my oldest is a Model 1897 Winchester shotgun, made in 1907. i bought it at an estate sale this year, and it has been problematic, and i have no sentimental attachment to.
my second oldest is a Model 12 Winchester, also a 12 gauge, made in 1920. this gun was a gift from my father, who received it as payment for orchestrating the trade of a boat for a shotgun collection. the blueing is all worn off, and the action is "like silk and a bank vault", to quote Dave McC. had to replace the extractor last year, it was just plain worn out. it only took 80-odd years of hard use for something to break. one of the most interesting things is the fact that i know at least four people that have owned and used this gun at some point in the past 30 years. i hunt with some of them on occasion.
an honorable mention goes to a turkish mauser with part of the stock cut off. the story i heard growing up was that grandpa (a navy man) won it in a game of cards from a turkish sailor, and snuck it home dismantled and tucked in his sea bag (hence why the stock was cut). he used it to shoot coyotes. it was a great story.
when the rifle entered my posession, i had been in to milsurps for a while. i saw the import marks on the barrel/receiver, and was a bit disheartened. regardless, i love shooting it. if i ever have kids, i'll have a great story to tell about Grandpa and a game of cards.