Update:
Agent Smith (The Matrix)
Ash (Alien)
Bass (Mega Man)
Brainiac (DC Comics)
Bumblebee (Transformers G1)
Cait Sith (Final Fantasy VII)
Calculon (Futurama)
Cortana (Halo)
Data (Star Trek: The Next Generation)
Demi (Phantasy Star IV)
Different Turret (Portal 2)
Dinobot (Beastwars)
The Doctor (Star Trek Voyager)
Emeralda Kasim (Xenogears)
Gadget Z (Suikoden III)
HAL 9000 (2001: A Space Odyssey)
Harbinger (Mass Effect)
The Iron Giant (The Iron Giant)
Megatron (Transformers G1)
Proto Man (Mega Man)
Rin Kagamine (Vocaloid)
ROB (Nintendo)
Sektor (Mortal Kombat)
Sentinel (X-Men)
T-1000 (Terminator 2)
T260G (SaGa Frontier)
Terminator (Terminator)
Tio (Grandia 2)
Tom Servo (Mystery Science Theater 3000)
Zero (Mega Man X)
--
Still smilin'
:>