This is the oldest pipe I own:
It was either my grandfather's or my great-grandfather'. I can't smoke it right now as it needs a new stem. I've been told it dates from the turn of the last century.
This is the oldest one I actually smoke:
That's a Dr. Grabow Rivera that my other grandfather smoked all while I was growing up. I don't really like the way it smokes, but I load it up with Prince Albert every once in a while just for nostalgia. I've seen pictures of him smoking it in the late thirties or early forties. (At least I think it's that pipe).
This one actually gets smoked fairly frequently:
It's a Medico Seafoam I received as a High School graduation present in 1965.