Dunno why, but the font type and the art style screams DoubleFine to me, so I'm gonna say The Cave.

You've got good instincts! Your turn!

Wow, I didn't really expect to get it right! ^_^ I'd very much like to, but I haven't played The Cave yet. Still waiting to have it available DRM-free for Linux (is it even available DRM-free for any OS?)

Anyway, next one! Since I've got no imagination, I tend to pick the game I'm playing at the moment. This is no exception. :)

Nothing? Maybe the dated graphics are misleading you... it's in fact a pretty new game.

Here, have a new cropped screenshot!

It's not it, but the style reminds me of an awesome game that I'm patiently for, ie to come to gog : Impossible Creatures

No idea. But looks cute.

Nope, it's nothing like Impossible Creatures. :)

It is quite cute (when looked from afar, at least), but you don't get to contemplate it very much as it tends to get pretty frantic quite soon. Because it certainly isn't the kind of game people assume when look at it for the first time.

As an additional hint I'll say this game has been recently featured in one of the biggest Youtube gaming channels.

Oh! And it's not available on GOG. :(

Train Valley ?

We've got a winner!!! It was Train Valley indeed, a game that at first look may look like Railroad/Transport Tycoon and the likes, but in fact it's nothing like them. Instead of a building/business simulator it's basically a micro-management game with a train theme. Just take a look at TB's video to see if you may like it or not.

Your turn, _Slaugh_.

Here's a tough one...  It's not a DOS game.

It has some Indy feeling attached to it but I doubt that this is the same fedora wearing guy...

REDVWIN

The hero wears a fedora, but unlike Indy, he doesn't know how to use a whip...

Nice find, voted for it! The more trains on GOG, the better :-)

I didn't realize there was a wishlist entry for it. Voted!

Another clue:  The game was released in the early eighties.