Played by: Jack Nicholson

Before the 2005 Brad Pitt/Angelina Jolie flick Mr. and Mrs. Smith mishandled a similar type of plot, Prizzi’s Honor revolved around two assassin’s (Jack Nicholson and Kathleen Turner) who fall in love after being hired to kill each other. It was a supremely dark comedy that saw Nicholson seeming just as comfortable with marrying his would-be killer as he is with whacking her himself.

Nicholson doesn’t land on this list because of the way he handles a gun or the grisly way he takes out his targets. He’s here because of how he turned the hitman character type on its head with this role. Prizzi’s Honor is an expertly done dark comedy, and the way Nicholson brought a nonchalant attitude towards the business of murder shouldn’t be missed by fans of the actor.