Update:
Agent Smith (The Matrix)
Ash (Alien)
Bass (Mega Man)
Bender Bending Rodriguez (Futurama)
Bishop (Aliens)
Brainiac (DC Comics)
Bumblebee (Transformers G1)
C-3PO (Star Wars)
Cait Sith (Final Fantasy VII)
Calculon (Futurama)
Cheetor (Beast Wars)
Cortana (Halo)
Cyrax (Mortal Kombat)
Data (Star Trek: The Next Generation)
David (Prometheus)
Demi (Phantasy Star IV)
Different Turret (Portal 2)
Dinobot (Beastwars)
The Doctor (Star Trek Voyager)
Dog (Half-Life 2)
E-102 Gamma (Sonic Adventure)
EDI (Mass Effect)
Emeralda Kasim (Xenogears)
Grimlock (Transformers G1)
Grobyc (Chrono Cross)
HK-47 (Star Wars: Knights of the Old Republic)
The Iron Giant (The Iron Giant)
Jinzo (Yugioh)
Marvin (Hitchhiker's Guide to the Galaxy)
Megatron (Transformers G1)
Melfina (Outlaw Star)
Metal Sonic (Sonic)
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 Santa (Futurama)
Rosie the Maid (The Jetsons)
Sektor (Mortal Kombat)
Sentinel (X-Men)
Sharon 'Athena' Agathon (Battlestar Galactica)
Sovereign (Mass Effect)
Starscream (Transformers G1)
T-1000 (Terminator 2)
T-Elos (Xenosaga)
T260G (SaGa Frontier)
T3-M4 (Star Wars: Knights of the Old Republic)
Terminator (Terminator)
Tio (Grandia 2)
Tom Servo (Mystery Science Theater 3000)
Ultron (Marvel Comics)
The Vision (Marvel Comics)
WALL-E (Wall-E)
Wren (Phantasy Star IV)
X (Mega Man X)
Zero (Mega Man X)
--
Still smilin'
:>