Update:
Ada Wong (Resident Evil)
Agent 47 (Hitman)
*Agent Smith (The Matrix)
*Alice Twilight (No More Heroes)
Altaïr Ibn-La'Ahad (Assassin's Creed)
*Anton Chigurgh (No Country for Old Men)
*Assassin (Fate/Stay Night)
*Beatrix Kiddo/The Bride (Kill Bill)
Boba Fett (Star Wars)
Bullseye (Marvel comics)
Cammy (Street Fighter)
*Cigarette-Smoking Man (The X-Files)
Deadpool (Marvel comics)
Deadshot (DC Comics)
Dexter Morgan (Dexter)
*Ezio Auditore da Firenze (Assassin's Creed)
Gogo Yubari (Kill Bill)
Gray Fox (Metal Gear)
Henry Cooldown (No More Heroes)
HK-47 (Star Wars: Knights of the Old Republic)
*Jaffar (Fire Emblem 7)
James Bond (James Bond series)
Jason Bourne (Bourne series)
Jeego (Ghost Trick)
Kaku (One Piece)
*Kitana (Mortal Kombat)
Legault (Fire Emblem 7)
*Leon (Leon The Professional)
*Letz Shake (No More Heroes)
*Light Yagami (Death Note)
*Linus Reed (Fire Emblem 7)
*Lloyd Reed (Fire Emblem 7)
Mercenary Tao (Dragonball)
Mystique (Marvel comics)
Nikita (La Femme Nikita)
*Oddjob (Goldfinger)
O-Ren Ishii (Kill Bill)
*Paul Kellerman (Prison Break)
*Puss in Boots (Shrek)
Psylocke (Marvel Comics)
Sagiri (Suikoden V)
*Saito Hajime (Rurouni Kenshin)
Sara (Samurai Champloo)
*Scar (Full Metal Alchemist)
Scorpion (Mortal Kombat)
*Shadow (Final Fantasy VI)
Shigure (Suikoden V)
*Shiki Nanaya (Melty Blood)
*Strider Hiryu (Strider)
T-1000 (Terminator 2)
Terminator (Terminator)
*Thane Krios (Mass Effect)
Tommy Vercetti (Grand Theft Auto: Vice City)
*Tira (Soul Calibur)
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)
--
Still smilin'
:>