I remember playing this on PC as a kid.
Anyone know the history behind it?
I'm not positive but it looks reminiscent of the assets in Mario Teaches Typing (or maybe MTT2). I vaguely remember playing a Mario game on PC with similar graphics, and it might've been the same shareware knock-off game.
As for Cooljerk/TSR, he did lots of posts like this on P-A forums. He was probably most famous for his "retro Sonic minutiae" thread. Stuff like old beta and game engine specifics from primarily Genesis-era Sonics. They were a really interesting read. But as he said himself, it's all old news by now that a lot of people on, say, Sonic Retro would know.