Best Dressed Movie Gangsters

The Smoking Jacket asks, Who are The 10 most stylish fictional gangsters of all time??
The winners come from TV shows and movies of all genres and time periods.
Here we count down the top 5!

Ajax movie

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.

Alex Delarge

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.

Jules Winnfield

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.

The Joker

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.

The Godfather movie

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.

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