Okay, this is awesome.
I started with a few easy ones, just to see how this thing worked.
It got Morrigan (Dragon age), Phillp J. Fry (Futurama) and John Marston (Red Dead Redemption) all easily, so now I'm gonna throw it a couple curve-balls...
Okay, he got Michael Bluth (Arrested Development) AND Doug Walker (That Guy with the Glasses)
I'm impressed.
EDIT-
Okay, it took him two tries to get Angry Joe (Angry Joe Show), but I have a feeling that was more my fault for not knowing too much about him.