Okay, I found out about this website from another forum and at the time I was addicted to it for 2 or 3 days straight. Basically it's a 20 questions type of thing to guess a character you're thinking of, and he gets to guess as many times as he wants within 40 questions in total. He's actually really good, and got some very obscure video game characters right on the first try for me.

http://us.akinator.com/#

When it asks for name age etc. just put something random, because it doesn't really matter and doesn't send to emails or anything.

he's awesome. just got warchief Thrall right 

He got Dave Grohl in 14 questions.. It's almost eerie.

It failed to get the main character of Tengai Makyou 2:  卍MARU


edit: It got Arle (puyo puyo) after all 40 questions
edit 2: it got Adol (Ys) and failed to get Rick (splatterhouse)
edit 3: failed to get Tex Murphy of the series of the same name

People I didn't expect him to get but he did:
Laharl from Disgaea.
Rico from Xenogears.
Nash from Lunar Silver Star Story Complete.
The main character from Double Dragon.
Quote and Curly Brace from Cave Story.
Cyberdwarf from Barkley Shut Up and Jam: Gaiden.
Isaac from Lost Magic.
Arthur from Ghouls 'n Ghosts.
Terra from FF6.
Mr. Horse from Ren and Stimpy.

People he didn't get:
Kyle from Lunar Silver Star Story Complete.
Luthor Huss from Warhammer.
The main character from Persona 3 (granted he has no name).
Bill Cavalier the Dungeon Bastard (a youtube person).
Sylvia from Viewtiful Joe.

I'm surprised he got Echo from Dollhouse, I'm going to have to think of a bunch of things to try now!