As troubling as the idea is of putting a price on murder, the fictional (and real-life) men and women who made careers based on doing just that have fascinated the public for years, and this week’s hitman drama Killing Them Softly proves the attraction is alive and well.

We thought we’d take this opportunity to look back at the hitmen who captured our attention (and box office dollars) over the years. As time goes by, more mob movies, gangster films, and even dark comedies continue to cast a hitman as the embodiment of cool, fear, or class.

But a select few made a more lasting impression; see if you agree with our list of the Top 10 Coolest Movie Hitmen.

“Every day, without fail, one should consider himself as dead. This is the substance of the Way of the Samurai. “

Not every hitman or hired gun has a code of honor to live by, but the titular hero of Ghost Dog (1999) takes things to a new level. Following the tradition of the Japanese samurai and the teachings of the Hagakure (‘The Book of Samurai’), Ghost Dog (Forest Whitaker) brings unprecedented ritual and wisdom to the role of a hired killer.

Motivated not by greed or bloodlust but duty to the mobster who saved his life, Ghost Dog spends his days in meditation and congregation with his homing pigeons. If that alone isn’t enough to prove he’s one of a kind, did we mention his preferred weapon is a katana? Maybe now you understand why it’s one of our favorite cult movies.

Ghost Dog’s weaponry isn’t the only thing that made a mob movie set in New Jersey feel fresh and original – but it didn’t hurt. Ghost Dog’s unique sense of life and death stole the show; after all, it’s one thing to eliminate a target, but to convince the target that dying would make one a greater warrior than trying to fight – that’s a gift.

“No women, no kids: that’s the rules.”

Anyone who knows hitmen knows Léon: The Professional (1994). Being known as ‘the professional’ gives an idea of how reliable a “cleaner” Leone ‘Léon’ Montana is for the New York City mob. True to his title, Léon does little else besides take out targets. That’s not a recipe for an incredibly interesting character, but all that changes when the man of few words receives an apprentice.

Taking an orphaned Matilda (Natalie Portman) under his wing, Jean Reno and a then-twelve year old Portman made a quirky, funny, and deeply troubling relationship work. The story of a friendless hitman teaching a young girl to follow in his footsteps is a hard sell for even modern audiences, but the film won over many skeptics by oozing style and featuring one of the greatest villains in movie history.

Director Luc Besson is synonymous with compelling action built around highly-trained killers, but as the passing years have proved, there is only one Léon. And paired with Portman – who our readers named as their favorite child performance ever – there’s nothing better.

“What? I should only kill people after I get to know them?”

With more and more films pursuing bigger budgets and bigger action, director Michael Mann went the opposite direction with Collateral (2004). And boy, did it pay off. Spawned from the mind of writer Stuart Beattie, who imagined a serial killer replacing him in his easy conversation with a cab driver, the full script stayed true to that sense of intimacy, minimal cast, and slow pace.

Jamie Foxx’s Oscar nomination as Max, the driver-turned-wheelman might imply that he was the shining star of the film. But what most surprised moviegoers was Tom Cruise, the quintessential leading man and heartthrob trading his smile and charisma for the grey hair of no-nonsense hitman, Vincent.

Portraying a killer that an audience can be terrified by, and even grow to like (until reminding them why he is to be feared, not trusted) is a difficult task for any actor. The bottom line: Vincent is one of the most chilling, determined, and convincing hitmen we’ve seen in recent years; the fact that Tom Cruise brought him to life only makes him more unforgettable.

“I shoot people for money…priests, children – you know, the usual.”

‘Neurotic’ and ‘guilt-ridden’ aren’t words usually used to describe guns for hire – but they do define Colin Farrell’s hitman from In Bruges (2008). Introduced to the hitman Ray (Farrell) and his partner shortly after a contract – Ray’s first – has gone horribly wrong, the decision to lay low in Bruges, Belgium is an unforgettable one for both Ray and the audience.

…It’s a unique getaway to say the least: drugs, (racist) dwarves, and even a tourist couple (from Canada no less) being beaten by a misinformed Ray, are all set against the medieval architecture of Bruges. Add the fact that it takes place amidst the caroling and decorations of Christmas, and the fever-dream mentality of large portions of the film becomes clear.

Besides Farrell turning in one of his best performances to date (winning a Golden Globe in the process) Ray is one of the few hitmen who possess none of the mysticism or preternatural skill usually attributed to the profession – yet his quirk and guilt endear him to the audience more than a murderer is usually capable of.

“Always trust a bank manager.”

It’s not every day that one of the greatest living actors decides to trade an Academy Award for a tommy gun, so when Tom Hanks stepped in to play mob hitman Michael Sullivan in Road to Perdition (2002), many took notice. Making a hitman the hero of any story is a risky move, but Michael Sullivan is the heart of the story as not just a mob enforcer, but a husband, a father, a Catholic, and a truly tortured soul.

Bolstered by Hanks’ and Paul Newman’s strong performances, Sullivan represents a rarity in the genre of hitman/gangster films – not a glorified figure of violence, but a historically accurate look at the type of crime many Irish immigrants were forced into in the early 20th Century. Sullivan’s dedication to his friends, family and oldest son was heart-breaking and relatable – a true rarity among gun-toting hoodlums.

Would the comic book adaptation have worked as well without Hanks? Fortunately, we didn’t have to find out.

“Charlie Chaplin once entered a Charlie Chaplin look-alike contest in Monte Carlo and came in third; that’s a story.”

His name is Goodkat, buy you can call him ‘Mr. Goodkat.’ From the moment Bruce Willis explained the intricacies of the ‘Kansas City Shuffle’ to one of his ill-fated victims, it was clear Lucky Number Slevin (2006) and Goodkat’s role would offer something a bit different from the norm.

Bruce Willis’ current tendency to play tough, threatening men of few words is a far cry from his most memorable role as Detective John McClane, but for Goodkat, the style was a perfect fit. A hitman who lets a handful of sentences suffice (until his guns were needed) more than balanced out Josh Hartnett’s mile-a-minute dialogue, and the discrepancy between the two made the final act even more impactful.

We won’t spoil the twist, but a hitman who can truly sit back and let a painfully-constructed plan come together – yet still be willing to get his hands dirty (although, not too dirty) is a rare thing; especially when he can still surprise you.

“Even a filthy beggar like that has got a protecting angel.”

For many, ‘spaghetti western’ is synonymous with names like Clint Eastwood and The Good, the Bad and the Ugly (1966). But we can’t forget the bad guys. The face of Lee Van Cleef is recognizable to any western fan as one of the genre’s most iconic villains – and no role more memorable as that of Angel Eyes (‘The Bad’), the gunslinger making good on two contracts at once.

It’s surprising to think of Van Cleef having enjoyed only small TV roles before director Sergio Leone, the creator of the ‘spaghetti western,’ tapped him to appear as a good-hearted military man in For A Few Dollars More (1965). For The Good, the Bad and the Ugly, Leone needed a villain; the rest is history.

It wasn’t necessarily Angel Eyes’ motivations that were most captivating, but the man himself. With his beady eyes (which Van Cleef later stated were “the best thing that ever happened to me”) squinting in the desert sun, the film ensured audiences would never forget Angel Eyes and Van Cleef’s lasting career as one of the most iconic villains the old west ever produced.

“I won’t tell you you can save yourself, because you can’t.”

Anton Chigurh is a no-brainer, as he proved single-handedly that the American southwest – even in the 1980s – was No Country For Old Men (2007). The Coen Brothers have proven their ability to write off-beat characters – even those who kidnap and kill for a price. But with Chigurh, they took depravity and unsettling dialogue to an extreme, and Javier Bardem made good on the writing.

Accepting money to take out targets for an organized crime syndicate is one thing, but killing innocent bystanders as some sort of exercise in fate or existentialism is the mark of a truly disturbed individual. There were no lines Chigurh wouldn’t cross, nobody deemed off-limits or exempt from his handiwork. And at his profession, he is thorough.

He even made the word ‘friendo’ an open threat. For that, we’re willing to forget his haircut. In fact, don’t even tell him we brought the hair up at all.

“I always leave one bullet, either for myself or for my enemy.”

John Woo’s name has become inextricably linked to Hong Kong action and over-the-top style since his rise to fame in the West – and the reasons why are on full display in The Killer (1989). Following leading man Ah Jong (Chow Yun Fat), a hitman compelled to care for and rehabilitate a young woman injured during one of his jobs, Woo crafted a hitman who was likable, while also deadly to those who deserved it.

The film doesn’t take long to rush headlong into bloody action, inspired fight choreography, and a deep connection between Ah Jong and the investigating detective – successful tropes that became commonplace in Woo’s future endeavors.

Ah Jong’s portrayal as a deadly but compassionate killer amidst overwhelming stylized violence led to a finished product which Quentin Tarantino and Robert Rodriguez would both name as an inspiration. The Killer also marks the first example of Woo’s love of doves on screen, which alone warrants its inclusion.

Jules: “I’ll just walk the earth. “
Vincent: “What’cha mean walk the earth? “
Jules: “You know, walk the earth, meet people… get into adventures. Like Caine from “Kung Fu.””

This pair needs no introduction, as Pulp Fiction (1994) guaranteed that director Quentin Tarantino, John Travolta and Samuel L. Jackson (among others) had long, strong careers ahead of them. As hitman in the employ of Marsellus Wallace, Jules Winnfield and Vincent Vega started with a discussion of hamburgers, and ended plastered on the wall of every college dorm.

With too many quotes and personal philosophies to name, the pair of verbose and deadly hitmen didn’t just prove that John Travolta could do more than talk to babies – they embodied the stylized violence and dialogue that would ultimately become Tarantino’s trademark.

There is no other hitman or duo that we would rather employ to get a difficult job done – provided we could come along for the ride.

Those are just a small sample of the many hitmen, contract killers, and those who take things to a new level of ‘assassinry.’

There are too many to name, so rather than produce a list of honorable mentions, we throw the floor open to you: What hitmen/hitwomen have left an indelible mark on your imagination? Was it their methods, or their personality?

We’ll see if Brad Pitt can add ‘Jackie Cogan’ to our list when Andrew Dominik’s Killing Them Softly hits a wide release. But as our Top 10 shows, he’s following some legendary characters.

Killing Them Softly is now in theaters.

Follow me on Twitter @andrew_dyce.