The 20 Greatest On-Screen Gangsters Of All Time

MMD March 20, 2014 0
The 20 Greatest On-Screen Gangsters Of All Time

The gangster has become a phenomenon in pop culture. Every guy in the world has a little place buried deep down in his heart that wishes he was one. It’s not hard to figure out why. Gangsters are blue collar guys, regular Joes just like the rest of us except that live a life of ceaseless action that comes with money, power, respect, women, you name it. These guys didn’t have to go Harvard Law to make their way in the world and they didn’t have a trust fund. All they had was a desire for monetary success and the balls to take what they wanted. Of course, many people have never met a gangster or anything resembling one so they found their favorite gangster in film and on television. It’s probably better that way, don’t ya think? It wouldn’t be good if every financial analyst, carpenter, and cable installer was going around breaking people’s knees. So what we’ve done is put together a list of the greatest gangsters to ever grace the big or small screen and rated them on toughness, coolness, and overall badassery. Here goes the countdown from 20 to 1.


20. Ryan O’Reilly (OZ, Dean Winters)- Oswald State Correctional Facility, better known as OZ was rigidly compartmentalized into a bunch of gangs from the Blacks, to the Hispanics, the Italians, the white Supremacists, and the Muslims all of which had a lot of members. O’Reilly represented the Irish, which was basically him and him alone, but he was such a bad dude they were still a force to be reckoned with. Ryan wasn’t the toughest guy in OZ but he was easily the smartest. Never one to get his hands dirty unless he absolutely had to, O’Reilly was a master manipulator who got others to do his bidding by telling them exactly what they needed to hear. His scheming was right up there with his ability to make power moves and money at the same time. Breaking the prison rule of, “you don’t whack wiseguys”, O’Reilly murdered Nino Schibetta, an imprisoned mob boss by feeding him fine ground up glass in his food so he could take over his prison drug trade. Everybody respected O’Reilly from the Hispanics to the Blacks and he even partnered up with resident psychopath Adebisi on a few occasions. Besides that, O’Reilly beat cancer, seduced the hottie Dr. Nathan, and lasted to the very last episode. O’Reilly was the definition of a survivor.


19. Avon Barksdale (The Wire, Wood Harris)-The Wire is probably the most critically acclaimed show of all time. It focused on the gangsters, cops, teachers, journalists and underprivileged youth of Baltimore. The undisputed king of The Wire gangsters was none other than Avon Barksdale. Avon, who was played by Wood Harris (one of the coolest dudes to ever walk the face of the earth), was an ultra-elusive, twistedly brilliant, oddly sentimental, extremely ruthless, and all around badass gangster who ran the streets of Baltimore along with conservative underboss, Stringer Bell. Avon managed to take over the underworld of Baltimore without a single cop even knowing what he looked like. Obviously, they found out but he still had a pretty good run. Avon didn’t see a jail cell until he was in his 30’s and even in the clink he had major juice. In the end, things didn’t end well but Avon Barksdale remains a legend.


18. Phil Leotardo (The Sopranos, Frank Vincent) – Frank Vincent is a go-to mob character actor. He played Billy Batts in Goodfellas and gave drunken guys and gangster wannabees everywhere a favorite saying in, “go home and get your fuckin’ shine box!” But he is most well known as Phil Leotardo, the fresh out of jail captain and two time boss of the New York crime family on the Sopranos. Phil was a piece of work from the beginning as he was always undermining Tony. His hard-on for Tony only got worse when Tony’s cousin Tony B whacked Phil’s younger brother Billy. It was a constant back and forth between the two until Phil loses it and decides to wipe out the whole New Jersey family. He planned to take out the top three members including Tony and then do business with whoever was left over. Phil manages to get to Bobby Baccala and Silvio Dante but Tony, in his usual fashion, manages to get away. Eventually, even Phil’s closest allies turn on him and give Tony the go ahead to take out Phil. He may have caught one in the head followed by having his head crushed by an SUV but he was a bad dude while it lasted.


17. Sonny LoSpecchio (A Bronx Tale, Chazz Palminteri)- A Bronx Tale was so much more than just a mob movie but it did produce one of the coolest on screen gangsters in Sonny. Sonny was your typical gangster in a lot of ways but we got to see his more human side when he befriended Calogero, a neighborhood kid who witnessed Sonny shoot somebody but didn’t finger him for the cops. He took a legitimate interest in the kid that included keeping him out of the mob life and his head in the books. Sonny dropped some serious wisdom on Calogero when he told him that every man had three great loves in his life and that a woman could only be trusted if she passed the “door test” which said that if she leaned over and unlocked the door of the car after you let her in then she was a keeper but if she didn’t she was selfish and not to be trusted. Sonny also showed his forward thinking by telling Calogero that him dating a black girl was okay because when the lights were off it wouldn’t matter. Sonny even pulled Calogero out of a car full of his friends on their way to firebomb a black neighborhood. Sonny pulling Calogero out of the car saved his life as each and every one of those kids died that night. Unfortunately, Sonny met the same fate as most gangsters when the son of the man who he shot at the beginning of the movie avenged his father’s death by shooting Sonny in the head at point black range. Calogero was there to see it all but in death Sonny was finally able to win the respect of Calogero’s father Lorenzo who had protested Sonny being in his son’s life for years.


16. Walter White (Breaking Bad, Bryan Cranston) – Similar to the Wire, Breaking Bad was one of those television shows that received universal praise from critics and fans alike. The show’s star Walter White started off as a brilliant high school teacher working way below his pay grade because of some bad decisions in his past. A diagnosis of advanced lung cancer makes him realize that he needs to provide for his family once he is gone. A run-in with one of his old students, the at times pretty badass himself Jesse Pinkman, he decides that the best way to build a nest egg for his family is to enter the Meth business. Due to the fact that he is a brilliant chemist he is able to cook up the best Meth the world has ever seen in his “Blue”. Walt crosses the line from desperate man to full blown gangster when he blows up psychotic Mexican drug dealer Tuco’s office and walks out with tens of thousands in cash owed to him. From that point on, even when his cancer went into remission, he didn’t turn back and became the toughest Chemistry teacher ever as he runs people over with cars, shoots some in the head, and partners up with mega-kingpin and founder of the “Los Hermanos” chicken franchise, Gustavo Fring at a salary of 1.5 million dollars a month, whom he later blows up with a bomb he built himself. Walter eventually became his own boss making himself 80 million dollars in the process. He had a knack for getting himself out of any situation whether it was with the law or rival gangsters. He always came out on top until he didn’t. He ended up losing his family, his money, and his life but he took a lot of people down with him. Never has a high school science teacher been so feared.


15. John Gotti (Gotti, Armand Assante) – TV movies, especially ones about the mob, are notoriously shitty. Witness To the Mob, a 1998 movie about famous mob rat Sammy “the Bull” Gravano was a travesty despite Nicholas Turturro doing a decent job. I mean they cast Tom Sizemore as John Gotti for Christ’s sake. With the movie Gotti however, they pulled out all the stops. They not only sprung for Armand Assante as Gotti himself but hired Vincent Pastore, Tony Sirico, Frank Vincent, and the legendary Anthony Quinn as his co-stars. All the aforementioned co-stars did a tremendous job, especially Anthony Quinn as Ainello “Mr. Neil” DellaCrocce, John Gotti’s mafia mentor and underboss of the Gambino crime family but it was Assante who stole the show as the Teflon Don himself. Assante has always played a great tough guy but the FBI must have given him an all access pass to recordings of John Gotti for this role because not only did he look like him but he had the mannerisms down pat. Assante essentially became John Gotti for this part. Gotti loved being a gangster and he couldn’t have cared less about going to jail and Assante was able to capture both of those traits immaculately.


14. Paulie “Walnuts” Gaultieri (The Sopranos, Tony Sirico)- Tony Sirico is another go-to guy for directors looking to cast a gangster and with good reason as before he became a thespian he was associated with the Colombo crime family and had about twenty arrests under his belt. Lucky for us, and the gangster genre as a whole, Tony decided to turn his life around and made appearances in about every gangster movie you can think of. But it was his role as Paulie Walnuts on the iconic HBO television show The Sopranos that made Tony Sirico a household name. First things first, nobody has the look like Paulie. From his slicked backed hair (grey wings included), to his perfectly manicured nails, to his immaculate wardrobe, he had the gangster image down pat. For six seasons he served as Tony Soprano’s most loyal captain albeit an annoying one as Tony couldn’t stand his humming and quirky ways. But Paulie was Tony’s go to guy and never hesitated to whack somebody for him, collect debts for him, or hang a picture of Tony as a general on his wall.


13. Vincent Mancini/Corleone (The Godfather III, Andy Garcia)- Say what you will about the Godfather III, the bottom line is that it was a very good movie, not great, but very good and taking into consideration the fact that it was preceded by possibly the two greatest films ever made that’s saying a lot. And if there was one thing about this movie that was great it was Vincent Mancini (played by Andy Garcia), the child Sonny had out of wedlock with Lucy Mancini (the girl Sonny had pinned against the door in Part 1, remember her?). Sure, Vincent faced a bit of a learning curve as when he first went to his Uncle Michael he seemed to fully inherit his father’s hot temper by biting Joey Zasa’s ear off. That lack of control over his emotions vanished quickly however as soon as his Uncle Michael took him under his wing. Vincent was as smart as a whip with the cunning of his uncle, the compassion and caring nature of his grandfather, and the ability to leave a body in the street a la his father Sonny. Add to this the fact he wore slick clothes, picked up hot chicks effortlessly, and represented the new generation of the Corleone family and you easily have one of the baddest on screen gangsters of all time.


12. Omar Little (The Wire, Michael K. Williams) – There aren’t many characters in any genre that are more interesting than Omar Little. The Wire was full of intriguing people but Omar took the cake. They say every man should have a code and Omar most definitely did. He was the most feared stick-up kid in Baltimore and loved to pull a sawed off shotgun out to rob a drug dealer or two but Omar would likely turn that gun on himself before he ever pulled it on a civilian. And while he stole heroin from one drug kingpin after the next to either sell it back to them or a rival, he had no problem being an openly gay man, often seen with boyfriends, many of whom were his partners in crime. All I will say is this, to be gay and have the biggest drug czars in Baltimore scared of you makes you one tremendously bad motherfucker. Omar’s classic moments include shooting at Avon and Wee-Bey as he pops up with some chees fries for Avon, taking Marlo and his psychotic crew comprised of Chris, Snoop, and Mike head on and jumping out of a third story window while doing so, his famous Western style showdown with feared Muslim hitman Brother Mouzone, and his Brother Mouzone assisted slaying of Stringer Bell.

goodfellas Robert Deniro 1990

11. Jimmy “the Gem” Conway (Goodfellas, Robert Deniro) – Based on real life gangster and associate of mob rat Henry Hill, Jimmy “The Gent” Burke, Jimmy Conway is one of the greatest characters in the history of film. An Irishman, Jimmy stole any and everything in sight and was responsible for the Lufthansa heist, at the time the largest heist in United States history. Jimmy showed Henry Hill the ropes and was a legend in mob circles because remember he’d tip the bartender a hundred just for keeping the ice cubes cold. Besides being an overall badass, some of the things Jimmy did were just hysterical such as choking Maury with a phone cord until his hairpiece fell off. He later killed Maury so he didn’t have to pay him his share of the heist as well as anybody else who was associated with Lufthansa. For proof of what a bad dude Jimmy really was just take notice of the look on his face while he’s kicking the life out of Billy Batts with Tommy. Right after this beating he blamed Batts for denting his shoes.


10. Nicky Santoro (Casino, Joe Pesci)- Based on real life killing machine Tony Spilotro, Nicky Santoro was the first mob boss of Las Vegas in the movie Casino. Originally assigned to Vegas by the Midwest Mafia bosses to protect their favorite gambling Jew Ace Rothstein, who ran the Tangiers casino for them, and keep his eye on the skim, Santoro saw Las Vegas as a much bigger opportunity. It was a wide open town. No family had any real stake in Sin City so he took full advantage by robbing everything that wasn’t nailed down, partaking in loansharking and extortion, and of course by being a restaurateur. Nicky laid the foundation as a tough prick early on by killing a guy twice his size by jamming a pen into his neck about a hundred times after the guy told Ace to shove said pen up his ass. And we can’t forget when he pops Tony Dogs’ eye out with a vice, yeah that’s a great scene, and yes that absolutely happened in real life. Unfortunately for Nicky he starts to develop some vices including bedding every chick in sight and drugs. All the coke starts getting to him and the fact that he started banging Ace’s wife didn’t sit well with the bosses at all. In the end, Nicky just caused too much trouble and he ends up having to watch his brother get beaten to death with a bat by his own crew (of which Frank Vincent was a part of). Right after his brother, Nicky faces the same fate and they are buried in a shallow grave on top of each other stripped down to their underwear. Even worse, they’re buried while they’re still breathing. Talk about a message job.


9. Chalky White (Boardwalk Empire, Michael K. Williams) – From the first episode of Boardwalk Empire it was easy to tell that it was going to be incredible. Between the historical relevance, plot twists, and well developed characters the show is a masterpiece. Even though the show is full of awesome characters, Chalky White, played by Michael K. Williams, manages to stand out. Probably the most badass thing about Chalky is that he navigates the world of white gangsters with ease despite being a Black man in a horribly racist time. We don’t know much about Chalky’s past but he occasionally drops a tidbit that hints at it being pretty crazy (no surprise there). He rules the Black side of town with an iron fist in a silk glove by having a hundred men ready to murder for him at any given moment while still lending a helping hand to those in the community. When he’s not getting Nucky Thompson out of a jam he can be found woodworking in some of the coolest looking tailored clothes you’ve ever seen, driving a sick Packard, or demanding that his beautiful wife make him some Hoppin’ John.  Also, just for good measure, he cuts the head of the KKK’s finger off to determine whether or not he was telling the truth about killing one of his men.


8. Tom Hagen (The Godfather I & II, Robert Duvall)- Tom Hagen defies the belief that a man cannot be half a gangster as he was a pragmatic genius who was equally effective in the courtroom, the boardroom, or a back room Mafia meeting. Tom Hagen was a brilliant attorney, nearly the consigliere of the family, and not to mention the Don of the Corleone family while Michael was away. And yes, Michael did name Hagen the temporary Don despite his German-Irish heritage which in and of itself is incredible. Tom wasn’t the toughest guy but he was ice cold in business matters. Who can forget when Sollozzo kidnapped him and he didn’t break a sweat or when Woltz flipped out on him and he replied by thanking him for a pleasant evening? Tom never let his emotions get in the way of his business, a trait he undoubtedly picked up from Don Vito himself. There also wasn’t much Tom didn’t know. He always stayed informed and his mind was razor sharp. He may not have been a war time consigliere but he could have been the Don of any family.


7. Al Capone (Boardwalk Empire, Stephen Graham)- I obviously wasn’t around in the 1920’s so I didn’t get to live through Al Capone’s heyday but I have read a lot of books on the man, seen a lot of documentaries, and seen him portrayed in movies. In my head I’ve come up with an image of what Al Capone should act, talk, and walk like and that is exactly the Al Capone I see on Boardwalk Empire. And I have to give a massive amount of credit to Stephen Graham for bringing this character to life especially with a British accent which shocked the hell out of me the first time I heard it, a true testament to his stellar performance. At the beginning of Boardwalk Empire we see Capone as a young Brooklyn tough brought over to Chicago by Johnny Torrio to serve as muscle. He runs a cathouse and throws the occasional beating. It’s only a matter of time before Capone gets more responsibility and climbs up the ranks of the Outfit until he is Torrio’s underboss. Capone is a born leader and after Torrio takes a trip to Italy that changes his outlook on life, Al Capone, for all intents and purposes, becomes the boss of “the Outfit”. Capone is ruthless and business savvy making money hand over fist with liquor and prostitution but he does have a soft side as he often caters to his deaf son and beats one of Dean O’Banion’s men, Joe Miller, to a bloody pulp with his bare hands for calling his head bagman Jake Guzik fat and smelly. The beating doesn’t show his soft side but the reason does. Hell, he even threw a wad of money in the air to pay for Joe Miller’s funeral. Capone is a gangster’s gangster.


6. Arnold Rothstein (Boardwalk Empire, Michael Stuhlbarg) – Okay, so here’s the skinny on the real Arnold Rothstein as we don’t get a backstory on Boardwalk Empire. Arnold Rothstein was a New York City gangster who literally built up a ridiculous fortune a dollar at a time starting when he was just a kid. He gambled, came up with ingenious schemes, but overall kept a veil of legitimacy over his base criminality. He was the toast of New York City and he had a couple of nicknames that most men would give their left leg for such as “the brain” and “the big bankroll”. He was instrumental, through his mentoring of several young gangsters, in the formation of the modern Italian Mafia and he is most famous as being the man who fixed the 1919 World Series, which was never totally proven, but I mean c’mon, he probably did it.  The casting crew at Boardwalk Empire absolutely killed it when they picked Michael Stuhlbarg. He is the perfect Arnold Rothstein. Besides being historically accurate, Rothstein is overall just a bad dude. He doesn’t exactly fit the role of a typical gangster like an Al Capone or a John Gotti and that’s what makes him interesting. He’s sophisticated, well spoken, ruthless, and essentially devoid of all human emotion, an odd combination of characteristics. Rothstein demands the respect of such ruthless and ambitious gangsters such as Lucky Luciano and Joe Masseria. As far as bosses go Arnold Rothstein is as big as you can get.


5. Nucky Thompson (Boardwalk Empire, Steve Buscemi) – When Boardwalk Empire first aired Nucky was the corrupt treasurer of Atlantic City. He had his hands deep into politics but also ran the whole town and made a boatload of money doing it. As the treasurer of Atlantic City, Nucky had some major juice, so much juice in fact that he helped get Warren G. Harding elected President of the United States. Nucky ended up catching a charge related to his political corruption. He beat the case but it effectively ended his career as a politician. For your average guy, that might have been a problem. Nucky just took it as an opportunity to be an even better gangster by becoming one of the biggest bootleggers in the United States. Some of the people Nucky bested were his former protégé Jimmy Darmody, his former mentor the Commodore, Arnold Rothstein, Gyp Rossetti, and Joe Masseria. Nucky has a knack for fighting stronger opponents and still coming out on top. He’s a survivor, a winner, and the king of Atlantic City. Not many on screen gangsters have proven to be more elusive and ingenious and despite being nothing more than a gangster now Nucky still has some of the most powerful men in the United States in his pocket.


4. Anthony Soprano (The Sopranos, James Gandolfini)-The Sopranos is easily one of the most realistic depictions of mob life ever to be seen on screen. Want to see the apex of success for a mob boss today? Tony Soprano is it. Though not the official boss for a while, due to an ailing Jackie Aprile who was serving as acting boss and then Tony’s Uncle Junior being placed in the big chair by Tony himself in order to keep the heat off of him, Tony was calling the shots from episode one. Tony had a few hiccups in his life like getting shot by his Uncle Junior, the occasional crazy goomada, and passing out due to panic attacks but I believe one of the strongest undertones of the show is what a lucky bastard he really was. I mean, he was constantly flush with cash, had a hot MILF of a wife in Carmella, a string of gorgeous mistresses, two healthy kids, a gorgeous home, and for the most part a loyal crew. He owned the Bada Bing with Sil and never saw any real legal troubles. I think the viewers saw Tony incarcerated for a total of about three hours during the whole duration of the series. And on top of all that, Tony, despite being the boss of the bastard stepchild of the New York City Mafia was well respected across the board and made the DiMeo family of North Jersey a force to be reckoned with.(R.I.P James Gandolfini)

The Godfather movie image Al Pacino

3. Michael Corleone (The Godfather I, II, & III, Al Pacino) – Michael Corleone is a complex character to say the least. He started off as a college kid turned war hero. Unlike his brothers Sonny and Fredo he wanted nothing to do with his father Vito’s business despite easily being the most capable of the three. He seemed destined for greatness in the legitimate world. It wasn’t until there was an attempt on his father’s life that we saw the other side of Michael. To make sure his father was out of harm’s way he murdered Sollozzo and McCluskey, a police captain, in cold blood. He fled to Sicily while everybody else cleaned up the mess in the United States and this is where we see Michael embrace his new identity as a gangster, namely when he threatens Apollonia’s father so that he allows him to court her. When he is finally able to return home it is assumed that he is the new head of the Corleone family. The thing about Michael is that one would assume that because of his loyalty to his family and the Sicilian blood running through his veins he would do what he had to do to keep the family afloat but not have his whole heart in it. While Michael seems somewhat conflicted it doesn’t stop him from becoming horribly ruthless, which we can truly see in the murder of his own brother Fredo. The question is, is Michael going too far or is he simply carrying on a tradition as a matter of duty? In the end, he becomes one of the richest men in the United States and the undisputed boss of bosses. Unfortunately, he loses a daughter in the process and dies alone.

The Godfather movie image Robert De Niro

2. Young Vito Corleone (The Godfather II, Robert Deniro) – Young Vito Corleone was the definition of a man’s man. Just look at this kid’s life. His brother is killed because he tried to avenge the death of his father. The local Don in Corleone, Sicily, Don Ciccio, then has it out for Vito despite him being a young child. It was a Sicilian belief that if a man’s father is killed his sons must be murdered as well because they will seek vengeance when they are older and stronger. In a fit of desperation Vito’s mother goes to the Don with Vito and pleads for her youngest son’s life claiming he could never hurt anybody because he was dimwitted (not a great character assessment there) to which the Don coldly replied that Vito must die because he will grow strong and seek vengeance on him (a more accurate assessment). Vito’s mother held the Don at knifepoint and told Vito to run before the Don’s bodyguards sent her flying through the air with a shotgun blast. Vito witnessed it all. He was hidden by some family friends who sent him alone on a ship to America. When he arrived at Ellis Island, with the stroke of a pen, he went from Vito Andolini to Vito Corleone. He was all alone. By the time we see Vito again he is a grown man, married with a child. Things were tough for Vito. He loses his job working at a grocer so the local Mafia chief Don Fanucci can get his nephew a job. The owner of the grocery offers Vito food for his family and Vito turns him down but still hugs him and thanks him for how he had looked out for him. Vito was accidentally led into his first criminal act when Clemenza returned a favor to Vito by “giving” him a rug. With no other options and a family to feed Vito begins stealing goods with Clemenza and Tessio. When Fanucci demands a tribute from their profits, Vito agrees but has other plans. He impresses Don Fanucci by offering him a smaller amount of money than what was demanded claiming he would get him the rest. Just minutes later he shoots Don Fanucci in the face and takes the money back. Vito Corleone, the Godfather, was officially born. My personal favorite part of the movie is when Vito returns to Sicily to check on his olive oil interests and goes to get his blessings to begin work from Don Ciccio who had killed his family. He leans in to speak to him and proceeds to jam a knife into his stomach, drag it up to his heart and snuff him in the head with a look of disgust. Avenging the death of your family about 30 years after it happened is the action of a true Don.


1. Vito Corleone (The Godfather I, Marlon Brando) – Vito Corleone is the quintessential Don. Who he is actually based on has been debated for years. Some say Carlo Gambino, some say Joe Bonanno but nobody really knows. Either way he is the ultimate on screen gangster, the well from which all other writers have drawn when writing similar characters. Vito has characteristics so many other gangsters don’t. He is kind, caring, and generous. He loves children and sees the innocence in them. None of this kindness should be mistaken for weakness however. Don Corleone didn’t become the Godfather by being a pushover. Like you can read above he whacked Fanucci and Don Ciccio and I’m sure a string of others.  Even as an older man he survives getting shot multiple times. Vito lived by a code and he opposed the sale of narcotics despite the huge profits to be made. He pulled the strings of the most important politicians and on a less serious note it was absolutely hysterical when he mocked his godson Johnny Fontaine for crying and then slaps him and tells him to act like a man. The Godfather valued family, honor, and integrity and that is what makes him the greatest on screen gangster of all time, that and he’ll make you an offer you can’t refuse.

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