Nobody would ever want to be face-to-face with the following violent gangsters but these famous actors had an even tougher task ahead of them – they had to become them. Playing a hardened, organised crime leader can prompt quite a few ethical questions – should we rush to the movies to be entertained by their lives or refuse to publicize such horrific crimes any further? This dilemma becomes even tougher when we realize that under the surface, these gangsters can often be quite charismatic and endearing.
Gangsters break the law, commit murder, force extortion rackets onto innocent people, all while turning over a huge profit and audiences can’t get enough. It appears that the more dangerous, repulsive and unforgiving these crime lords become, the harder it is to take our eyes off them.
Francis Ford Coppola’s celebrated classic, The Godfather, was adapted from Mario Puzo’s bestselling series and focuses on the life of Vito Corleone. Although Corleone is a fictional character, the majority of the inspiration was based on real-life mobsters. Marlon Brando didn’t just portray a hardened crime family boss, he also made movie go-ers for decades admire him. But how easy is it for actors who aren’t playing a fictional character? Taking on a role of someone who has destroyed the lives of so many can never be an easy task.
Scenes of shocking brutality are often unwatchable but essential for story-telling and revealing the whole truth. These following actors had to become the anti-hero and completely abandon any human compassion they were holding onto. Here are ten actors who took on the role of the violent gangster and will be remembered for sending a chill down the spines of many.
10. Daniel Day-Lewis as Bill The Butcher – Gangs of New York
Born in 1821, William Poole was more commonly known as Bill the Butcher. A bare-knuckle boxer, he was responsible for the Know Nothing movement which attempted to flush out Irish-American influence in politics. He was the founder and leader of the Bowery Boys, a gang of anti-Irish men based north of the Five Points district in New York City.
In 1854, Bill the Butcher was challenged to a boxing match by his archenemy and Irish immigrant, John Morrissey. Sharing the ring with the Butcher was not a wise decision and Morrissey’s condition was reported in the New York Daily Times after the fight as:
“His eyes were closed and one of them was found to be gouged from one end of the socket, which injury will probably impair his sight for life. His face above and below the eyes is blackened by violent blows given on the bridge of his nose. There is a hole in his cheek, and his lips are chewed up in a frightful manner. He also sustained fearful injuries about his breast, arms, and back, where Poole kicked him with heavy cowhide boots after he helloed enough. So severe are Morrissey’s injuries, that it is very doubtful whether he walks in the street for the next six months”.
When Martin Scorsese made this history into the movie Gangs of New York, he knew he would have to get the casting of Bill the Butcher right. If you need to find an actor who can portray a man capable of such gruesome violence, then look no further than Daniel Day-Lewis. Leonardo Di Caprio co-stars as his opponent, Amsterdam Vallon. He is caught in a horrific moment where he is horribly head-butted and then a scalding knife blade is pressed to his cheek by the Butcher. Lewis is psychotic enough to send a genuine chill down your spine.
9. Sean Penn as Mickey Cohen – Gangster Squad
Los Angeles gangster Mickey Cohen was part of the Jewish Mafia with very strong ties to the Italian American Mafia. His reign of violence was between the 1930s and the 1960s. In 1939, after he was released from prison for being involved in the murder of several men during a bad card game, he set up the Flamingo Hotel in Las Vegas. A few years into the operation, members of another crime family ordered that the hotel manager and mobster, Benny “Bugsy” Siegel, be killed after they believed that he was skimming money. Cohen did not take well to the murder and he entered the Hotel Roosevelt firing rounds from a .45 caliber semi-automatic handgun into the ceiling and demanded that Siegel’s assassins fight him outside.
This and many other violent activities were bought to the attention of state and federal authorities and they began investigating Cohen and his associates. After Cohen’s mansion on Moreno Avenue was attacked by a bomb, he turned his home into a secure fort by installing floodlights, alarm systems and hired close-protection bodyguards. Despite his notorious criminal activity, Cohen was sentenced to just four years in prison for tax evasion in 1951.
Gangster Squad also stars Josh Brolin, Ryan Gosling, Emma Stone and Giovanni Ribisi. Although the movie did not win favourable reviews, Sean Penn dominates the rest of the cast with the twisted and vicious persona of Mickey Cohen. He gives a haunting speech during one scene at a restaurant where he discusses a murder he was involved in. He ruthlessly claims, “That wasn’t murder, that was progress. I am progress.”
8. Stephen Graham as Baby Face Nelson – Public Enemies
It’s not officially a gangster movie until British actor Stephen Graham has a part. Starring alongside Johnny Depp in Public Enemies, Graham plays Baby Face Nelson, real name Lester Gillis, who was an American bank robber during the 1930s. He was known as “Baby Face” due to his youthful appearance and lack of height.
John Dillinger, played by Johnny Depp, was a notorious bank robber who had broke into over twenty vaults. When he was imprisoned, it was Baby Face Nelson who broke him out and the two went into partnership. Shortly after this time, their new gang became the number one public enemy. During bank robberies, Baby Face and his gang would often shoot like mad-men at anyone who could be seen as getting in their way. He killed many people, including the most number of FBI agents which was three in total.
Nelson died very differently in real-life than in Public Enemies but he certainly did go out with a bang. In 1934, he was surrounded by FBI agents who opened fire. He was shot in the stomach, the bullet slicing through his liver and pancreas before exiting out of his back. Despite his fatal injuries, he walked towards the agents firing his own shots back at them. Before he managed to escape in a getaway car, he had been shot a total of seventeen times. He told those with him “I’m done for” and instructed them to drive to a nearby safe house where he died in bed beside his wife.
7. Warren Beatty as Clyde Barrow – Bonnie and Clyde
Clyde Barrow is probably one of the most infamous and murderous gangsters of all time. So who better to play him in Bonnie and Clyde than award-wining actor, Warren Beatty. Clyde was born into a poor family in Ellis County, Texas. During his childhood, he slept with his family underneath a wagon until they eventually saved enough money to buy a tent. He turned to crime quite early on in life and would often steal cars and rob stores. After many arrests, he was eventually sent to Eastham Prison farm in 1930. During this stretch in prison, he killed another inmate by crushing his skull with a lead pipe. Clyde told the prison guards he had been repeatedly sexually assaulted by the inmate.
In 1932, he left prison and turned to crime again but this time he was even more bitter after his treatment behind bars. In the book, Running With Bonnie and Clyde by John Neal Philips, it was said that his sister, Maria, claimed, “Something awful sure must have happened to him in prison, because he wasn’t the same person when he got out.” He robbed grocery stores and gas stations with a M1918 Browning Automatic Rifle. In 1930, he met Bonnie Parker after visiting a friend and the two were completely smitten with each other.
Bonnie and Clyde was released in 1967 starring Beatty and Faye Dunaway as Bonnie. The pair begin to grow their gang of gun-toting, chain-smoking robbers on the run and eventually their exploits turn even more violent. On screen, Beatty knows exactly what he is doing and how to portray Clyde in the film. He’s compassionate when it comes to his girl but the rest of the world, he just wants to watch burn. Every murder he commits is just another two fingers up towards the prison system he hates so much. Bonnie and Clyde finally met their fate in 1934, they were ambushed by four Texas officers on a rural road and shot to death in the front of their car.
6. Tom Hardy as The Kray Twins – Legend
Ronald “Ronnie” and Reginald “Reggie” were known as the infamous Kray twins who were identical and born just ten minutes apart. After their earlier criminal records ended their boxing careers, they turned to organised crime instead. The British gangsters indulged in arson, protection rackets, assaults, and even murders around the East End area of London throughout the 1950s and 1960s. They were also West End nightclub owners who gained celebrity status after mixing with well-known entertainers such as Frank Sinatra and Judy Garland.
The Krays were both handed life sentences in 1969 for the murder of Jack “The Hat” McVitie, who they had knifed to death. Ronnie was also convicted at the same hearing for the murder of George Cornell who had called him a “fat poof”, so he shot him between the eyes. In an interview with The Independent in 1995, Reggie said, “I have got no regrets, my brother didn’t have any either. I would not change anything. You can’t just select parts of your life and alter them. I know Ronnie would not have wanted to change anything as well”. Ronnie died in Broadmoor Hospital in 1995 and five years later, Reggie passed away with cancer.
Tom Hardy took on the role as both of the identical twins in Legend. Born in Hammersmith, London, he documents the rise and the fall of the twosome who terrorized the streets of the capital city. Sleek, humorous and yet deadly violent, Hardy manages to portray the twins perfectly showing the world how deeply unhinged they both were.
5. Vincent Cassel as Jacques Mesrine – Mesrine Part 1 & 2
Jacques Mesrine was known as the Man of Many Faces. The Parisian-born criminal was able to remain under disguise during the time he was a wanted man for murder, kidnapping and bank robbing around the world. A pathological psychopath, he broke free of every jail and bragged that he was responsible for more than forty murders. He was hailed by the general public as a Robin Hood character despite his monstrous crimes.
Vincent Cassel took on the role as Mesrine for two movies about his life, Mesrine Part 1: Killer Instinct and Mesrine Part 2: Public Enemy #1. It documents his lifestyle, crimes and his death. His last crime was when he attempted to kidnap a judge who had previously sentenced him to 20 years in prison. Mesrine demanded that all top security prisons in France were to be closed or he would begin to assassinate magistrates in the court. He evaded capture by running down the stairs towards police officers shouting, “Quick! Mesrine’s up there!”.
This was the final straw and French President Giscard d’Estaing declared, “We really have to finish this Mesrine off”. Days later, he was shot dead behind the wheel of his car by officers.
4. Al Pacino as Benjamin “Lefty” Ruggiero – Donnie Brasco
Donnie Brasco is a movie based on the true story of an FBI undercover agent, played by Johnny Depp, who went after the Bonanno crime family in the 1970s. Brasco managed to befriend Benjamin “Lefty” Ruggiero, played by Al Pacino, and the two became such good friends he was even invited to be the best man at his 1977 wedding. Lefty taught Brasco all about being a wiseguy. He explained, “Donnie, as a wiseguy you can lie, you can cheat, you can steal, you can kill people – legitimately. You can do any goddamn thing you want and nobody can say anything about it. Who wouldn’t want to be a wiseguy?”.
In 1979, there was a power struggle within the crime family. Three rebel capos – high-ranking Mafia members – were brought to a meeting where they were murdered, beginning an outbreak of gang wars within the families. In 1981, the FBI began to fear that the turf war would end up killing those they needed to convict. They revealed Donnie Brasco’s true identity to the mobsters and called an end to the operation.
Outraged an informant had made their way into the family, the Bonnano family put out a bounty on the head of Lefty as they held him responsible for letting Brasco in. FBI agents arrested Lefty on his way to a meeting with the family and he was place under protective custody. It was believed that there was a set-up to have him killed at that same meeting.
After his arrest, Lefty was convinced that Brasco was his associate and that he was being told he was an undercover agent to make him confess. He still believed this as fact until Brasco, under his real name Joseph Pistone, gave evidence in court of his investigation. Lefty was sentenced to twenty years in prison; he served eleven and died aged 68-years-old of lung cancer.
3. Denzel Washington as Frank Lucas – American Gangster
During the late 1960s and early 1970s, Frank Lucas was one of the most notorious heroin kingpins in Harlem, Manhattan and a truly feared gangster. He pioneered a new effort to triple his money, by cutting out the middleman and buying his drugs direct from SouthEast Asia. Lucas claimed the incident that turned him to a life of crime occurred when his 12-year-old cousin was murdered by the Ku Klux Klan for looking at a white woman.
As seen in the movie American Gangster, Lucas smuggles the shipments of heroin into the country by using the coffins of dead soldiers. In 2000, he told New York magazine, “Who the hell is gonna look in a dead soldier’s coffin? We had him make up 28 copies of the government coffins – except we fixed them up with false bottoms, big enough to load up with six, maybe eight kilos. It had to be snug. You couldn’t have s**t sliding around”.
It would be quite the hard task to imagine any other actor in this role other than Denzel Washington as Frank Lucas. Uncaring of what devastation class-A narcotics can do a community, he acknowledges everything as solely business. It is a hard task to be likable as a character who flooded the streets with heroin, killed hundreds of people and destroyed communities – but Washington is an actor who never shies from a real challenge.
2. Ray Liotta as Henry Hill – Goodfellas
Goodfellas is one of the most celebrated gangster movies of all time, based on the true crime book Wiseguy: Life in a Mafia Family by Nicholas Pileggi. The book documents the life of Henry Hill, played by Ray Liotta, who grew up with eight siblings in the rundown East New York section of Brooklyn. Mobsters would meet each other on his street and at just eleven years old, he began to run errands for them. It was through his early job that he met Lucchese family associate, James “Jimmy the Gent” Burke (Robert De Niro). Since 1956, he began to profit from crime.
Burke owned a bar called Robert’s Lounge and it was here they had a welcome home party for made man William “Billy Batts” Bentvena after he had spent sixteen years inside. Burke and Billy Batts were not on good terms after Burke took over a loan shark business belonging to Batts during his stretch inside. Instead of returning the business to Batts, Burke had decided to kill him. Exactly as it plays out in the movie, Batts asks Tommy DeSimone, played by Joe Pesci, if he still shines shoes. DeSimone told Hill and Burke, “I’m gonna kill that f***”.
DeSimone shot Batts whilst Burke held him down, then the three of them took the body to dispose of it. Hill recalls driving and hearing banging from the trunk and he realized Batts was still alive. He remembers, “We’re on our way to bury him and he wasn’t even dead”. DeSimone finished him off, properly this time, with a shovel as he lay in the trunk.
Henry Hill praised Ray Liotta for his performance in Goodfellas. He captures Hill’s violent streak when he beats a boy with the handle of his gun until his nose breaks after he touched his girlfriend and eventual wife, Karen. Although Liotta didn’t meet Hill before the filming, he told press at the Tribeca Film Festival this year, “(Martin Scorsese) didn’t want me to talk to him before (the movie). So after the movie, I got a call to meet him at a bowling alley in the valley in California, with his brother. So I go to the bowling alley and there’s Henry – I knew him from pictures. And the first thing he says to me was, ‘Thanks for making me not look like a scumbag'”. Hill passed away in 2012 aged 69-years-old after a long battle with illness.
1. Robert De Niro as Al Capone – The Untouchables
In The Untouchables, Robert De Niro nails the role of Al Capone. Known also as “Scarface”, the infamous American gangster founded and ran the Chicago Outfit for several years during the Prohibition era. Capone was well-known for violence and he was responsible for the St.Valentine’s Day Massacre in 1929. Capone sent his men into a rival’s hangout disguised as uniformed police officers. They lined the rival mobsters up against the wall and fired Tommy guns at all seven men who were left massacred on the floor.
In November 1931, Capone was sentenced to eleven years in federal prison for evading taxes. When incarcerated at Atlanta U.S Penitentiary aged 33-years-old, he was diagnosed with syphilis and gonorrhoea. He also began to suffer from severe withdrawal symptoms from cocaine, which had destroyed his septum over the years. He left prison in 1939; eight years later he suffered from a fatal cardiac arrest. He died the next day at home surrounded by family.
The Untouchables captures everything the Prohibition era will be remembered for – fast cars, gorgeous women and a lot of guns. Also starring Kevin Costner, Sean Connery and Andy Garcia, it was De Niro’s lead role that brought the entire movie together. His ability to fly into uncontrollable rage and the stare which can kill a man on the spot is exactly how we want our evil mob bosses on screen.