The hitman is one of the great character types in all of film. These amoral killers are in the business of professional murder, which demands a healthy blend of ruthlessness and the spirit of an entrepreneur. Most people like to claim that you can’t put a price on a human life—well, these folks share a different opinion.

Usually working for someone with deep pockets, contract killers take meticulous care with their appearance and the method in which they dispose of targets. Let’s face it, no hitman can afford to be sloppy, or else their career won’t likely survive the first job. That means whoever takes one of these roles has to be damn good at it.

This Friday marks another proud addition to the paid murderer on-screen pantheon with the first-rate crime flick Killing Them Softly, in which Brad Pitt plays Jackie Cogan, a hired gun working for the mob. Before you go off to see the film (which we highly recommend that you do), take a look back at some of his contemporaries in our list of The 25 Coolest Hitmen In Movies.

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Written by Jason Serafino (serafinoj1)