My oldest gun is a Montgomery Ward Ranger, a .22 s/l/lr bolt action tubular repeater. It was made as early as 1943 or as late as 1946. I'm not sure because I don't know if they were making recreational firearms during WWII, but it was made no later than 1946. My dad's parents bought it for him for an ROTC class he had in high school, and they actually had an indoor rifle range at his high school. Wow, things sure have changed.
I was born in 1956, so the rifle is 10 to 13 years older than I am.
I have a early 1911 GI built around 1916. Low paper-thin sights, with the flat mainspring housing and lanyard ring. I was born about 44 years after this Colt went into service. I've been shooting this piece since I was 9-10 years old. I still shoot her today as i expect my sons will long after I'm gone...
Me, 1977. Gun, Winchester model 1892 early production 25-20. Was told it was produced sometime around 1895. Was my fathers and I inherited it when he passed away. It's in rough shape though and really needs a professional to restore it.
I have an 1880s vintage Belgian-made 12ga shotgun that came to me from my grandfather. Don't know whose it was before it was his. May have been his step-dad's.
I have a Remington 12 pump .22 from 1921. It still shoots like a dream. My 10 year old thinks it one of he coolest firearms we have (even over he 15/22 and 10/22).
I have a S&W .38 that went up SanJuan Hill with Teddy Roosevelt. (Family heirloom.) It's in great working order and I would not hesitate to fire it, but never will. I also have a black powder rifle that has yet to be dated. I've been waiting for several years to scrounge the cash to have it restored, but as soon as I get close to having money to do it I buy new functional firearms. One of these days I will do it.
I also have a Walther PP self-dated back to 1952. It's from the first civilian run that Walther produced for after WWII for commercial "sporting" sales. Not super old, but being the huge fan of Walther's that I am, it's priceless to me.
I have a WWI Era Colt revolver that my Step-Grandpa pulled off a Japanese soldier in WWII. He got full documents for it and everything. He then passed it to my dad, and my dad passed it to me this Christmas. I was born in '80.