My father gave me his post war colt woodsman in 1992. Actually I have an M1 Garand that I got in 1989 from DCM. I'll keep that until I die. I don't shoot it frequenly, but I get some interesting looks when I show up at a 1000yrd match with it.
I got a freaken Raven teflon plated .25. Still lying around cause what good is it as a trader? Nothing. Zinc pistol that works fine but I never shoot it. Payed like 60$ on a whim, NIB in the early 80's. First handgun. Shared some unprintable(not illegal?) adventures and does not take up much space. What the heck.
Smith & Wesson Model 19, loaned to me by my dad a number of years ago, with the clear intention that the loan was permanent (he wasn't shooting anymore).....
My first handgun purchase was a PA-63 @ a gun show around '00 at a cost of $99 + tax. I still have it in my safe, but it doesn't get many visits to the range. It's a tad on the uncomfortable side (did I just say that? ... it's down right painful once you get around 100 rds).
I bought a Colt Mk IV Series '70 Government Model .45acp in 1972,
and around 10,000 rounds later it's still sitting in my gunsafe.
I have newer, prettier, fancier guns, but that Colt will always be
my default "serious" go-to gun.
Ruger .22LR Standard that my Dad bought mailorder in the early 1960s.
The oldest I still own that I bought myself would be the 9x18 Mak (Russian) that I bought for him when he gave me the .22 and his rifles back in the early 1990s. It should have been my custom Redhawk which I bought in the mid-1980s but I sold in a fit of stupidity.