Update:
Agent Smith (The Matrix)
Allied Mastercomputer (I Have No Mouth, And I Must Scream)
Ash (Alien)
Bass (Mega Man)
Bender Bending Rodriguez (Futurama)
Bishop (Aliens)
Brainiac (DC Comics)
C-3PO (Star Wars)
Calculon (Futurama)
Caprica Six (Battlestar Galactica)
Chachamaru Karakuri (Negima)
Cheetor (Beast Wars)
Data (Star Trek: The Next Generation)
David (Prometheus)
Demi (Phantasy Star IV)
Dinobot (Beastwars)
The Doctor (Star Trek Voyager)
Dog (Half-Life 2))
EDI (Mass Effect)
Emeralda Kasim (Xenogears)
Gato (Chrono Trigger)
Grimlock (Transformers G1)
Grobyc (Chrono Cross)
HAL 9000 (2001: A Space Odyssey)
The Iron Giant (The Iron Giant)
Jinzo (Yugioh)
Machinedramon (Digimon)
Mecha-Streisand (South Park)
Mega Man (Mega Man)
Megatron (Transformers G1)
Optimus Prime (Transformers G1)
Porygon (Pokemon)
Proto Man (Mega Man)
R2-D2 (Star Wars)
Rin Kagamine (Vocaloid)
ROB (Nintendo)
Robo (Chrono Trigger)
Robo-Ky (Guilty Gear)
Robot (Lost in Space)
Robot Devil (Futurama)
Robot Santa (Futurama)
Rosie the Maid (The Jetsons)
Sektor (Mortal Kombat)
Sentinel (X-Men)
SHODAN (System Shock)
Sovereign (Mass Effect)
Starscream (Transformers G1)
T-1000 (Terminator 2)
T-Elos (Xenosaga)
T260G (SaGa Frontier)
Terminator (Terminator)
Thursday (Disgaea)
Tom Servo (Mystery Science Theater 3000)
Ultron (Marvel Comics)
The Vision (Marvel Comics)
WALL-E (Wall-E)
Wheately (Portal 2)
Wren (Phantasy Star IV)
X (Mega Man X)
X-ATM092 (Final Fantasy VIII)
Zero (Mega Man X)
--
Still smilin'
:>