Update:
Agent Smith (The Matrix)
Allied Mastercomputer (I Have No Mouth, And I Must Scream)
Alpha 5 (Power Rangers)
Ash (Alien)
Bass (Mega Man)
Bender Bending Rodriguez (Futurama)
Bishop (Aliens)
Blackarachnia (Beast Wars)
Brainiac (DC Comics)
Bumblebee (Transformers G1)
C-3PO (Star Wars)
Cait Sith (Final Fantasy VII)
Calculon (Futurama)
Cheetor (Beast Wars)
Clank (Ratchet & Clank)
Cortana (Halo)
Cyrax (Mortal Kombat)
David (Prometheus)
Demi (Phantasy Star IV)
Different Turret (Portal 2)
Dinobot (Beastwars)
Dog (Half-Life 2)
E-102 Gamma (Sonic Adventure)
Emeralda Kasim (Xenogears)
Gato (Chrono Trigger)
Grimlock (Transformers G1)
Grobyc (Chrono Cross)
HAL 9000 (2001: A Space Odyssey)
Harbinger (Mass Effect)
HK-47 (Star Wars: Knights of the Old Republic)
The Iron Giant (The Iron Giant)
Jinzo (Yugioh)
KOS-MOS (Xenosaga)
Machinedramon (Digimon)
Marvin (Hitchhiker's Guide to the Galaxy)
Mega Man (Mega Man)
Megatron (Transformers G1)
Melfina (Outlaw Star)
Motoko Kusanagi (Ghost in the Shell)
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 Santa (Futurama)
Sektor (Mortal Kombat)
Sentinel (X-Men)
Sharon 'Athena' Agathon (Battlestar Galactica)
Smoke (Mortal Kombat)
Starscream (Transformers G1)
T.O.M. (Toonami)
T-1000 (Terminator 2)
T-Elos (Xenosaga)
T260G (SaGa Frontier)
T3-M4 (Star Wars: Knights of the Old Republic)
Terminator (Terminator)
Tio (Grandia 2)
Thursday (Disgaea)
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)
Yuki Nagato (Haruhi Suzumiya)
Zero (Mega Man X)
--
Still smilin'
:>