12 of The Best On-Screen Portrayals of Real-Life Gangsters

(Written for Filmoria)

Next week sees the release of the hugely anticipated Legend, which stars Tom Hardy as both of the notorious Kray twins. To celebrate the film’s release, we take a look at 12 of the best on-screen portrayals of real-life gangsters in film.

Set to be released on 9th September and directed by Brian Helgeland, Legend tells the story of tells the story of the 1960s twin gangsters, Reggie and Ronnie Kray, two of the most well-known criminals in British history.

From Harvey Keitel‘s Mickey Cohen to Johnny Depp‘s John Dillinger, we’ve had some excellent portrayals of gangsters over the years. Here are 12 of our favourites:

* Bonnie and Clyde – Warren Beatty as Clyde Barrow *

The 1967 film directed by Arthur Penn sees Warren Beatty and Faye Dunaway as the title characters, Clyde Barrow and Bonnie Parker. Bonnie and Clyde gained their reputation as outlaws and robbers, as they traveled across the central United States robbing banks during the Great Depression with their gang. Penn’s film tells the couple’s story incredibly well and although it simplifies their story somewhat, it better shows their side of their crimes, counteracting much of what the press were reporting at the time. Considered a “landmark film”, famous for having “one of the bloodiest death scenes in cinematic history”, the film also prompted other filmmakers to be more open in presenting sex and violence in their own work.

* The Untouchables – Robert De Niro as Al Capone *

Brian De Palma‘s 1987 film, based on Eliot Ness’ autobiographical memoir , follows Ness’ account of the efforts his ‘Untouchables’ team took to bring the famous Al Capone to justice during the Prohibition. The film stars Kevin Costner as Ness, Robert De Niro as Al Capone, and Sean Connery as officer Jimmy Malone. Di Niro is perfect is Alphonse Gabriel “Al” Capone, who attained fame during as the co-founder and boss of the Chicago Outfit.

* Bugsy – Harvey Keitel as Mickey Cohen *

The 1991 crime drama Bugsy, directed by Barry Levinson, tells the story of mobster Bugsy Siegel, a Jewish American mobster known as one of the most “infamous and feared gangsters of his day”. The film was written by James Toback from research material by Dean Jennings’ 1967 book We Only Kill Each Other, and starred Warren Beatty as Bugsy and Annette Bening as his lover Virginia Hill.

* Goodfellas – Ray Liotta as Henry Hill *

The first of many Martin Scorsese films in this list, Goodfellas is a 1990 film adaptation of the non-fiction book Wiseguy,  written by Nicholas Pileggi. Led by Ray Liotta, the film narrates the rise and fall of Lucchese crime family associate Henry Hill over a period from 1955 to 1980. It’s a film that sparked many of our’s passion for film, as the biographical drama tells every detail of Hill’s life. It really is an example of remarkable story telling, and will forever remain as Liotta’s best performance.

* Public Enemies – Johnny Depp as John Dillinger *

The 2009 Michael Mann film, Public Enemies, is an adaptation of Bryan Burrough’s book, Public Enemies: America’s Greatest Crime Wave and the Birth of the FBI, 1933–34. Set during the Great Depression, the film chronicles the final years of the notorious bank robber John Dillinger (Johnny Depp) as he is pursued by FBI agent Melvin Purvis (Christian Bale). Depp has played various gangsters (he stars in three of the films listed in this article), and is set to star in another with the release of Black Mass in November.

* Donnie Brasco – Al Pacino as Lefty Ruggiero *

Based on the true story of Joseph D. Pistone (Johnny Depp), the 1997 film Donnie Brasco tells the story of an FBI undercover agent, under the alias Donnie Brasco, who infiltrated the Mafia Bonanno crime family in New York City during the 1970s, gaining the confidence of hitman Lefty Ruggiero (Al Pacino). This film features another gangster role from Depp, but it is Al Pacino who leads as the real-life gangster Benjamin “Lefty” Ruggiero, who allegedly murdered around 26 people.

* American Gangster – Denzel Washington as Frank Lucas *

A personal favourite, Ridley Scott‘s 2007 biopic American Gangster, follows the criminal career of Frank Lucas (Denzel Washington), a gangster from North Carolina who smuggled heroin into the United States on American service planes returning from the Vietnam War. Washington is absolutely mesmerising in his role here.

* Blow – Johnny Depp as George Jung*

Directed by Ted Demme, Blow is adapted from Bruce Porter’s book Blow: How a Small Town Boy Made $100 Million with the Medellín Cocaine Cartel and Lost It All, and tells the story of American cocaine smuggler George Jung (Johnny Depp). Nicknamed “Boston George”, Jung was a part of the Medellín Cartela and a major player in the cocaine trade in the United States in the 1970s and early 1980s.

* Casino – Robert De Niro as Sam “Ace” Rothstein*

Directed by Martin Scorsese, the 1995 film Casino is based on the non-fiction book of the same name, written by Nicholas Pileggi, and stars Robert De Niro as Sam “Ace” Rothstein, a Jewish-American top gambling handicapper who is called by the Italian Mob to run the fictional Tangiers casino in Las Vegas. His character is loosely based on the career of Frank Rosenthal, who was a professional sports bettor, Las Vegas casino executive, and organized crime associate.

* The Departed – Jack Nicholson as Frank Costello *

Again directed by Martin Scorsese, and a remake of the 2002 Hong Kong film Infernal Affairs, The Departed takes place in Boston and tells the story of Irish Mob boss Francis “Frank” Costello (Jack Nicholson). His character is loosely based on the famous gangster Whitey Bulger (who Johnny Depp will be playing in the upcoming film Black Mass), a former organized crime boss of the Boston Irish mob crew known as the Winter Hill Gang.

* Malcolm X – Delroy Lindo as West Indian Archie *

Spike Lee‘s 1992 biopic Malcolm X sees Denzel Washington lead as Malcolm Little, a hotshot criminal soaking up the guidance of Harlem gangster West Indian Archie (Delroy Lindo). Lindo’s role is only small, but it’s an exceptional performance nonetheless.

* Gangs of New York – Daniel Day-Lewis as Bill The Butcher *

The fourth film in this list directed by Martin Scorsese, the 2002 film Gangs of New York sees Daniel Day-Lewis play crime boss Bill “The Butcher” Cutting. Real name: William Poole, Bill was the leader of the New York City gang Bowery Boys, a bare-knuckle boxer, and a leader of the Know Nothing political movement. Day-Lewis is always brilliant to watch, but he certainly gives another stand-out performance in this.

Set to be released on 9th September, here’s the official synopsis for Legend:

The true story of the rise and fall of London’s most notorious gangsters, Reggie and Ron Kray, both portrayed by Tom Hardy in a double performance. Legend is a classic crime thriller taking us into the secret history of the 1960s and the extraordinary events that secured the infamy of the Kray twins.

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