The specific artwork seems familiar, maybe off a yearbook cover or something. I know there are paintings of the same scene.
My initial thought is remembering the bottom makers that some kids used to have.
That's "kids" with an "S" from the 70's when a button maker was considered cool or fun, not "kidz" with a "Z" after the video games came along and turned sitting on a couch staring at a tv into cool or fun.
Doug "grumpy old man" Goodman
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