Bond: “Tell me, which lunatic asylum did you get out of?
Grant: Don’t make it tougher on yourself, Mr Bond.”
SPECTRE’s ultimate killing machine, Red Grant is a convicted murderer who escaped from Dartmoor Prison and was recruited by Blofeld’s terror organisation. Grant, whose preferred method of murder after donning a pair of black gloves is to garrotte his vicim with a wire hidden in his watch - is selected by Rosa Klebb to eliminate Bond.
Fate: Stabbed and garrotted by Bond with his own wire on board the Orient Express.
The Actor: The Lancashire-born ex-teacher enjoyed a number of high-profile roles after Bond. He played an obsessed panzer officer in The Battle of the Bulge, a young Henry VII in A Man for all Seasons, a mobster in The Sting and shark-obsessed fisherman Quint in Jaws. Married three times, Shaw died aged 51 of a heart attack at the wheel of his car while driving in Ireland with his wife and young son. A Wetherspoons pub in his hometown honours him.