Update:
Ada Wong (Resident Evil)
*Agent 47 (Hitman)
*Agent Smith (The Matrix)
Altaïr Ibn-La'Ahad (Assassin's Creed)
*Anton Chigurgh (No Country for Old Men)
Assassin (Fate/Stay Night)
Bad Girl (No More Heroes)
*Beatrix Kiddo/The Bride (Kill Bill)
Bullseye (Marvel comics)
Cammy (Street Fighter)
*Cigarette-Smoking Man (The X-Files)
*Combustion Man (Avatar)
Deadshot (DC Comics)
Dexter Morgan (Dexter)
*Ezio Auditore da Firenze (Assassin's Creed)
*Gray Fox (Metal Gear)
Henry Cooldown (No More Heroes)
*Himura Kenshin (Rurouni Kenshin)
HK-47 (Star Wars: Knights of the Old Republic)
*Jaffar (Fire Emblem 7)
*James Bond (James Bond series)
Jason Bourne (Bourne series)
*Kaku (One Piece)
*Kimmy Howell (No More Heroes)
Kitana (Mortal Kombat)
*Legault (Fire Emblem 7)
Leon (Leon The Professional)
*Light Yagami (Death Note)
*Lloyd Reed (Fire Emblem 7)
*Marluxia (Kingdom Hearts)
Mercenary Tao (Dragonball)
*Mystique (Marvel comics)
Nikita (La Femme Nikita)
Oddjob (Goldfinger)
O-Ren Ishii (Kill Bill)
*Puss in Boots (Shrek)
Psylocke (Marvel Comics)
*Sagiri (Suikoden V)
*Saito Hajime (Rurouni Kenshin)
Sara (Samurai Champloo)
*Scar (Full Metal Alchemist)
Scorpion (Mortal Kombat)
*Seta Soujiro (Rurouni Kenshin)
*Shadow (Final Fantasy VI)
*Shigure (Suikoden V)
*Shiki Nanaya (Melty Blood)
T-1000 (Terminator 2)
Terminator (Terminator)
*Thane Krios (Mass Effect)
*Tommy Vercetti (Grand Theft Auto: Vice City)
*Travis Touchdown (No More Heroes)
Ulquiorra Cifer (Bleach)
Vega (Street Fighter)
*Vicious (Cowboy Bebop)
*Volke (Fire Emblem 9/10)
Wolverine (Marvel comics)
*Zabuza (Naruto)
Zeratul (Starcraft)
*Zevran Arainai (Dragon Age: Origins)
--
Still smilin'
:>