5. Le Chiffre (Casino Royale)
MGMLe Chiffre is Casino Royale's financier of international terrorism who has to play a high stakes game of poker with Bond after losing the Quantum criminal organisation's money in a stock deal he planned to manipulate through his ability to orchestrate terror attacks. The original Bond villain in the novels, we had to wait until 2006 to see him in an official Bond movie - although Orson Wells played him in the spoof 1960s adaptation of the novel.
Why He's So Stupid Le Chiffre suffers from that common Bond villain disease - over-confidence. Taking on two secret agents (Bond's CIA pal Felix Leiter being the other) in a game of high stakes poker isn't the smartest move for a man who they know to be behind international terrorism. Given the fact that it's hardly unknown for secret agencies to conduct assassinations of wanted terrorists, its a wonder that it was Bond who almost got killed at their poker game, and not Le Chiffre.
Dumbest Moment Undoubtedly his homo-erotic torture of Bond, featuring an unrelenting assault on 007's man parts. Eventually realises that he can play off Bond's affection for Vesper Lynd, but it's too late - Quantum have decided that they no longer trust Le Chiffre, making him very dispensable.