I have very vague recollections of this game but am sure I would remember it if I saw it, and was hoping someone might be able to help me out to try and find it.

I remember it being an old B&W game, likely on the Macintosh Classic or Classic II (I would sneak around and play this instead of doing my typing practice in grade school!). It was some kind of puzzle/detective game, and the main character was a shortish/stocky guy with a hat. I think it was some kind of educational game, but I can't be sure. Either way, it was on the computers sold in Canada that we had in the school around 1990-92, so I am certain it must have been a default app for the machine. I remember it having a darker feel, in the sense that the screens were generally white on black and I think most of the scenes happened at night. I think it had some side scrolling elements, but was more like the Carmen Sandiego.

Sound familiar to anyone? I know this is vague, but it would be pretty funny if I could track it down almost twenty years later

Elliot.