12. Teddy KGB (Rounders)
In the gambling film Rounders which stars Matt Damon and Edward Norton, Teddy KGB is a high-stakes underground poker player who bankrupts our hero in the first act. And in addition to merely being a skillful gambler who takes Matt Damon for thousands (despite his obvious tell), he also supposedly has multiple mob ties. Teddy KGB uses his money and power to aid a character known as Grandma, who bought out The Worm's debt when he was released from prison. It's another attempt by the Russian degenerate to pour salt in the wound of Matt Damon's life.
Why We Can't Help But Love Him: Malkovich's insanely over the top Russian accent give the character a beautifully re-quotable quality, well-known by anyone who's ever frequented a home poker game.