1. Donald 'Red' Grant (Robert Shaw - From Russia With Love)
Cold, intelligent and ruthless, Red Grant acts as the perfect foil to Bond through From Russia With Love, with the two men differentiated only by the fact that Grant is a homicidal murderer in the employment of the criminal organisation SPECTRE, tasked with killing 007 in revenge for his killing of their operative, Dr. No. Effortlessly killing two of Bond's allies, he comes dangerously close to killing the man himself, who is saved, for the first of many times, by the concealed gadgets at his disposal. The character, short on words and physically imposing, would become an archetype for numerous other henchmen throughout the series, ranging from Necros in The Living Daylights to Herr Stamper from Tomorrow Never Dies, though none would ever come close to matching the menace of the original.