Appeared In: From Russia with Love (1963)
Played By: Robert Shaw
Diabolical Weapon: Pistol
Killed By: James Bond strangulation

In an attempt to avenge the death of Dr. No, Red Grant is sent by SPECTRE to assassinate Bond. He begins by deceiving 007 into almost handing over the Lektor encoding device to the evil organization, but Bond soon catches on and the two battle aboard a train. To put it mildly, things don’t quite work out for ol’ Red. Even in death he’s remembered as one of the best henchmen of Bond’s early years. Robert Shaw perfectly mixed menacing action with a cold, calm demeanor to truly give us the creeps whenever he was on screen.