The 15 Most Stylish Hitmen

Contract killing may be an odd job, but it's still a professional field and as such, the talents of a would-be assassin are only as desirable as his presentation allows. You wouldn't trust a scrubbish dude in sweat pants with taking out your worst enemies.

In honor of Brad Pitt's latest role as Jackie Cogan, the leather clad hitman and protagonist of Killing Them Softly, out today, Complex has listed the freshest killers to ever do it. That's across all mediums: video games, comic books, film, even real life. Toast to the assassins who know how to kill in a classic suit, or the style innovaors who tried and succeeded for something flashier. Read on for The 15 Most Stylish Assassins.

Written by Frazier Tharpe (@The_SummerMan)

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Appears In: Sharky's Machine
Portrayed By: Henry Silva

Mob hitter Billy Score may be a drug fiend but at least his style senses haven't been dulled, as he goes in for the Business Casual Killer's favorite, the dark trench.

Appears In: The Spongebob Squarepants Movie
Voiced by: Alec Baldwin

Plankton's hired gun, or rather, boot, bucks all conventional hitman fashion staples and traditions. He looks like he'd have an easier time fitting in amongst the Sons of Anarchy over the League of Assassins, and for that he is a style innovator worthy of recognition. Dennis succeeds at the biker steez on his own merit though, with dope accessories like the one-hand spiked glove, skull belt, and necklace knife.

Appears In: The Man With the Golden Gun
Portrayed By: Christopher Lee

For a million dollars a hit, the swag better come correct. In fact, with that kind of money we half expected Scaramanga to dress loud and extravagantly but instead he keeps his suits and island wear decidedly classic and casual, putting all his extravagance into his main accessory instead: the infamous golden gun, which toes the line between gaudy and dope perfectly. Midget henchman Nick Nack, however? Accessory fail.

Appeared in: Real Life

Woody Harrelson's estranged father was a big time mob-hitter before getting sentenced with two-life terms for committing the first murder of a federal judge in the 20th century. In addition to that resume highlight, and being father to one of the best character actors of our generation, Charles was quite the sharp dresser as well. When you've got historic kills to your name, stepping out in three piece suits and the like is basically a must.

Appears In: Hitman video game series
Voiced By: David Bateson

Agent 47 trademarks in banality and straightforwardness, so he fittingly sticks to the stock assassin's uniform: black suit and black leather OJ isotoners. But it is classic for a reason, and we can't really fault him when he pulls it off so well. The billowing, bright red tie is an admirable attempt at actual effort.

Appears In: Day of the Jackal
Portrayed By: Edward Fox

To match his extravagant methods—disguising his rifle as a crutch, various disguises—The Jackal takes commendable style risks. We don't care that his ultimate assasination attempt failed, anybody that dares try his hand at the ascot (no matter how English he is) and succeeds is a winner in our book.

Appears In: The Matador
Portrayed By: Pierce Brosnan

The aging, spiritually adrift assassin takes the mid-life crisis swag and actually makes it work, in a way that only Pierce Brosnan could. From the Burt Reynolds stache to his outerwear game, everything about Julian Noble's steez should be corny, but he pulls it off. We can't think of any dude that could pull off suede jackets and high-collar leathers like he does. Maybe the sniper rifle helps?

Appears In: DC Comics' Hitman; other DC titles

Contract killer Tommy Monaghan, infamous for taking on supernatural targets, shamelessly robs Daria's steez and makes it his own. That long green trench coat paired with thick-soled military boots maybe a grunge staple, but the fact that he pegs his pants and pairs it all with leather gloves and stark black sunglasses shows that he knows what he's doing.

Appear In: Pulp Fiction
Portrayed By: John Travolta and Samuel L. Jackson

The chillest, most conversational hitmen to ever do it go full Blues Brothers for their appearance. Instead of coming off as plain, the classic suit instead reflects their cool, calm, collected look perfectly and we get the sense from their sheer discomfort in civilian clothes during "The Bonnie Situation" that their enforcer uniforms are really more like a second skin that they rock even when off the job.

Appears In: Léon: the Professional
Portrayed By: Jean Reno

In addition to being an icon for the cinematic hitman (or "cleaner" as he would prefer) archetype in method and presentation, Léon is a figure as well for his effortless wintertime New York style execution, from the perfect beanie fit accentuated by the bold choice round sunglasses, to the hipsterish suspenders. The perfect look for strolling around Little Italy.

Appears In: Collateral
Portrayed By: Tom Cruise

For Collateral Tom Cruise adopted his freshest look on-screen and off to date, with a sharp wolf-grey 'do and crisp suit to match. The commanding contract killer looks more like a power broker, accented by the sound, contemporary decision to go tie-less.

Appears In: Le Samouraï
Portrayed By: Alain Delon

The minimalist, detail-obsessed killer Jef Costello keeps it European and sparingly stylish with a fresh and clean trench coat and matching fedora. It's casual and quiet, but so French in its execution that you half expect to see him posted up at a cafe sipping espresso instead of merking dudes.

Appears In: Road to Perdition
Portrayed By: Jude Law

The photography obsessed assassin mostly adheres to the hitman steez script within Depression-era parameters, but strays outside of the box with his bold choice of bowler instead of the favored fedora.

Appears In: Prizzi's Honor
Portrayed By: Jack Nicholson

Unless the role specifically calls for him to turn his swag down if not all the way off (as opposed to all the way up) Jack Nicholson's characters usually stunt out of control, and mob shooter Charley Partanna is no different. Prizzi's Honor is basically Jack's Casino moment, as he pulls off vibrant, flashy looks, similar to De Niro's Ace Rothstein, that anybody else would fail spectacularly at, peaking with the banana-yellow blazer seen above.

Appears In: The Killers
Portrayed By: Lee Marvin

As professional hitman Charlie Strom, Lee Marvin stunts through his contract kills with his crisp fedora and shades like he's posing for GQ, even imparting the fresh code as a de facto uniform to his young accomplice Lee.