3. Le Chiffre
The very first Bond rogue in Flemings novels, Le Chiffres creepy ruthlessness is carried over into his film incarnation in 2006s Casino Royale, as he struggles to make good on the money he owes to some truly scary employers by winning a high-stakes poker gamewith Bond as his opponent. Le Chiffre is a middle-man, rather than a master-criminal, which actually makes him more interesting than your garden-variety megalomaniac billionaire; you can sense his sweaty desperation, caught in a vice between British intelligence and some very unsavoury parties who are even more powerful than he is. Le Chiffre is in a hugely perilous position, playing a deadly game of brinkmanship as he struggles to placate his superiors and foil the British at the same time. Hes an incredibly dangerous man, backed into a corner and living on borrowed time, and that drives him to extreme lengths to make his money. These lengths include threatening the worlds greatest lover with
drawn-out castration, in a gruelling sequence in which Bond is terrifyingly vulnerable in a manner rarely seen on page or screen. In the end, Bond is only saved by the hand of fate in the form of Le Chiffres vengeful masters.