Update:
Agent Smith (The Matrix)
Alpha 5 (Power Rangers)
Ash (Alien)
Bass (Mega Man)
Bishop (Aliens)
Blackarachnia (Beast Wars)
Brainiac (DC Comics)
Bumblebee (Transformers G1)
Cait Sith (Final Fantasy VII)
Calculon (Futurama)
Cortana (Halo)
Cyrax (Mortal Kombat)
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)
Machinedramon (Digimon)
Megatron (Transformers G1)
Porygon (Pokemon)
Proto Man (Mega Man)
Rin Kagamine (Vocaloid)
ROB (Nintendo)
Robot Santa (Futurama)
Sektor (Mortal Kombat)
Sentinel (X-Men)
Sovereign (Mass Effect)
Starscream (Transformers G1)
T-1000 (Terminator 2)
T3-M4 (Star Wars: Knights of the Old Republic)
Terminator (Terminator)
Tio (Grandia 2)
Tom Servo (Mystery Science Theater 3000)
The Vision (Marvel Comics)
Zero (Mega Man X)
--
Still smilin'
:>