Didn't guess:
The Giver
Brian Robeson
Cheetahmen
Gabe
Hardy Boys

Did guess:
Bullet Bill
Basically every character from Ender's Game and Shadow
Got Navi in 16 questions

Haha, if you answer yes every time he guesses "some guy who always clicks 'yes'".

Fucking thing got Roman Bellic from GTAIV. Too bad it didn't ask the question "Does your character call you all the time and thus annoy the fuck out of you?"

EDIT:
Also got the whole of SG-1, Serenity crew and all of our very own Light Warriors except Thief. And Red Mage on the second try.

It can't guess Kira from Dokapon Kingdom yet. Not surprising, given that tonight is the first night I've been successful at finding a picture of her on the internet.

What the heck? It guessed Franklin Pierce at 20 questions! I thought he'd be one of the more obscure presidents.

He can't guess Dynomite from Robot Dinosaurs That Shoot Beams When They Roar. That's depressing.

Managed to get Emperor Joshua Norton.
Didn't get Father though. Odd.

If you answer 'No' to that and then keep answering Yes you get this
http://i991.photobucket.com/albums/a...g?t=1276142096
Followed by Bigfoot and then 'fatale'.

Failed to get Retsu Fukami (GekiBlue).

He got CMOT Dibbler in 25! He guessed Moist Von Lipwig after 20.

Edit: Dave from HS as well. Gonna try parson gotti next.

He guessed Grimlock in 32, after guessing Optimus Prime and Optimus Primal.

EDIT: He did not get George from Bob and George.

He got Transcendent One from Planescape: Torment, but I forgot how many questions it took him. That's pretty insane.

Took two sets of questions but he got the Pyro

That thing is awesome...

FYI I Check for Spies