The occupation itself, a man who sets himself up as a professional judge of life and death is naturally perfect for delving into certain existential dilemmas, most often; disconnection, the bonds that exist in and out of society, the nature and weight of loneliness, and guilt and consequence catching up with you. These are themes we can all relate to, but the hit man shows them in a black and white that most of us don't have, even as he tries to ignore such definition and live in his own grey area.
Other characters, such as cops, mob bosses, freelance psychopaths and even average people out for revenge or self defense, may have to deal with killing, but not in the same way. The Hollywood hit man is typically, the "blue collar" judge, a working man not above his own rules. Even the most skilled often end up dead themselves as a known risk of the occupation. These characters at the edge of life and death naturally present a unique viewpoint to look at life.
These movies usually deal with "the last job." The job doesn't have to be a "job" either, many times it's the fact that the last kill is personal, that signals the hit man's unravelling. In these worlds, any emotion is the enemy, necessary to have any depth of life, but fatal to someone using emotional distance to survive. Usually the guilt of many years of taking lives catches up to the killer and he changes before he dies (or fails to change.) Change is almost always featured and although it most certainly means death, the hit man, like many of us can't help but wrestle with thoughts of the life he doesn't have. He eventually takes the risk, often accepting, fatalistically, that at least death is a change that can happen.
So here are my top ten at this moment. There are many others that could have made my list. Feel free to point out your own favorites in the comments.
8. Jules Winnfield: (Samuel L. Jackson)Pulp Fiction
7. Frankie Bono: (Allen Baron) Blast of Silence
Frankie Bono is an orphan who grew into a hired killer so disconnected from the world he doesn't remember how to deal with social situations anymore. His latest hit is set in New York during the Christmas season, the worst time of year for the lonely. Frankie is so silent, we need narration to get into his head. Frankie makes some mistakes, has to deal with an attempted blackmailing by a gun dealer and even more difficult, seeing a woman he used to know and attending a Christmas Party, breaking his own rules about attachment only to get shut down. Once his loneliness is let out we know it can't go well for Frankie. And we wonder if he could ever have what he feels he's missing. The narrator says of Frankie in the closing:
"God moves in mysterious ways," they said. Maybe he is on your side, the way it all worked out. Remembering other Christmases, wishing for something, something important, something special. And this is it, baby boy Frankie Bono. You're alone now. All alone. The scream is dead. There's no pain. You're home again, back in the cold, black silence. "
6. Joey Cusack/Tom Stall (Viggo Mortensen): A History of Violence
5. O. ( Takshi Sorimachi) Full Time Killer
4. Ghost Dog (Forrest Whitaker) Ghost Dog: The Way of the Samurai
3.Charlie Strom (Lee Marvin) The Killers
We see right away that Charlie Strom is a cold blooded killer capable of anything when he has a job to do. He thinks nothing of intimidating the principal at a school for the blind to get the whereabouts of his target Johnny North (John Cassavetes) What he doesn't count on is Johnny accepting his fate without any fuss, even covering for Charlie and his partner so they can get him alone in his room to kill him. While not sympathetic, Charlie is puzzled and needs to know more. They investigate and get Johnny's life story, revealing a love triangle hinging on a girl, Sheila (Angie Dickinson) which put Johnny up against a mob boss, Jack Browning (Ronald Reagan) and a million dollars floating around somewhere. Charlie doesn't mind beating Sheila and dangling her from seven stories up to get the truth. Finding that Sheila and Jack Browning viciously double crossed Johnny, Charlie realizes that the Johnny North didn't fight his death because he was already dead in his own mind. Deciding that Johnny deserves some payback, Charlie assigns himself a job, and knowing that Charlie is Lee Marvin, you can bet it isn't good for Sheila or Jack Browning.
2. Jef Costello (Alain Delon) Le Samourai