Sorry for the delay. I’ll post the next frames quickly tomorrow.

Those are pretty tantalizing clues.

Paul Bunyan Tycoon

hint

I want to say Incredible Machines even though I know I’m wrong.

Not part of that series. :)

Must be more obscure than I thought.
Oh well, final frame.

Sadly I did not get into PC gaming until the early-mid 90s. That’s certainly an interesting boxart though.

I have sincerely not the singlest idea.
I don’t even understand that box.

It’s definitely very abstract isn’t it?

I mean, maybe the person thinking about the landscape is supposed to be someone who is playing a text-based computer game, but thinking of a world with a river, fruit trees, a graveyard, a church and an evil treetrunk?

But then what the heck is the wood that’s being sawed into? Does that mean the world in your imagination is really a nightmare or irritating to you somehow?

I think the sawing wood indicates snoring. That’s a somewhat common colloquialism.

edit Sawing Logs - What does sawing logs mean?.

edit edit Please note that my contribution to this thread in no way actually advances anyone’s knowledge of this horrific MS Paint box art, so it is wonderfully non-helpful. I am very curious to see wtf this is.

I was thinking they were like sheeps that the girl/boy was counting and dreaming about because there were trees, so they…
Okay your explanation makes 2000% more sense, nijimeijer ;D

You’re right nijimeijer :)

I owned this back when I had room for boxes. The game was Epic’s Dare to Dream 3, designed by Cliff Bleszinski. Around the same time as Jazz Jackrabbit. This is what it actually looked like:

New box shortly.

Ha! I actually played the shareware release (the first episode) when I was a kid. It never grabbed me, and I was a kid, so shareware didn’t really transform into purchase. I either downloaded from a BBS, or I picked up on a loose floppy at the Trenton Computer Festival (every year I’d grab loads of shareware disks at that show).

And here is another very revealing box from my collection.

Not as obscure this time. A big box for it recently sold for almost 500$ on ebay

Master of Magic of course

Wrong!

I’ve got that one beside me. The purple is all smeared and different hues. :)

Surprisingly the spellbook inside is green. I thought something about that game was solid purple as well.