Hannibal Lechter, The Silence of the Lambs

We start off our countdown with the most dapper cannibal to ever grace the silver screen. Hannibal Lechter played brilliantly by Sir Anthony Hopkins is not only a cold-blooded, methodical and brilliant sociopath, but is it also a cold-blooded methodical and brilliant sociopath with panache.

The Corleone Family, The Godfather Saga

Never take sides against the family and never show up with a stitch out of place. The Corleone family may have been involved in many illicit criminal activities including murder and racketeering, however they did it looking better than anybody in the room, politicians included.

Frank Lucas, American Gangster

Leave it to Denzel Washington to make a criminal mastermind look like a successful businessman. His character Frank Lucas in the great film American Gangster show that once again that Washington is one of America’s great leading men whether he’s the villain OR hero.

Clyde Barrow, Bonnie and Clyde

THEY ROBBED BANKS. They also looked amazing doing it. The real-life Clyde Barrow may not have looked at like Warren Beatty, but the film definitely added to the mythos of America’s most notorious lovers/criminals.

Mr. Pink, Mr. White, et. al., Reservoir Dogs

We’ve all pretended to be the dogs at one point or another. We all own black suits and ties. It doesn’t take a rocket scientist to know that any man at time or another has probably wish he was Mr. Pink or Mr. White.

Robert “Rusty” Ryan, Ocean’s Eleven

It’s easy to look stylish when Brad Pitt is playing the role and Rusty Ryan is no exception. Even though he was eating throughout the entire film, Rusty was always the #1 of the 11 when it came to fashion and style.

Jack Carter, Get Carter

Three words: Michael Fucking Caine.

Vincent, Collateral

Tom Cruise playing the villain was something new for us to see when Collateral came out. It was also Tom Cruise’s most stylish role since Vanilla Sky. The gray suit on gray hair somehow made it perfect. We look forward to the day when we can pull off that look ourselves.

Tie: Big Chris, Lock, Stock, & Two Smoking Barrels/Bullet-Tooth Tony, Snatch

Leather jackets. Three piece suits. Guns. Guy Ritchie’s seedy London underbelly would not be complete without Vinnie Jones and has similar yet distinct roles as Big Chris and Bullet Tooth Tony in these bookend films from the English filmmaker. Jones, a former soccer player, was an absolute natural as the hard gangster in both installments, but brought an effortless British charm to the films. An inspiration to all hitmen

Henry Hill, Goodfellas

Ray Liotta didn’t just wear the suits and comb his hair just so for this Scorcese classic, he inhabited the role of Henry Hill and everything that came with it, not least of which was the swagger to do so.