12 Best Movies Based on Real Life Gangsters

Mobsters and mafia in movies are somehow portrayed as cool. However, we enjoy these films in the safety of our own homes, never having been exposed to the actual violence of gangs. The victims sometimes speak of the horrors they experienced firsthand and even despise such movies sometimes. However, for the audiences far removed from said concerns, we can enjoy gangster films, and we enjoy them even more if they are based on real-life gangsters – we can just picture them strutting in, owning the place, and not giving two hoots about anyone else. Here is the list of top movies based on real-life mobsters.

12. Pain & Gain (2013)

Michael Bay directed this dark comedy, and it appears on the list because although the people weren’t part of any official gang or gangsters, the bodybuilders in the Sun Gym did form a kidnapping ring and things really did go awfully wrong for them. The number of snags they hit on the way is what inspired Bay to make the dark comedy in the first place. Although the victim’s family was displeased with the perpetrators being made to look like sympathetic goofballs, the film itself is a laugh riot and deserves a watch. A little sneak peek – the part where the chainsaw gets clogged due to hair, is actually derivative of the real incident where the chainsaw wouldn’t work because they forgot to put motor oil in it.

11. Hoodlum (1997)

The film, directed by Bill Duke, is set in a very volatile time in New York crime history. The film presents a fictional account of the actual gang war between an Italian and Jewish alliance and the black gangs in Harlem. Heading the black gangs was Ellsworth ‘Bumpy’ Johnson, who was played excellently by Lawrence Fishburne. The alliance was headed by the dreaded duo Dutch Schultz, played by Tim Roth, and Lucky Luciano, played by Andy Garcia. Hosting a gallery of rogues, the film made use of the excellent acting talents to make this gangland violence movie a success. Watch out for Tim Roth and Lawrence Fishburne’s performances, especially in this movie; they are very good!

10. Blow (2001)

This fantastic true crime story is based on the real-life story of George Jung a young boy who was convicted of marijuana dealing but later went on to become one of the largest cocaine dealers in the USA. Jung is played to perfection by Johnny Depp, but a movie about cocaine during that time is a movie where there will be a presence of the Medellin cartel, and we get to see a fine cinematic portrayal of Pablo Escobar. Note that this was long before Narcos and Wagner Moura blew us away. Cliff Curtis as Pablo Escobar in this film was very memorable and he easily filled the role of the formidable gangster and feared boss of the Medellin cartel.

9. Legend (2015)

This crime thriller is a recent addition to a list of fine films based on real-life gangsters. The Kray twins were violent gangsters who controlled most of London’s east end, including a lot of gambling operations and a few nightclubs. Portrayed by Tom Hardy in a double role, Ron and Reggie Kray come to life before us on screen – all their rage, all their violence, all of Reggie’s mental instabilities are brought forth expertly under Hardy’s exquisite acting potential. This film was rather underrated when it was released, but it deserves a lot more attention and is a fine gangster movie in itself.

8. Black Mass (2015)

This year was a good year for movies on real-life gangsters and here is another. James Whitey Bulger, a feared head of the Irish mob that ran in South Boston. Played by Johnny Depp, who should get top marks for makeup and acting, the film focuses on Bulger’s alliance with the FBI and the subsequent misuse of the alliance to further his criminal empire. Bulger’s notoriety is captured brilliantly by Depp, who makes the menace evident in a few high-tension scenes. A fantastic movie, Depp truly brings the feared Irish mob boss to the screen brilliantly.

7. Donnie Brasco (1997)

Perhaps one of the greatest undercover stories, this film, directed by Mike Newell, is based on the real-life infiltration of the Bonnano crime family. Johnny Depp plays an FBI agent here whose alias is Donnie Brasco. He develops a friendship with Lefty Ruggerio, a soldier for the family. Ruggerio, a feared enforcer, had around twenty-six murders to his name and was an old-school Cosa Nostra mobster. A man who would not break the rule of Omerta even when captured. Al Pacino brings the character to life brilliantly – showing the human side of the job and the allegiance to the family. Pacino brings to screen all of the acumen of Mafia politics that Ruggerio had and gives us a very real representation of the soldier’s life.

Read More: True Crime Stories

6. American Gangster (2007)

Directed by Ridley Scott, the film stars Denzel Washington as Frank Lucas, the dreaded drug dealer who used to be the right-hand man of Bumpy Johnson, the man who later on partnered with the feared Lucky Luciano. Lucas’ rise to power and dealing with the old order of the New York Five Families is portrayed in a typical Hollywood style, with embellishments and exaggerations. However, Washington’s portrayal of Lucas as he navigates a crime-addled empire and remnants of racial and post-war tensions makes the film a truly spectacular watch.

5. Casino (1995)

Directed by Martin Scorsese, the film explores the outreach of the Mafia in Las Vegas during its formative days. Starring Robert De Niro and Joe Pesci, the film is a gripping tale of a friendship that devolves under the strain of building Vegas. The character of Rothstein played by De Niro was based on the real-life character of Rosenthal a wizard at analyzing most games and a member of the Chicago mob outfit. Pesci’s character is a made man based on the real-life gangster Anthony Spilotro. Scorsese tries to stay as true to the story as possible including some of the execution styles as well, making this movie a brilliant watch for those interested in mob history, and it’s a Scorsese film so I won’t even go into why cinephiles should watch it.

4. The Untouchables (1987)

Directed by Brian De Palma the film is a Hollywood retelling of the great takedown of the Chicago mobster Al Capone, on tax evasion. Sporting a strong cast which included Kevin Costner as Eliot Ness, Sean Connery and Robert De Niro and Billy Drago as Al Capone and Frank Nitti respectively. The brilliance of the film is in the acting, the pervasive menace of Al Capone’s character and De Niro channels it brilliantly – from the apologetic barber who nicks him while shaving to the press being brazenly told that alcohol served in his house during Prohibition wasn’t bootlegging, it was hospitality. Nitti’s cold calculated role is captured by Drago, whose understated nature next to De Niro’s performance was exactly like the relationship between Nitti and Capone, the cold mobster eventually replaced Capone as the head of the Chicago Outfit when he was imprisoned.

3. Goodfellas (1990)

Another film by Martin Scorsese and based on Nicholas Pillegi’s book ‘Wiseguy’ based on the real-life story of Henry Hill, his rise to power and his eventual move to witness protection to escape the wrath of the mob and the closing authorities. Henry Hill is played by Ray Liotta who brings an explosive intensity to the role, much like the real-life Henry who truly did believe that gangsters were above normal people and loved the way of life. De Niro appears once again as Jimmy Conway based on the character of Jimmy Burke. Both Liotta and De Niro’s commitment to the role is evident – De Niro called Hill multiple times to figure out how Jimmy walked, talked or held his cigarette and for Liotta’s part- he heard FBI cassettes to get Hill’s voice down to a notch. An excellently made film and perhaps one of the best gangster movies we have had the pleasure of watching, the film remains an insightful and pleasurable documentation of a part of the Lucchese crime family.

2. Public Enemies (2009)

Directed by Michael Mann, the film traces the life and exploits of notorious gangster John Dillinger and his crew which included infamous names like Baby Face Nelson. The film has an impressive cast including Johnny Depp as Dillinger, Stephen Graham as Baby Face and the talented Christian Bale cast as FBI agent Melvin Purvis. The movie follows the FBI trying to catch Dillinger, and the brilliant acting from Depp brings this role to life – a man who was always above the law and a man who flouted society every step of the way. The charm, the notoriety and the ruthlessness of Dillinger are brought to life in this movie excellently.

1. Gangs of New York (2002)

Directed by Martin Scorsese this is a fantastic film that explores the street gang culture in New York set before the Civil War. Including a very strong cast amongst whom were Leonardo DiCaprio and Daniel Day-Lewis, the film has been praised for its raw intensity and the fantastic acting is a large part of it. Day-Lewis’ method acting really channels Bill the Butcher who was based on William Poole. Scorsese in his thoroughness keeps the major details same – Bill running a meat shop, being a pugilist and having dealings with Tammany Hall. A fantastic story about old days of America, this has to be one of the finest representations of a real-life gangster that we have had the privilege of seeing thanks to Martin Scorsese and Daniel Day-Lewis.

Read More: Gangster Movies

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