Nifty!

Instant recognition, as I've considered drawing his love interest in the past.

I'll hold off on guessing as I'm busy.

Is that from a point & click?

It's from a look and see, yes.

The Tiny Bang Story?

My guess is Machinarium.

Oh I recognize him too. Really nice drawing.
A lot of snarky comments come to mind. Sometimes I wondered why his companion kept him around.

Naturally I'll let someone else answer this. I promised myself I wouldn't take "side projects" like these until I get done with Total Annihilation: Kingdoms, or else I would never get the damn backlog down.

No correct guesses yet ^^

It's the sidekick, Crispin, from Primordia.
http://www.gog.com/game/primordia

KrisViking already tried it and his answer was rejected. Think again.

Edit: Ninja'd

Strangely, I missed it.

No! It's the Weebo from Flubber!

You're right!

But here's another drawing for extra points: http://imgur.com/AiQbGye

Soooo... was grimwerk wrong?

The judge's servant. I'll take her as confirmation.

Here y'are: