What's the biggest handgun you've carried IWB?

A HiPoint c9, and was not comfortable at all. It feels twice as heavy than it actually is and larger than its actual measurements.
 
Largest revolver carried, 5" N-frame M-27.
Largest revolver carried comfortably IWB (a relative term), 4" N-frame (M-25, M-58, .38/44HD, etc.)
Hoffner's Miurage--strange name, really neat Kydex holster. It rides high--the cylinder is above the belt. I first bought one for the N-frame, and liked it enough that I then bought one for the K-frame. Moved the aft loop from original position to the rear, where the pinch bolt is. Made a lot of difference. If they made one for the J-frame I'd buy one (or two). Not sure they are still in business--didn't have much luck googling them, but you can find a few pics, and you might find a used one somewhere....
Also have an SGH Side Guard Holsters leather IWB that is pretty nice--not as comfortable as the Hoffner's...fair bit bulkier.

Largest semi-auto pistol carried--full size 1911.
Largest semi-auto pistol carried comfortably IWB--Commander-sized 1911.
Lou Alessi IWB or UBG Stryker (http://www.ubgholsters.com/styled-13/#!/IWB/c/28172980) or the perennial favorite, the Milt Sparks Versa-Max (the Alessi and the UBG are thinner, the Versa-Max is easier to re-holster). A shout out to Nate at UBG Holsters (UBG=Ugly Bald Guy, he has a sense of humor, and is great to deal with) for making what is a close second place to the Alessi holster--again, slimmer than the Versa-Max. I have one for my Kahr P45 and one for a 4" 1911 (commandeered by my wife, so I probably need to buy another LOL)

Last couple of winters (in TX, again a relative term), I have tried shoulder holsters, and IMHO, something the size of an N-frame or a 1911 is better suited to a shoulder holster...but that only really works with a cover garment, so only good from Nov-Mar if I'm lucky. I can carry the same handgun in the summer time with the above-named holsters, with a bit of effort. But TBH, I am looking forward to retirement end of this year, and moving a bit North, where the weather is more agreeable.

FWIW, I'm 67 y.o., 5'9" and 150 lbs.
 
I carry a Blackhawk daily, both OWB and IWB. I conceal it better IWB, though not invisible if you're really looking, but invisible enough I have been many places where I would have been asked to remove my firearm or my person if it'd been obvious.

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Thank you.

Why do you choose a Blackhawk for your EDC?
I used to carry a semi-auto of some variety (latest was a 1911), but I would take my guns to the range and force myself to shoot a magazine or two from my carry gun (actually I didn't shoot it every time), then shoot my Single Six and Blackhawk for most of the time. I've been shooting primarily Ruger New Model single actions for the last 20 years, and they are the most natural to me of any gun, so I finally decided to just carry one all the time.
 
This is me with a 4" .500 Magnum.

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It started out as a bet/dare with a local CCW trainer, and the lessons learned from it are useful to me.

In a Tucker "Texas Heritage" holster, under a fishing shirt, it hides completely. I wouldn't call it "comfortable", but it's tolerable - I wore it for two weeks while vacationing in a national park featuring big bears and hoplophobe tourists, and emerged uncrippled - but a heavy laminated gunbelt and non-stretch leather suspenders were required to make it work. The lesson, for me, was that the belt-and-suspenders approach made more reasonable guns - like a 4" K frame - disappear almost entirely.
 
Biggest is my Colt .45ACP handgun. When I've carried it I've mostly just stuffed it inside my waistband and not even used a holster. It just feels fine that way for me.
When not stuffed in my waistband it's in a Purdy Gear holster outside.

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I've carried N-frame S&Ws and Colt SAAs concealed but not IWB. Largest gun I've carried IWB was a Colt Government Model 45 in a Milt Sparks version of the original "Summer Special". Carried a spare Magazine on the weak hand side in a single mag pouch Mile made for me as well. As I got older and started injuring my lower spine on the job (deputy sheriff) I switched to a Commander as a detective and when off duty. And that was the original alloy framed Commander, The steel version was the "Combat Commander".

Dave
 
Without being made? A Baretta 84f (380 ACP). But I'm pretty lean, so IWB mandates smaller guns for me, unless I want to dress like I'm wearing my big brother's clothes. If I did dress with very loose pants and a very large sweat shirt, I could go larger in caliber. But I'd probably get more eyeballs checking me out that way then if I dressed with fitting clothes that showed a slight IWB gun reveal bulge.
 
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