My old 582 Rem 22LR isn't quite 50 yet but was my 1st gun of any kind in the mid 60's.
The M99R 250 Savage the family got me on my 50th birthday just happens to of been built in 1953, same year I was born. I hunt with it more than some of the more modern rifles in the safe.

The old timer in my small collection is a M94 Marlin made in 1906 chambered in 25-20 WCF. This one has a Williams 5-D receiver sight, has a liner to replace the nasty bore it once had, and shoots cast bullets like a house afire. Plenty of rabbit and squirrels have been taken with it, as well as a whitetail buck.