Oldest would be the "Defender" pocket pistol in .32 Short Rimfire from about (?) the 1880's or so. Looks sort of like the S&W tip up picture that watch4bear posted at the start of this thread. Except it's not a tip up and was the "el-cheapo" Saturday Night Special of its day. One of my late uncles picked it up somewhere decades ago. Never fired it and wouldn't even if I had any ammo for it. All the internals are worn and it's hard to even get the hammer to stay cocked. They were meant to be carried a lot and shot a little. Other than that my oldest is an Erfurt 1916 German Luger .
