nastiest recoil they've ever felt. I don't think so. Not so much fun to shoot.

AMT Backup 38 Super - yes, it is pocketable. Trigger pull makes the P64 seem like nothing - nearly impossible. Best used as brass knuckles. Or hurl it as a projectile itself. Not fun to shoot.

Taurus 738 - lightweight, easy trigger pull, manageable recoil. As much as I'd like to bash this one, zero FTF, FTE makes it a top choice for EDC. Fun to shoot too.

Taurus 856 HyLite - magnesium 6 shot 38 Special. Probably in my pocket more than anything else. 20% more firepower than a 5 shot snubbie. Did I mention light? Fun to shoot.

Taurus 94ULSS - 9 shots of 22LR in a snub revolver package, great for certain situations. Not much lighter than the non-UltraLite model so go with the steel one if cost is an issue. And a blast to shoot after getting the trigger "broken in".
 
I know this is funny but my favorite pocket pistol to shoot is my wife's Beretta 950S Minx in .22short. It's trinket sized, you can palm it like a playing card and within ten feet can be lethal with the proper shot placement. We game each other at the range to see accuracy winner at fifteen feet. Cool little pistol. Wouldn't trust my life to it---like I would my 1911 or Sig but the topic was fun to shoot.
 
For me, the clear winner in the "fun to shoot" category is my Taurus PT 22.
Same here, and mine has never failed even with HV TC rounds. I carried it on occasion, but only as BUG, and that's what I would recommend, being a .22 and all. Fun factor is quite high, though, as a "target of opportunity" grab and go piece.
 
My favorite small pistols are the Beretta Nano, Walther PPS, Kimber Solo, Kahr P380, Kahr PM9, XDsc, Beretta PX4sc. Each gun is fun to shoot. I have had no significant problems with any of them. The recoil is lightest on the XDsc and PX4sc, but recoil is easily managed on all.
 
I now have to add the Colt 1903 Pocket Hammerless .32 to my list. A friend of mine found one dirt cheap, sent it in, and they were able to fix a few things on it. We hit the range this morning....wow! Very fun, light recoiling, and accurate.
 
Sig P238. it is comfortable to shoot, has great sights for improved accuracy, and has fine little 1911 lines.
 
Second the Phoenix, although it's not really practical for carry since it's not recommended for anything but "standard" velocity loads and you have to disable or not use most of the 2035802938092830538 safeties. Also have a Jennings J-22 that works like a champ with Minimags (remember when you could buy those?) and is great for mag dumps and surprisingly accurate for what it is.
 
Seems like we are back to where we started. About every pocket gun has been mentioned. They are all winners. That's the REAL diversity.
 
+1 on the Boberg XR9-S!

I have about 900 rounds of various 9mm through it to date and I am amazed at how comfortable and accurate this little pistol is. With proper ammunition I have had no jams or failures of any kind.

3.3" bbl, 7 + 1 rounds of +P 9mm in a sub compact 17 oz. Pkg that recoils like a H&K P7 = fun!
 
The venerable Sterling Model 302 .22LR

It took quite a bit of amateur smithing to get her to run reliably, but she now digests any .22 ammunition without a cough or hiccup. She's a hoot to shoot:

DSCN1129_zpsa510561d.jpg
 
My wife's Taurus PT-25 is fun to shoot. Seems to be a solid little gun too. I just hate trying to find .25 caliber ammo. Not as cheap to shoot as .22lr.
 
I replaced the grips on my Beretta Tomcat .32, and now it's a lot of fun to shoot. It prints a little more, but still pocketable and much more accurate.
My Radom P64 in 9x18 is also a fun gun to shoot when I'm using my own reloads. Factory ammo, not so much. And, as has been mentioned before, the P64 is right on the edge of pocketability. But still a fun gun.
 
Add the Baretta Bobcat to the list, please. You said fun to shoot nothing about selfdefense.
 
Keltec p32 is the only one I would put in that category. The PF9 I shot liked to try and jump out of my hands. Too little of a good thing I guess.
 
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