Who would it be? I would personally pick Wheatley from Portal 2. While kinda a screw-up, he's frickin hilarious.
Edit: Just to clarify, I meant like an artificial intelligence, a machine.
Edit: Cortana seems to be the favorite here (no surprise).
-
Junko enoshima from dangon ronpa 2. We'd be spreading despair EVERYWHERE! Plus shes [i]f[/i]ucking hot