Twenty of the Toughest Fictional Movie Gangsters

Movie gangster or real gangster, it’s always been an allure for us in the public. Why? I think it’s pretty simple really. We’re always intrigued by people who don’t follow the rules. It doesn’t mean that we’ll go out and be gangsters, but for a couple hours we can imagine what a life like that might be like. And when the directors and actors get it right, you actually root for these criminals.

And these guys take form in all shapes and sizes, country of origin, and most importantly, willingness to do anything and everything for their cause. You won’t find anything from Goodfellas in here (because those guys are based on real people).

These are the 20 toughest fictional movie gangsters

The Godfather – Vito Corleone

Obviously you don’t start a list like this without the Godfather himself. Never has there been a bad guy portrayed in such a good light in cinema before. It’s amazing how much you root for this guy. Although I have to say I think De Niro playing a young Vito is a bit cooler than Brando. Brando’s character is a bit too old. Still though, a force.  He’ll go down in history as one of the most influential fictional gangsters of all-time with future movies modeling characters after him.

Nikolai – Eastern Promises

It doesn’t get tougher than that naked knife fight scene in the bathroom. Viggo shows his birthday suit and also kills a guy in the process. Plus the dude is a cop. He ends up staying mafia though. Highly tough.

Bricktop – Snatch

If I could understand half the words this guy was saying, I’d give him much more credit. Although feeding his victims to pigs was certainly an interesting move. Still though, Brad Pitt gets the best of him in the end.

Frank Costello – The Departed

I personally thought this was one of Nicholson’s better roles. And it gave great insight into the Irish Mafia (what a dumb sentence). My favorite line: “snort it till your numb.” He truly was a sadistic piece of work wasn’t he?

Lil Ze – City of God

Perhaps no one was more psycho than the character of Lil Ze in City of God. The guy shot up an entire motel before the age of 13. Then he goes on to take over practically all of the drug trade in the slums of Rio. The guy is an absolute machine. If you haven’t see City of God, then you must.

Alex De Large – Clockwork Orange

If you don’t think that Clockwork Orange classifies as a gangster movie then what in the world do you call Alex’s little group? A book club? Nope, that was a gang and Alex was the King of that gang.  De Large will go down as one of the most sinister characters to ever grace the silver screen.  He’s got a penchant for sex and violence as well as a thirst for trouble.  Nothing, not even shock treatment will take that away from him.

Sonny LoSpecchio – Bronx Tale

Inventor of the door test and king of the neighborhood, Sonny was both a role model and a man to fear. What a great movie Bronx Tale was. Sonny definitely made it better. When he took out that biker gang, that was the epitome of gangster.

Frank White – King of New York

Oh come on now. When you’re used in the lyrics of over 200 rap songs you know you have to have a large amount of street cred.

Michael Corleone -The Godfather

Second to Vito and first in our hearts is Michael Corleone. From goody two shoes solider to ruthless dictator, Corleone transforms before our eyes to become one of the most vicious gangsters that cinema has ever seen. Killing your own brother? Pretty gangster.

Big Chris – Lock Stock and Two Smoking Barrels

It doesn’t get much cooler than the gun scene. Remember? Big Chris uses the term “balls” and how they’re definitely shriveling up for his enemies because they’re carrying replica guns unlike his massive pistol. Plus the guy is carrying around his son the whole time. What a stud.

Michael Sullivan – Road to Perdition

Irish mob movies don’t get much better than Road to Perdition. And I never thought I’d ever say Tom Hanks was tough in anything, but come on. The man has the guts to come back and wipe out almost an entire mob by himself. He’s quiet.  He’s cool.  And he’s ridiculously awesome with a machine gun.  Plus he’s doing all of this alone.  Plus he teaches his son how to be the getaway driver.  Oh, and he sacrifices himself for his son.  Doesn’t get tougher than that.

Marsellus Wallace – Pulp Fiction

Possibly given some of the coolest lines in movie history, Marsellus is one gangster you do not want to mess with. If you do, “he’ll get medieval on your you know what”

Johnny Boy – Mean Streets

Robert De Niro getting two spots here. Most of you may not have seen Mean Streets but Johnny Boy is one crazy character. He may not have been a big time gangster, but he feared no man.

Joe Cabot – Reservoir Dogs

The leader. Not to mention it’s Laurence Tierney. Guy was born gangster.

Cody Jarrett – White Heat

Going back to 1949, Jame Cagney played this role to a tee. If you haven’t seen White Heat, it’s definitely worth it. Cagney plays a guy who breaks out of prison to lead his old gang in a chemical plant payroll heist.

Tony Montana – Scarface

Anyone who uses the F-word that often has to be on this list.  Did you know that Scarface had something like 400 uses of that word?  It’s insane.  Al Pacino must be loving reading this article because he’s appeared multiple times.  But honestly he deserves it.  When you’re mentioned in that many rap songs you know you’ve reached amazing gangster status.  It doesn’t get more gangster than Tony Montana.

Sonny Corleone – The Godfather

He may have died but you just don’t get much cooler than Sonny. Devoted to his family and will take down anyone who even remotely threatens them. Highly tempered but great with the ladies.

Han – Enter the Dragon

Han built up quite a little gang there in his private island. If it weren’t for Bruce Lee coming in and busting him through, he’d probably still be running his dope operation overseas.

Junior – Kiss of Death

He may have had asthma but he made a guy strip on stage and bench pressed a chick 40 times.

The Joker – Any Batman

Certainly a different kind of gangster and perhaps the scariest, the Joker isn’t on any side. He just is.  And he’s amazing.