Recent auction win: a “Blondie” strip from 1940 by Chic Young and Jim Raymond. The history buff in me is happy that now having something from 1940 has my original art collection of strips and pages have art from each decade spanning from the 1920’s thru this year.
My oldest piece of comics original art is a 1939 Milt Caniff TERRY AND THE PIRATES, a daily strip where Terry first catches sight of new character April Kane.
I don't have any original comics art, but I have a couple of prints from the 1930's by Mac Raboy and Béla Záboly. The Raboy print is particularly nice.