Oldest that I own that I shoot, a Mauser born in 1923. Oldest that I own, I've got an 1837 French Naval boarding pistol.
I've got 2 that I want to shoot even if it is just once. I've got an 1850s British Transitional pepperbox and this one isn't as old but a Forehand & Wadsworth Swamp Angel in .41 rimfire that is from somewhere between 1871 and 1890. We've got some other old rifles that came from my great grandma's place. I believe a few were hers and a few were great grandpas. At least 1 of his was handed down to him and he was born in 1894 so a little older than that.
I have a Smith and Wesson 17-2 that I think was made in 1965 or 66. It was my grandpas, then my dad's, now it's mine, and it will be my son's revolver.
Got a single shot .22 bolt action rifle model O2A. Patent date on the barrel is 1898. 1928 is carved on the stock. My dad bought it off a guy for $5 in the 1930's. Still shoots very accurately, by the way. Stock has a major crack in it and the initial "N" is carved in it. It's the rifle I learned to shoot with.
My next oldest is a J C Higgins .270 made by FN with a Mauser action-also was my dad's. It's from around 1960.
And the third oldest was my Dad's shotgun. It's a Remington 878 Automaster. (Yes, I said 878) three shot, gas operated auto that preceded the 1100. It's from around 1962. Both still accurate and fun to shoot and in pristine shape.
I have a 1906 winchester pump-action .22 made in 1912. 20" octogon bbl. It shoots, but has a hard time extracting the shells, unless it .22shorts. I plan on sending out to be refurbished.