Ah, the gangster film: America's answer to the Spaghetti Western. Whether you have a keen interest in the history of organized crime or are just a plain old garden-variety sociopath, there's no denying the strange allure of these gritty, terse dramas and their violent, unpredictable anti-heroes. With that in mind, Private Island pored through its exhaustive film archive to bring you our list of the top ten gangsters in the history of cinema. Our fedoras are off to these seriously bad dudes.

**WARNING** this article definitely contains movie spoilers. If you somehow love gangster films without having seen any of these movies, maybe take a brief 20-hour movie marathon break before you read any further.

10. Caesar Enrico "Rico" Bandello, Little Caesar

Truly, there is no more iconic gangster in American culture than Edward G. Robinson. If you've ver heard somebody say ANY of the following: "yeah, see?" "you dirty rat!" or "coppers", chances are they're doing an Edward G. Robinson impression (whether they know it or not). And Rico Bandello is perhaps Robinson's best-known role: a two-bit street tough who ascends the ranks of organized crime through sheer reckless brutality, Rico is nonetheless undone when he finds himself unable to carry out the murder of his friend and one-time partner Joe Massara, whom he fears will give him away to police. In a frankly touching display of humanity, Bandello actually saves Joe's life, thus sealing both his own fate and his legendary status as one of the best movie gangsters of all time.

9. Tommy DeVito, Goodfellas

Joe Pesci is another name that's simply synonymous with gangster culture. Though he's played too many high-profile gangster-type roles to mention--his role as Nicky Santoro in Casino certainly springs to mind--we just have to give it to him for his chilling portrayal of Tommy DeVito in Goodfellas. He cements his status as a force of nature akin to a tornado--that is to say, violent and unpredictable--in the all-too-famous bar scene when Ray Liotta's innocent compliment ("you're a funny guy") provokes an unexpected torrent of anger and intimidation. I'm willing to bet that audiences worldwide breathed a heavy sigh of relief when Tommy finally gets whacked, thus putting an end to his reign of terror.

8. Rory Breaker, Lock, Stock & Two Smoking Barrels

 

Though a relative unknown in the gangster movie scene, Vas Blackwood scores some serious points for his riveting portrayal of Rory Breaker, criminal psychopath and all-around cool customer, in the cult classic Lock, Stock & Two Smoking Barrels. Breaker, despite his somewhat unassuming exterior, nonetheless inspires pure, unadulterated fear in anyone foolish enough to cross his path. In perhaps the best example of this fact, Rory exacts chilling, calculated revenge on a poor fellow whose only crime was to switch the channel of a bar TV off of the football match he was watching. Breaker reacts as follows: 1. calmly, he picks up the bar's fire extinguisher and places it outside the entrance, 2. returning to the bar, he orders a tall glass of the tavern's strongest liquor, 3. he switches the channel back to the game, 4. when the man who switched the channel stands up to protest, he spits a mouthful of the high-proof liquor all over his face and chest, and proceeds to light him on fire. If that alone doesn't earn him a spot on our top ten list, I can't imagine what would.

7. Mr. Blonde, Reservoir Dogs

Anyone who's even vaguely familiar with the works of Quentin Tarantino probably knows that he's a master at crafting complex characters that are simultaneously compelling and terrifying. But he outdid himself in this respect when he cast Michael Madsen as the bone-rattling Mr. Blonde, a psychopath whose propensity for unbelievable cruelty is matched by his unnerving sangfroid. This is probably best captured by the unforgettable scene in which he slowly tortures a captured police officer with an old-fashioned straight razor and prepares to light him on fire, all while dancing eerily to Stuck in the Middle With You by Steeler's Wheel. I think it's safe to assume that that particular song is now thoroughly ruined for anyone who's seen the movie and possesses even the merest shred of empathy.

6. Frank Costello, The Departed

I must admit, having grown up in the Boston area, I have a specific fondness for The Departed. Especially since, being of mixed Italian/Irish ancestry, it's nice to see the other half of my lineage get its fair share of credit for being bloodthirsty criminals. That aside, you don't need my personal background to see the appeal of Jack Nicholson playing a fictionalized Whitey Bulgur in a film by Martin Scorcese. That's like winning the Triple Crown of mob movie greatness.

5. Jef Costelo, Le Samourai

 

Typical close-to-the-fence gangster movie afficionados are probably scratching their receding pompadours in bewilderment at the inclusion of an obscure French film. Well gentlemen, I'd advise you to put down the capicola, wrestle yourself into a clean track suit and drive your black Lincoln Navigator to the nearest place where good movies are sold. Le Samourai is the tale of hitman Jef Costelo (Alain Delon)as he is double-crossed by his erstwhile employers and enters a fight for his life. The film's title is a reference to Costelo's stoic demeanor and scrupulous personal honor code, which predictably leads him to the film's climactic scene. If you need a break from the well-worn gangster classics, I highly suggest you check it out.

4. XXXX (Unnamed Man), Layer Cake

I put him at number 4 because there are a few mob-movie staples I simply couldn't bring myself to unseat, but Daniel Craig in Layer Cake might be my personal favorite movie gangster of all time. In an unusual departure from the classic gangster archetype, the unnamed man is a debonair, upscale businessman-type drug lord who disdains the messy (read: bloody) side of his work and is hoping for nothing more than a peaceful early retirement. But of course, Murphy's Law dictates that this plan won't come off without a hitch, and he finds himself tangled up in a vicious gang war over what was supposed to be his farewell score. In typical cool-customer fashion he survives double-crosses, armies of thugs and even pursuit by an elite assassin... only to find himself shot in the final seconds of the film by a bumbling associate whose girlfriend he had seduced earlier in the movie. The genius of this film is really in its ending--it plays with the established gangster movie conventions, illustrating the violence and unpredictability of mob life by having our protagonist meet his end unexpectedly over a plot point so casual it seems almost inconsequential until viewed with hindsight. Still, I'll admit that I sometimes like to pause the movie about a minute shy of roll credits so that I can imagine him living to the ripe old age of 90 at a tropical island resort somewhere.

3. Jules Winnfield, Pulp Fiction

It's no secret that Samuel L. Jackson deserves a spot somewhere on pretty much any Top-10 list imaginable. I would've even worked him into my list of Film's Top 10 Hottest Princesses... but it seemed like kind of a stretch. Anyway, the good Mr. Jackson definitely gives his most memorable performance as hitman Jules Winnfield in Quentin Tarantino's masterpiece Pulp Fiction. That movie is so chock-full of amazing scenes and choice quotes I can hardly bear to even dissect it, but I think it's safe to say that Jules makes the leap from simple awesomeness to legend status in the film's climactic scene, wherein he reprises his earlier quotation of the Biblical passage Ezekiel 25:17:

"The path of the righteous man is beset on all sides by the inequities of the selfish and the tyranny of evil men. Blessed is he, who in the name of charity and good will, shepherds the weak through the valley of darkness, for he is truly his brother's keeper and the finder of lost children. And I will strike down upon thee with great vengeance and furious anger those who would attempt to poison and destroy my brothers. And you will know my name is the Lord when I lay my vengeance upon thee..."

...this time characterizing himself as neither the righteous man nor the shepherd, but instead as the 'tyranny of evil men'. With this realization, he breaks free of the violent routine that otherwise would surely end in his untimely death--as we see happen with his partner, Vince Vega--and secures for himself a happy ending that's all too uncommon among high-profile gangsters.

2. Tony Montana, Scarface

 

Given its current (and enduring) status as a cult sensation, it's almost hard to believe that Scarface initally met with profoundly mixed reviews after its 1983 release. Though some critics lauded the gritty, unflinching realism of its portrayal of drug-related violence, others found it to be purposeless, gratuitous and downright revolting. Acclaimed author Kurt Vonnegut of Slaughterhouse Five fame is among those reputed to have walked out in disgust during the famous chainsaw scene (and this is someone who fought in WWII.) Personally, I have my own mixed feelings about Scarface--I understand the reasoning behind its appeal, but it lacks the nuance that I feel characterizes a truly outstanding genre film. Nonetheless, if you've been paying even a bit of attention to the list so far, you're probably wise to the trend that a good gangster flick usually boils down to its final climax. And there's really no beating Al Pacino burying his face in a veritable Mount Everest of raw fishscale before picking up a fucking M-16 with grenade launcher and waging an all-out war against basically the whole of Miami's underworld. Whew, I want to listen to Ghostface Killah just thinking about it.

1. Vito Corleone, The Godfather

 

I'm 90% sure that it's actually New York state law that Marlin Brando as Vito Corleone needs to top any list of movie gangsters published within its borders. Some might argue that Michael is actually more worthy of Private Island's highest honor, but Al Pacino already got a nod for playing Tony Montana, and anyway his character is tainted by having the misfortune to survive all the way to The Godfather III, a film generally agreed to have sullied the good name of the trilogy. And anyway, Vito Corleone represents another important gangster archetype: the aging, tired Don whose youthful ambition and thirst for blood have both been thoroughly quenched, and who is now reflecting candidly on his life from the perspective of his twilight years. Despite having reached the zenith of power in his organization, he learns with dismay that his youngest son Michael has followed him into the family business. Vito is remarkable among famous film gangsters for the simple fact that, not only does he live to an old age and die a natural death, he also grapples with the moral and personal fallout of his quest for supremacy. It's for this reason more than any other that he tops the list.

Well there you have it, loyal readers! Be sure to check back for more great articles and Top-10 lists; we're adding more great content every day!

 

This article was published by Private Island Entertainment LLC.

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