Our Chippy was built in 1951 and so is marginally younger than me.
Flown on an AN2, but I think that just looked old. And flown P1 in a Waco that looked very old, but was a modern replica.
The oldest I've flown as P1 is an L4 Cub, G-BHXY, in which I have a good few hours, and which IIRC was built in 1944.
SSD