Update:
Agent Smith (The Matrix)
Allied Mastercomputer (I Have No Mouth, And I Must Scream)
Alpha 5 (Power Rangers)
Aradiabot (Homestuck)
Ash (Alien)
Bass (Mega Man)
Bishop (Aliens)
Blackarachnia (Beast Wars)
Bomberman (Bomberman)
Brainiac (DC Comics)
Bumblebee (Transformers G1)
C-3PO (Star Wars)
Cait Sith (Final Fantasy VII)
Calculon (Futurama)
Caprica Six (Battlestar Galactica)
Cheetor (Beast Wars)
Clank (Ratchet & Clank)
Cortana (Halo)
Crow T. Robot (Mystery Science Theater 3000)
Cyrax (Mortal Kombat)
Data (Star Trek: The Next Generation)
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)
Gadget Z (Suikoden III)
Gato (Chrono Trigger)
GlaDOS (Portal)
Grimlock (Transformers G1)
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)
Johnny 5 (Short Circuit)
Machinedramon (Digimon)
Megatron (Transformers G1)
Melfina (Outlaw Star)
Miku Hatsune (Vocaloid)
Motoko Kusanagi (Ghost in the Shell)
Norm (Phineas and Ferb)
Optimus Prime (Transformers G1)
Porygon (Pokemon)
Proto Man (Mega Man)
R2-D2 (Star Wars)
Rin Kagamine (Vocaloid)
ROB (Nintendo)
Robot Devil (Futurama)
Robot Santa (Futurama)
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)
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)
Wheately (Portal 2)
Wren (Phantasy Star IV)
X (Mega Man X)
X-ATM092 (Final Fantasy VIII)
Zero (Mega Man X)
--
Still smilin'
:>