10 best Gangsters of modern cinema & television– Pt 1

10 best Gangsters of modern cinema & television– Pt 1

Gangsters have had almost as much influence on TV and movie culture as they have on American commerce and law enforcement. Here’s “The Boss”‘s top ten movie/TV Gangsters of of the past forty years.

10. Bill the Butcher “Gangs of New York”

“That’s a wound!”

Though the script was a touch flawed, there has never been a bolder vision of down and dirty mid-nineteenth century New York gangland as Scorcese’s Gangs of New York. And there’s never been a more over-the-top bombastic lord of the slums than Daniel Day Lewis’ Bill the Butcher. Equally charismatic as he was ruthlessly psychotic, Lewis’ butcher was larger than life as only the Boss of the Five Points, the most dangerous neighborhood in America needed to be.


9. Frank Costello “The Departed”

It's all in those crazy eyes.

A very different Gangster than his real-life namesake (who retired from his post as acting boss of the Luciano family after narrowly dodging a bullet to the head) Jack Nicholson’s aging lunatic Boston crime boss was everything you expect from Nicholson and more (the more being that unmistakeable Bahstin accent.) Whether he was coming out of the back of a pub dripping in blood or telling a prostitute to go for a mountain of cocaine and “don’t stop till you’re numb.” Costello was living proof that not all Gangsters go soft in their latter years.


8. Arnold Rothstein “Boardwalk Empire”

"Can I help you?"

One of the show’s side characters based on a real Gangster, Michael Stuhlbarg portrays a flawless Rothstein as the cool, calm, level-headed and always cautious Rothstein who gained a reputation as one of the greatest gamblers and liquor smugglers in American history. Rothstein made his mark in organized crime by teaching small-minded immigrant thugs how to speak, dress, act, and think like businessmen. Stuhlbarg is making his mark by showing Rothstein in that perfect, diabolically brilliant light.


 7. Christopher Moltisanti “The Sopranos

"What're you lookin' at?"

Definitely one of the more complex and haunted of the Sopranos characters, Christopher was the perfect example of the Generation X gangster: at times aimless, living out Hollywood fantasies, at times ruthlessly ambitions only to be held back by his addictions, sensitivity, and the existential pain of growing up with no father, only “uncles.” His tragic abusive love story and his heartless, cold murder  perfectly portrayed a character who seemed like he was constantly screaming out in pain, only to find his voice muffled to an impotent whisper by “this thing.”

6. Frank Lucas “American Gangster”

"Blue Magic, baby."

Ridley Scott’s magnificent vision of the rise and fall of Frank Lucas showed us the only man in American history to develop a 100% vertically integrated heroin smuggling and distribution racket; something the Italian Mafia never accomplished. Denzel Washington, the finest male black actor working today showed us a Harlem gangster who spoke, dressed and acted like a captain of industry and who knew the essentials of branding, quality control and basic American capitalism as drug dealers since him have never matched. He might also be the only Gangster to rat out all his rivals, come out of prison without two cents to rub together, and still hold up his head in the neighborhood that once made him rich.


The Four Most Important Years in NYC Mob History

(Please read this list while listening to Sinatra’s “It Was Very Good Year”)


The peak of power for East side thug Monk Eastman and Five Points Boss Paul Kelly. It was also the last year for brutal gangster involvement in the local city elections. The 1903 alderman election was so chaotic it sent dozens of Gangsters to Grosvenor Hospital and a few to the morgue. Later in the same year, a gun battle broke out between the same two mobs over control of an East Side card racket called Stuss. The two day-long shootout went down in history as “The Battle of Rivington Street.” The madness couldn’t last forever. Eastman fell out of favor with Tammany and a year later was sent off to Sing Sing for attempted murder. Not long after Kelly was chased out of power by a younger more ruthless set of Sicilian thugs fresh off the boat.

Rough & tumble downtown thug Monk Eastman


The year it all changed: With the enacting of the Volstead act which outlawed the sale, manufacture or transport of intoxicating liquors, Gangsters saw the opportunity to make money in ways they never had before providing the public with something they wanted! It soon became clear that the old, small-time local street gang mentality had to go. Gangsters now had to think, act, speak and dress like businessmen. It was also the previous year that a sharp, slick, uptown wiseguy named Arnold Rothstein made national headlines for “allegedly” fixing the World Series… and got away with it. By 1920 the writing was on the wall: Brawn is helpful, but brains is king.



In the late 1920’s, Sicilian Mobsters were slaughtering each other all over New York City. Joe “The Boss” Masseria declared  independence from the Sicilian Mafia by no longer sending “tribute” back home. Blue-blood intellectual Mafioso Salvatore Maranzano from Castellamare del Golfo came to New York to eliminate Masseria and regain control of New York. After half a decade of violent 1931 saw the end of Masseria, Marazano and the Castellamarese War. The former was gunned down by four unknown assailants at a Coney Island restaurant and the later was stabbed to death by four unknown assailants in his Midtown office. Into the void stepped Charles “Lucky” Luciano who declared himself NOT il capo di tutti cappi (boss of bosses) but as the chairman of a national crime syndicate that enjoyed a 25 year reign of peace and prosperity under his leadership.


The messy end to Masseria's reign


Of course, nothing lasts forever. After ten years of building up Cuba as a gambling haven for well-heeled Americans, the Castro brothers seized control of the country and the tens of millions of dollars the Mob had stashed there. In 1957, Luciano, who had been deported from the U.S. eleven years earlier held a big meeting in Sicily where he established the biggest heroin importation and distribution network in US History. Many members of the mob were opposed to the idea which created a massive rift in the national crime commission. Albert “Mad Hatter” Anastasia was gunned down that October in a Midtown barbershop for his opposition, Frank Costello aka The Prime Minister of the Mob just barely dodged a bullet to his own head, and a Federal bust of a large meeting in Apalachin, NY resulted in the arrest of nearly half of the biggest Mobsters in America. All in one crazy year…

Hitman extraordinaire Albert "Mad Hatter" Anastasia