I realize that what I'm about to say isn't in reply to your exact question. One: as far as I know, anything under a .40 caliber is illegal for taking deer in every state in the Union, and in some the minimum is .45 (I know of none with a .50 caliber minimum). Two: I know of no one, personally, who's taken a deer or any other relatively large animal with either of the calibers you specify. It was done, I would assume fairly frequently, in earlier days. Three: taking your question at face value (since I'm also curious about a number of things I have no intentions of actually trying), taking a deer with a .32 or .36 wouldn't be all that big a deal -- but, then, under the proper circumstances (and, no, I've never done this, either), neither is taking one with a .22 LR. Close range and shot placement are critical. In the muzzleloading equivalents of the .22, as heavy a powder charge as would burn completely in your barrel and give decent accuracy would be desirable. I don't play with maximum charges in my squirrel guns (a .32 and a .36), but I'd guesstimate, oh, maybe 40 to 50 grains of 3F. But, like I say, I don't know about top-end in these little guys. The only reason I'm venturing to guess is that I'm sure no one would be so disrespectful of the law and the animal to try taking a mature deer with a caliber known to be utterly underpowered for the task. :grin: