The 10 Most Stylish Fictional Gangsters of All Time

Let’s face it—fictional gangsters are more fun than real ones. Fictional gangsters get into prolonged shootouts that destroy half of city hall. Fictional gangsters have dinner with the chief of police and then sleep with his wife. Fictional gangsters never run out of bullets, whores, exotic tiger-pets or favors to grant on the day of their daughter’s wedding.
These factors mean made-up gangland is not only way more fun than
real gangland, it also looks undeniably cooler. Exotic villas, exclusive night clubs, hollowed-out volcanoes—real gangsters and their dingy basements just can’t compete. Nor can their fashion sense compete with that of their fictional counterparts, many of whom have become pop culture fashion staples. Here’s a list of the 10 most stylish fictional gangsters of all time.
10 Michael Sullivan (Road to Perdition)

Michael Sullivan is the kind of man who’d rather be caught dead than do his job without looking formal and dapper. His job, ironically, is killing people. When he’s on his way to work wearing a suit, overcoat and a fedora hat, you might mistake him for a banker who is just paranoid enough to carry a Tommy gun under his arm.
9 Mr. Blonde (Reservoir Dogs)

Mr. Blonde looks exactly like everybody else in Joe Cabot’s crew, but nobody can touch his penchant for psychotic badassery, which is why he’s on the list. Fun fact: The budget for Reservoir Dogs was so low that all the actors mostly provided their own wardrobe. This means we can all thank Michael Madsen for making Blonde look like the FBI agent you never, ever want interrogating you.
8 Paulie Walnuts (The Sopranos)

As the most senior member—and last man standing—of the Soprano crew, Paulie is a Jersey gangster pastiche of past & present. He’s equally as comfortable and unwilling to tolerate your bullshit in a Fila track suit at Satriale’s Meat Market as he is at a sit down wearing a Pierre Cardin wool suit.
7 Tony Montana (Scarface)

Tony proved that you didn’t have to look like a glam-metal freak do a bunch of cool ’80s-related activities, like snorting a molehill of high quality yeyo and shooting your best friend. All you needed was a cache of polyester disco suits with the shirts halfway unbuttoned.
6 Reese Feldman (Starsky and Hutch)

There was a time before the biker guy from The Village People when horseshoe mustaches were the shit, as proved by Reese Feldman. Reese is man enough to wear pink at his daughter’s Bat Mitzvah and nut-hugging swimming trunks on his boat while he executes some poor fool.
5 Ajax (The Warriors)

Ajax is some sort of cross between a Wild West gunslinger and a modern-day WWE heel. Like the other Warriors, he wears a brown leather vest and keeps the shrunken, defeated testicles of the Baseball Furies in his pants pockets. Ajax hearkens back to a magical time—the late ’70s, to be exact—when gangs preferred rumbling in matching outfits to pussy-ass drive-bys.
4 Alex Delarge (A Clockwork Orange)

Although it’s been almost 40 years since A Clockwork Orange forever sullied “Singing in the Rain” and scared the crumpets out of Great Britain, Delarge’s droog uniform—white long-sleeve shirt, white pants, black combat boots, black Belfry top hat, some kind of molded nut-protector— can still be seen come Halloween time, usually by the guy looking to beat the shit out of you before he takes your girlfriend.
3 Jules Winnfield (Pulp Fiction)

In the case of Jules Winfield, the whole package must be appreciated as a part of his style, which includes the jheri curled afro—the only time in the history of ever that a jheri curl has managed to look cool—and the combination mutton-chopped, fu Manchu facial hair. Like Mr. Blonde, Jules is suave enough in his black suit to be mistaken for an insurance before he lays his vengeance upon thee.
2 The Joker (The Dark Knight)

Heath Ledger’s Joker incarnation was both the worst and best thing ever to happen to clowns—Patrick Bateman meets Bozo, if Bozo had spent time in Chino instead of clown college.
1 Michael Corleone (The Godfather)

Vito Corleone may be the original gangster, but nobody made fratricide more stylish than prodigal son Michael. He did business at all times impeccably tailored form head to toe. His three-piece gangster suits are every bit a part of his lore as a tunic would be to a Roman emperor.