I bought a big bunch of these from a dealer at a SoonerCon ten years ago or more. I think the copyright date reads "1975."
The Superman/DC Legend summarized in the text is straight Silver Age glory.
The first cup, Jor-El, and Lara, shows art by King Curt Swan. I believe it's straight from the "Superman Family" piece that originally appeared on the rear of a 1960s 80-Page Giant:
I can't ID a source for the Ma and Pa Kent images offhand, but it's clear they are from the pencil of George Pap, who was a chief Superboy penciller roughly 1958-1968. His depictions of the Kents make 'em look like gentle farm folks -- too gentle, I always thought.
From Superboy #85, 1960, here's an example of Papp's take on the characters:
Someday I hope to learn and share more about these 7-11 cups.
See you next time!