The Top 10 Gangster Movie Roles of All Time

“As far back as I can remember I always wanted to be a gangster…”  Every gangster movie fan will recall that quote from the film Goodfellas delivered ominously by Ray Liotta.  American society’s  fascination with violence and power did not escape me as a child, and as far back as I can remember, I was always a fan of the Gangster movie genre.  I watched gangster movies so much as a kid, I felt like some of these characters actually resided with me in my living room, or could have been members of my family-La Colesa Nostra has a good ring to it don’t you think?  So I thought it was time to compile a top ten list of my favorite gangsters in cinema.  (Number one being my favorite, in descending order).  So ladies and gentlemen, I hope you brought your bullet proof flash drives with you and remember not to sit with your backs facing your web portal, because this could get ugly…

10.  Chazz Palminteri as Sonny LoSpecchio in A Bronx Tale:  Everything about Sonny is cool, from his suits, to the way he talks with his fingers, to the way he drives his car in reverse around the block.  I have to admit, I took my vehicle for a spin in reverse around a block or two after watching this movie over and over again.  Fortunately the police didn’t catch me acting out my gangster fantasies of being Sonny the mob boss in my 1994 Ford Escort Sport.  Those were the days, when I could follow Sonny’s advice about dumping a girl on the spot if she was too selfish to reach over and unlock my door from the inside after I extended the courtesy of opening and shutting her car door for her.  Now that philosophy is obsolete because of electric and remote access locks.  But one of Sonny’s maxims, “Sometimes hurting somebody ain’t the answer”  still rings true today, as he schools Calogero AKA “C” during his frustration over an attempt to collect $20 he lent to a friend of his.  Sonny tells him, “He’s outta your life for $20, you got off cheap, forget it,” after convincing C that violence is not necessary to solve such a small problem.  Who says gangsters can’t be diplomatic?

9.  Gregory Hines as Goldy in A Rage in Harlem:  The virtuoso of Tap dance scores big time in this mad rush for gold gangster story in which  Mississippi and New York mobsters clash over loot and booty.  One of the best chase scenes ever filmed features Gregory Hines’ Goldy dashing up flights of stairs, flying from roof top to roof top, and in and out of get-away-cars.  Goldy’s footwork is as fanciful as the real life Hines’ dance choreography and his timing with his gun as sharp as the moves he flashed on Broadway.  Any good crime and suspense drama is always enhanced by comic relief, and Goldy wisecracks with the best of them!  Never once is he fooled by a pretty smile or intimidated by an opponent, be it crook or copper.  The gold is what is eminent, hence the appropriate moniker – Goldy.  From his first appearance on screen, groovily strolling out of a ballroom where later Screamin’ Jay Hawkins will perform at the Annual Undertaker’s Ball, momentarily pausing to greet a pretty girl on the sidewalk, and seconds later warding off a mob boss, all within a couple of strides, Goldy makes a memorable impression.

8.  Joe Pesci as Tommy DeVito in Goodfellas: The character of Tommy is more like the Terminator than a button; a true maniac that somehow in his madness conjures up wit and charisma that makes you laugh seconds before or after he’s just totally annihilated somebody for no reason at all.  But I’m not going to lie.  If I had to go to war and I was in the trenches on a battlefield, there’s no doubt I would be calling Tommy to come to my aid.  This guy is a machine, a time bomb just waiting to explode.  Don’t ever remind him he used to shine shoes before he wore silk suits, forget to serve him a drink at a game of cards, or embarrass him in public.  Because if you do, believe me you’re asking for trouble…and lots of it!

7.  Tupac Shakur as Roland Bishop in Juice:  It’s been 19 years since Juice was released in theaters and I still haven’t forgiven Bishop for killing Raheem.  I mean everything was going as planned: they got in the store, they successfully held it up, they were on their way to proving they belonged in the same league as Radames, and then BANG!  Bishop becomes the neighborhood’s worst nightmare.  Q couldn’t even finish his set at the DJ contest with a clear conscious, and he had been waiting for that moment his whole life…Queen Latifah was hosting man!  But I thought Bishop was the definition of cool when I was a teenager: The Gumby box fade, the flowing hoody, the baggy jeans and boots, and the machine gun necklace charm.  Bishop turned me on to James Cagney movies like White Heat (“Made it ma, top of the world!”) and made being an outlaw look like a never ending adrenaline rush.  Tupac proved to be the quintessential artist, having certainly acquired his acting chops at the Baltimore School for the Arts as a teen.  As Bishop, he sums up his significance within his crew and in Hollywood with the now infamous line, “I’m the one ya’ll need to be worried about, partner!”  Classic!

6.  Calvin Lockhart as Silky Slim and Biggie Smalls in Uptown Saturday Night and Let’s Do it Again:  Both of these Sidney Poitier directed films starring him and Bill Cosby were second to none in my household growing up as a kid.  Calvin Lockhart’s portrayals are consistently as gangster as it gets and it’s difficult to choose one role over the other in each of the films, so I had to pair his characters together in the number 6 slot.  When Silky Slim holds up Madame Zenobia’s establishment, he delivers the smoothest line I’ve ever heard in my life.  With a machine gun clutched in his hands and mask over his face, he thanks the crowd for their cooperation by saying, “Never before have so few owed so much to so many.”  Whew!  It get’s even better in Let’s Do it Again when he and John Amos who, cast as Kansas City Mack, gets an honorable mention in this top ten list, go at each other’s throats over gambling territory in New Orleans, LA.  Lockhart’s Biggie Smalls (Yes that’s where The Notorious B.I.G. got his alias) is cooler than cool, with a gritty baritone voice best described as unearthly, and wardrobe including leather jackets, platforms and berets.  He looks like he could have just finished a set with Curtis Mayfield, who provides the masterful score for Let’s Do it Again, as he collects and pays off.

5.  Robert De Niro as Vito Corleone and Al Pacino as Michael Corleone in The Godfather Part II:  Another tandem this time fills in the 5th spot on this list, appropriately so, as there is no way for me to choose between these two phenomenal actors portraying two memorable roles.  The Godfather Part II and it’s two main protagonists simply are a cut above most gangster films because of the way the past tale of Vito Corleone is intricately woven into the present story of Michael Corleone.  Vito’s rise to power is chronicled by his emergence as a man of the common people, standing up to tyranny and economic exploitation.  Michael is left to struggle with his own demons in his attempt to establish his family’s business as legitimate.  From Vito insisting a neighbor’s rent be reduced by a greedy landlord, to Michael’s chess match with hypocritical government representatives who rendezvous in fancy hotels with mistresses, the Corleone men aim to find their place in world full of deceit, tricks and lies.  And they do it often by making offers others seldom can refuse.

4.  James Cagney as Eddie Bartlett and Humphrey Bogart as George Hally in The Roaring Twenties:  The Depression era takes center stage in this gangster film where Eddie and George, former soldiers in World War I, find themselves interlocked in another war when they return home over bootlegging, prohibition.  If  you’ve  never seen this one, James Cagney’s Eddie Bartlett will dazzle you with right hand hooks that level two brutes with one punch, fits of controlled rage that leave pretend tough guys with their cigars smashed in their faces, and one of the best gangster end scene chase sequences of all time, probably only second to White Heat.  Humphrey Bogart’s George Hally is no slouch either, with an itchy trigger finger and dialing finger, never hesitating to put in his own work or telephone someone else to carry out his orders.  The two characters combine to produce something really special in this timeless tale of early 2oth century America.

3.  Denzel Washington as Frank Lucas in American Gangster:  I literally watched this movie every single time it was broadcast on HBO when it was first released on cable, for like three weeks, or so it seemed.  Wow!  I understand this was a biopic and horrible events occurred in the real life account of Frank Lucas, but didn’t Denzel make you want to fill out a job application for his organization in this one?  Maybe it’s just me, but I definitely wanted to go along on the ride to meet beautiful Puerto Rican beauty pageant winners, sit ringside at heavy weight championship bouts, fly to Vietnam and tell kingpins and warlords, uninvited, that I didn’t need anyone’s permission to run my own business in the states, and hold serve in a game reserved for Anglo Saxons and Italians.  This character was some sort of three-part Molotov cocktail made up of politics, entrepreneurship, and racketeering.  And he knew how to properly maintain carpet, as he emphatically reminded us when his was stained during a party, to use club soda and blot…never rub!

2.  Samuel L. Jackson as Jules Winnfield in Pulp Fiction:  “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 attempt to poison and destroy my brothers.  And you will know my name is the Lord when I lay my vengeance upon thee.”  -Jules Winnfield.  Um…Mr. scary  hit man with the curly afro who just ate my Big Kahuna burger and drank my Sprite, I know I offended your boss and that I am guilty.  But could you please just have mercy on me and kill me without reciting that Bible scripture first, because, I’ve never heard such a frightening thing!  I think that’s how I would have responded to Jules Winnfield’s soliloquy if I was Brett, the victim, right after I lost control of my bodily fluids, and in between my tears and snotty, running nose.  I honestly don’t know of a scarier hit man in the movies than Jules, who is more like a wandering philosopher.  One minute he has me cracking up with laughter, the next minute contemplating miracles, and the next, double checking to make sure my door is locked.  And no gangster has ever had better hair, period.

And the number 1 gangster movie role of all time is (drum roll please)…James Caan as Santino “Sonny” Corleone in The Godfather:  I believe, way down in my heart, that as a child, I was immediately traumatized when I saw Sonny mowed down like wheat in a field at that tollbooth.  At that young tender age, I knew nothing about stunts, special effects, blank ammunition, and fake blood.  All I knew was that my hero, who saved Rocky Balboa’s wife Adrian (Talia Shire) from a physically abusive husband Carlo, by giving him the ass whipping of his life, which included punches to his face, knees to his midsection, biting his knuckles, and hitting him with his own shoe, a garbage can, the lid of the garbage can, and finally kicking him into a spewing fire hydrant, was just shot with a zillion bullets.  I honestly thought it was real the first time I saw it.  What are we going to do about this, I wondered?  Is there anyone we can report this to or can we just take up arms to avenge this?  I was ready to go after those thugs, even if it meant something bad might happen to me, like getting punched or having my toys stolen or something.  But anyone who can hand out a beat down like the one Sonny, my all time favorite cinematic gangster, gives Carlo, and do it without their loose tie strung around the collar of their shirt falling off, has to be the greatest of all time.

© 2011


4 thoughts on “The Top 10 Gangster Movie Roles of All Time

  1. Efficient and concise with the words mi amigo. Might have to let u write up my bio if u keep it up. Lol… Good stuff on the real though. However a little surprised Mr. Tony Montana was off the list…. TWISM.

    • Thanks for the kind words my brotha! It would be a pleasure to write a bio for such a cool cat such as your self, so just let me know when, and I’ll take care of the who, what, where and why! I understand your beef for my leaving out a character who was once asked “And what’s coming to you?” and responded with, “The world chico, and everything in it.” Suffice to say that there are just way too many great gangster characters to sum them all up in a top ten list…but I tried. Thanks for taking the time out to read the article; much obliged!

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