I have really enjoyed catching back up on this thread!
For me I think it would be either an old Winchester .22lr single shot rifle my dad gave me about 15 years ago. Nothing fancy or rare about it. EXCEPT...it was his first rifle that he bought with his own money when he was around 11 years old back in the mid 50's. His father wasn't a big hunter, but some of his uncles were so dad carried the .22 all over southern GA shooting squirrels, rabbits, armadillos, and whatever else they happened to be hunting. Dad had it cleaned up and gave it to me. I still shoot it from time to time, and it is amazing for teaching new shooters as it is simple to use, accurate, and the one shot is nice.
The other is a Ruger Light Weight Single-Six with the flat gate. They were only sold for around a year back in 57/58 or so. The one I have is in "customized shape"... See...apparently my grandfather (who died before I could form memories of him) was a bit of a drinker. So, apparently one day he had had a bit to drink and fancied himself a cowboy, so he tried to scribe his initials into the side of the pistol. It looks as bad as one could imagine. He also apparently tried to use it as a hammer once...because vodka. Story goes he put a hole in the floor at least once trying to master the quick draw. So...now when I look at this old thing, that still shoots like a laser beam, I am reminded of the silly antics of a man I never met, but apparently did a good enough job to have a son that trained me to properly handle and care for firearms.