The Tootsie Roll owl is older than that… it dates back to 1968

the media has always held owls to impossibly high standards

"Until the second half of the twentieth century, mortarboards were often worn by schoolteachers, and the hat remains an icon of the teaching profession." [source]

So they weren't saying that he just graduated, they were saying that he was learned (the tortoise even says, "he is the wisest of us all").

That's how it used to be. You asked questions to people who were believed to be wise, and then their answer was what the truth was. And most of the things we "knew" were just wrong.

Not that it's less complicated now...

You're focused on that? Why was the boy naked with only a tootsie pop, and talking to an owl?