Things he guessed right:

WALL-E
Kamina
Mario
Chrono
Raz(!)
Shantotto(!!!)
Rice Boy(! times infinity)
Bro
Poring

He totally failed at:

Iron Man(Seriously. Hmm.)
Dave Strider(I got Justin Bieber, like, twice)
Warbot
Squiddles

That last one was fucking unfair to him/it, but considering he knew Rice Boy, I didn't hold back.

he got the Sniper from tf2 in 12 Questions!
He got it with me in 11 questions

Good.. it's hard to beat it.....

Right:
Spider jerusalem
Adrian Monk
John Locke
Paine (ffx-2)
Kei (dirty pair)
Yuri (dirty pair)

Wrong:
Rick grimes (walking dead)
Doktor sleepless
John Horus (black summer)

I'm a little stumped on the distinction between "Is your character real" and "Does your character really exist". I'm guessing the first refers to actual people (George Washington, King Henry VIII), whereas the second refers to characters in actual, published media (Batman, Gordon Freeman, anyone else that isn't just "Your/Someone Else's Original Character", for which he apparantly has an entry). Could someone clarify?

He got:

Dr. Tran
Elle Driver (tried to guess The Bride first, though - understandable)
Premier Alexander Romanov (!!!)
Chell (thirteen questions!)

He Failed:

Durkon Thundershield
Jill Fizzart (Fire Emblem - This one got a little wierd.http://i46.tinypic.com/xc518l.png)
Jack Slater (Last Action Hero)

He had no data on:

Sizemore Rockwell

It got Bender, Samantha from Bewitched, and Elminster so far. The wife and I are going to mess it a bit more later.

Try and Try as I might, I cannot get it to guess the one time appearance character Little Rock of Horrors from The Grim Adventures of Billy and Mandy.

Woops computer lag posted that twice, so here's an update.

It got:
The Ninja Turtles
Casey Jones
Mrs. McClusky (Desperate Housewives)
Bluto (Popeye)

Stumped it with:
The teacher of Lynette's kids (Desperate Housewives)
Coma Guy (House)

He's gotten a couple I'm surprised he got, considering his questions weren't really leading directly into the characters. For example, he got Char Aznable (Mobile Suit Gundam), Kamille Bidan (Mobile Suit Zeta Gundam), and Chrno (Chrono Crusade) all on question 20, despite never really narrowing it down too well.

Also managed to trigger my Gundam Nerdrage function when he claimed I was thinking of the Strike Freedom instead of Wing Gundam.

Things he didn't get, even after 40 questions:
Hot Ice Hilda (Outlaw Star)
Brad Swaile (Canadian Voice Actor)

I'mma keep trying, see what else he'll get.

He guessed Snow Miser instead of Richard from Looking for Group. That got a chuckle out of me.

This time I only went with "obscure" (well .. no..not THAT obscure) characters and it got them all wrong.
Here's the list:
Arnis
Judex
Wolfskin
Empowered
Ninjette
King Steve
Pamila
Phil
Ulysses 31
Lil mac
Ness
Ichi the killer
It also got all of the 5 cadillac cats wrong