My dad's Sheridan Blue-Streak, which he bought new when he was 13 years old (1960). I learned all my shooting basics with this air rifle, and now that I'm teaching my grand-kids to shoot, he's decided it's time to pass the torch! This is awesome... they don't make them like this anymore!
... AND my grandpa's Winchester Model 42 (made in 1937). The first time my grandpa took me pheasant hunting (I was 12 years old), he brought this .410 for me to use. I got three pheasants that day, and I was hooked! I sure miss him, he passed away in '15 at the age of 91 (and we hunted ducks together until he was 90). Now that this shotgun is mine, I'll teach my grandchildren to hunt with it as well.