15 Gangster Movies That Are So Close To Being Perfect Apart From One Key Flaw

Summary

  • Many gangster films fall just short of perfection due to critical flaws like casting decisions or abrupt endings.
  • Eastern Promises offers a powerful exploration of human trafficking but falls short with an unsatisfying conclusion.
  • The Irishman reunites Scorsese, De Niro, and Pacino in a fantastic exploration of Frank Sheeran, but its prolonged runtime and CGI effects distract viewers.

While there have been countless fantastic gangster movies over the years, very few can claim the title of pure perfection and were often held back by one critical flaw. It may be a casting decision, an unnecessary subplot, or a bloated runtime, but there have been so many examples of movies that had perfection within their reach, only for it to be snatched away by one key issue. This does not mean these movies were not great; it’s just that certain issues could be improved upon for them to earn the title of genuinely perfect.

Some of the best gangster movies ever made feel entirely untouchable, as films like the first two Godfather films have consistently been part of the conversation around the best movie ever, regardless of genre. Other releases had everything going for them, but it must be admitted that one aspect held them back from being the perfect version of their story. While some viewers believe it’s blasphemy to criticize some of these classic films, these beloved gangster movies were so close to being perfect, if not for one key flaw that held them back.

15 Eastern Promises (2007)

Directed by David Cronenberg

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Eastern Promises (2007) is a crime thriller directed by David Cronenberg and starring Viggo Mortensen. The film follows a London midwife, played by Naomi Watts, who stumbles upon the underbelly of the Russian mafia while investigating a young girl’s death. Mortensen portrays a mysterious driver with ties to a powerful crime family, unraveling a web of secrecy and corruption. The film explores themes of loyalty, identity, and the immigrant experience.

Director David Cronenberg Release Date September 21, 2007 Writers Steven Knight Cast Viggo Mortensen , Vincent Cassel , Sinéad Cusack , Armin Mueller-Stahl , Naomi Watts Runtime 100 minutes Budget $50 million Main Genre Crime Expand

Director David Cronenberg added his unique voice to the gangster genre with his excellent story of the Russian mob Eastern Promises. Through brutal realism and one of Viggo Mortensen’s greatest performances, this was a powerful exploration of human trafficking and excessive violence that packed a serious emotional punch. However, Eastern Promises also had a rather abrupt ending, with much of the climatic action taking place offscreen. Unfortunately, this resulted in an almost perfect movie feeling somewhat incomplete, as viewers were left wanting more and with several unanswered questions.

14 Boyz N The Hood (1991)

Directed by John Singleton

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Boyz n the Hood, directed by John Singleton, is a 1991 film set in South Central Los Angeles. It follows the lives of three young African-American men—Tre (Cuba Gooding Jr.), Doughboy (Ice Cube), and Ricky (Morris Chestnut)—as they navigate the challenges and pressures of growing up in an environment plagued by violence, gang culture, and socio-economic hardships. The film explores themes of family, friendship, and survival.

Director John Singleton Release Date July 12, 1991 Writers John Singleton Cast Hudhail Al-Amir , Lloyd Avery II , Angela Bassett , Mia Bell , Lexie Bigham , Kenneth A. Brown Runtime 102 minutes

As John Singleton’s directional debut, this first-time filmmaker knocked it out of the park with the powerful social messaging seen in Boyz n the Hood. The urban crime drama shone a light on the violence of street life in disenfranchised African American communities, pioneering the hood film genre and influencing later classics like Training Day. Boyz n the Hood was an incredible drama with amazing casting, including Laurence Fishburne, Cuba Gooding Jr., and Ice Cube, although its social commentary sometimes came at the expense of characterization and narrative depth, which held the film back from being perfect in all respects.

13 Snatch (2000)

Directed by Guy Ritchie

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Snatch is a comedic crime film by director Guy Ritchie that centers on several different groups of characters’ paths that begin to cross after a missing diamond becomes central to their stories. From a fight promoter trying to make pay his bookie to a group of inept bank robbers that fumble a bookkeeping heist, a stolen diamond ends up in the stomach of a dog, setting off a hectic chain of violent but darkly comedic events.

Director Guy Ritchie Release Date January 19, 2001 Studio(s) Sony Distributor(s) Columbia Pictures , Sony Writers Guy Ritchie Cast Benicio Del Toro , Jason Statham , Lennie James , Alan Ford , Stephen Graham , Dennis Farina , Brad Pitt , Vinnie Jones Runtime 102 minutes Budget $10 million Expand

Nobody can make a British gangster film better than Guy Ritchie, whose unique sense of style and powerful aesthetics resulted in crowd-pleasing crime movies with their own brand of humor. Snatch was the perfect example of Ritchie’s talents as a small-time boxer, played by Jason Statham, found himself under the thumb of a ruthless gangster. But it was Brad Pitt as the Irish Traveler Mickey O’Neil who held Snatch back from perfection because, despite giving a solid performance, his Irish accent was genuinely terrible, and he came across more like a parody character than a truly realized person.

12 The Godfather Part III

Directed by Francis Ford Coppola

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The Godfather Part III is the third and final film in Francis Ford Coppola’s Godfather trilogy. The film again focuses on Michael Corleone, who is now in his 60s and looking for his replacement as the head of the family business. While still getting favorable reviews upon release, the film is often considered a significant drop in quality compared to its predecessors.

Director Francis Ford Coppola Release Date December 25, 1990 Studio(s) Paramount Pictures Distributor(s) Paramount Pictures Writers Francis Ford Coppola Cast Al Pacino , Andy Garcia , Diane Keaton Runtime 142minutes Franchise(s) The Godfather Sequel(s) The Godfather Part III prequel(s) The Godfather (1972) Budget $54 million Expand

With two perfect movies already making the Godfather series the most famous gangster franchise of all time, the release of The Godfather Part III had a lot to live up to and unfortunately crumbled amid these incredible expectations. Looking back, all the pieces of a great movie were there, but a rushed script, misguided casting, and a lack of essential characters like Tom Hagen meant The Godfather Part III couldn’t live up to the previous two movies. The Godfather Part III’s one fatal flaw was that it was made for financial reasons rather than the artistry that propagated the previous films.

11 Jackie Brown (1997)

Directed by Quentin Tarantino

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Jackie Brown is a 1997 crime thriller directed by Quentin Tarantino. Pam Grier stars as a flight attendant who outsmarts the authorities, her boss, and a ruthless killer after smuggling cash for a gunrunner. The movie counts with an all-star cast that includes Samuel L. Jackson, Robert De Niro, Robert Forster, Michael Keaton, and Bridget Fonda.

Director Quentin Tarantino Release Date December 25, 1997 Studio(s) MiraMax Distributor(s) MiraMax Writers Quentin Tarantino Cast Bridget Fonda , Michael Keaton , Robert Forster , Pam Grier , Samuel L. Jackson , Robert De Niro Runtime 154 minutes Budget $12 million Expand

Quentin Tarantino paid homage to 1970s blaxploitation cinema with his excellent crime movie Jackie Brown. As Pam Grier’s greatest performance, she played the titular flight attendant-turned-money-smuggler to perfection as Tarantino expanded upon his rich and highly stylized cinematic world. With sharp dialogue, a fantastic cast, and a cool, laid-back style, Jackie Brown had a slower pace than the rest of Tarantino’s work, and although this contributed to its unique feeling, it also meant it never felt quite as urgent as the very best Tarantino movies.

10 American Gangster (2007)

Directed by Ridley Scott

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American Gangster is a 2007 crime film directed by Ridley Scott, featuring Denzel Washington as Frank Lucas, a heroin kingpin in Harlem, and Russell Crowe as Richie Roberts, the detective determined to bring him down. The film explores the rise of Lucas in the drug trade and the eventual intersection of their lives amidst the backdrop of a corrupt and morally complex society.

Director Ridley Scott Release Date November 2, 2007 Writers Steven Zaillian , Mark Jacobson Cast Carla Gugino , Idris Elba , John Hawkes , Cuba Gooding Jr , Russell Crowe , Denzel Washington , Ted Levine , Josh Brolin , Chiwetel Ejiofor , Joe Morton Runtime 157 minutes Budget $100 million Expand

American Gangster stood as one of Ridley Scott’s best movies, as the intense game of cat and mouse between acting legends Russell Crowe and Denzel Washington made for thrilling viewing. However, the attempt to balance Frank Lucas’ (Washington) crime story with Richie Roberts’ (Russell Crowe) made the film feel uneven as it tried to pack too much into an epic true crime narrative. As an engrossing and powerful story that proved Scott could stand toe-to-toe with the best gangster filmmakers out there, American Gangster could have been perfect if it was slightly more streamlined.

9 Touch Of Evil (1958)

Directed by Orson Welles

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After a car bomb detonates at the U.S./Mexico border, Mexican agent Miguel Vargas and American captain Hank Quinlan investigate. As Vargas uncovers corruption within Quinlan’s team, his pursuit of justice jeopardizes his safety and his wife’s, in this tense thriller.

Director Orson Welles Release Date April 23, 1958 Cast Charlton Heston , Janet Leigh , Orson Welles , Joseph Calleia , Akim Tamiroff , Marlene Dietrich , Zsa Zsa Gabor Runtime 111 Minutes

As one of the all-time great directors, Orson Welles proved his talents in the gangster genre with the classic film noir Touch of Evil. This technical masterpiece was badly received when it was first released in 1958, as Welles’ singular vision was tampered with, and Universal executives forced Welles out during post-production (via Guardian.) While Welles’ vision was later restored, and Touch of Evil was re-released in 1998, the damage had been done to its reputation, and for decades, the innovative and emotionally gripping nature of the underrated classic was ignored by general viewers.

8 Gangs Of New York (2002)

Directed by Martin Scorsese

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Gangs of New York, directed by Martin Scorsese, is a historical drama that explores the violent rivalries between immigrant groups in 19th-century New York City. Leonardo DiCaprio stars as Amsterdam Vallon, who returns to the Five Points area seeking revenge against Bill the Butcher, played by Daniel Day-Lewis. The film dramatizes the socio-political unrest in America during that era, highlighting issues like gang warfare and ethnic tension.

Director Martin Scorsese Release Date December 20, 2002 Writers Jay Cocks , Steven Zaillian , Kenneth Lonergan Cast Leonardo DiCaprio , Cameron Diaz , Daniel Day-Lewis , Jim Broadbent , John C. Reilly , Henry Thomas , Liam Neeson , Brendan Gleeson Runtime 167 Minutes Main Genre Drama Expand

As the first collaboration between Martin Scorsese and Leonardo DiCaprio and featuring Daniel Day-Lewis as the iconic villain Bill the Butcher, Gangs of New York had all the makings of modern gangster movie classics. Packed with style and impressive action sequences of rivaling gangster factions, Gangs of New York also suffered from a disjointed narrative and underdeveloped characters. As a highly ambitious project, Gangs of New York tackled too many themes and never provided the space to delve into any of them with the level of depth they required.

7 Lock, Stock And Two Smoking Barrels (1998)

Directed by Guy Ritchie

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Lock, Stock and Two Smoking Barrels is a British crime film directed by Guy Ritchie. Released in 1998, the film follows a group of friends who become embroiled in the London underworld after a high-stakes card game goes wrong. Their attempts to repay a substantial debt lead them into intersecting criminal activities involving a variety of eccentric characters. The ensemble cast includes Jason Flemyng, Dexter Fletcher, Nick Moran, and Jason Statham.

Director Guy Ritchie Release Date August 28, 1998 Studio(s) HandMade Films , SKA Films , The Steve Tisch Company , Summit Entertainment Distributor(s) Gramercy Pictures Writers Guy Ritchie Cast Jason Flemyng , Dexter Fletcher , Nick Moran , Jason Statham , Steven Mackintosh , Vinnie Jones , sting , Peter McNicholl Runtime 106 Minutes Budget $1.4 Million Main Genre Crime Expand

Guy Ritchie proved himself an exciting new voice in British cinema with his gangster classic Lock, Stock and Two Smoking Barrels. With compelling performances from Jason Statham in his acting debut and Vinnie Jones in an intimidating and influential role, Lock, Stock and Two Smoking Barrels felt almost like the British equivalent of a Tarantino movie. While all the pieces of a great film were in place, Lock, Stock and Two Smoking Barrels also featured too many overlapping plotlines and was an unfortunate example of style over substance in terms of narrative heft.

6 The Untouchables (1987)

Directed by Brian De Palma

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The Untouchables, directed by Brian De Palma, is a crime drama set during Prohibition-era Chicago. The film stars Kevin Costner as Eliot Ness, a federal agent determined to bring down the notorious gangster Al Capone, portrayed by Robert De Niro. Alongside Sean Connery as seasoned officer Jim Malone, Ness forms an elite team to combat organized crime, focusing on the legal strategy to dismantle Capone’s empire.

Director Brian De Palma Release Date June 3, 1987 Studio(s) Paramount Pictures Distributor(s) Paramount Pictures Writers David Mamet Cast Kevin Costner , Sean Connery , Charles Martin Smith , Andy Garcia , Robert De Niro , Richard Bradford , Jack Kehoe , Brad Sullivan Runtime 1h 59m Main Genre Crime Expand

The Untouchables was a stylized Prohibition-era gangster movie by Brian De Palma that featured an incredible cast, including Kevin Cosner, Robert De Niro, and Sean Connery. With fantastic action sequences and era-appropriate locations, The Untouchables was a wonderfully entertaining film whose melodramatic dialogue and simplistic good-versus-evil narrative failed to capture the morally conflicted urgency of the best gangster movies. The Untouchables was a very good movie, and if it had leaned more into the gritty realism of its time period, it could have been truly perfect.

5 The Departed (2006)

Directed by Martin Scorsese

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A remake of the 2002 film Infernal Affairs, Martin Scorcese’s The Departed is one of the definitive crime epics. It follows Colin Sullivan (Matt Damon), a Massachusetts State Police officer who serves as an informant for mob boss Frank Costello (Jack Nicholson), and Billy Costigan (Leonardo DiCaprio), an undercover cop placed within Costello’s organization. Both Sullivan and Costigan scramble to uncover the other’s identity in order to save their own lives from the wrath of Costello and his gang.

Director Martin Scorsese Release Date October 6, 2006 Studio(s) Warner Bros. Pictures Distributor(s) Warner Bros. Pictures Writers William Monahan , Alan Mak , Felix Chong Cast Martin Sheen , Matt Damon , Jack Nicholson , Mark Wahlberg , Leonardo DiCaprio Runtime 151 minutes Budget $90 million Main Genre Crime Expand

After more than four decades at the forefront of Hollywood and the gangster genre, Martin Scorsese at last took home the Academy Award for Best Director for his extraordinary epic gangster movie The Departed. With eternal themes of fractured identity, The Departed delved into the world of cops and criminals and the splitting of self when somebody has to live a life undercover. With slow-building tension over nearly three hours, The Departed was a lesson in filmmaking that unfortunately didn’t quite land its chaotic final act, as Billy Costigan’s death felt sudden and unexpected.

4 City Of God (2002)

Directed by Fernando Meirelles and Kátia Lund

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City of God is a Brazilian crime drama directed by Fernando Meirelles and Kátia Lund. Set in the favelas of Rio de Janeiro, the film chronicles the rise of organized crime through the eyes of a young boy named Rocket. As Rocket grapples with the harsh realities of his surroundings, the film explores themes of poverty, violence, and survival, offering a poignant and unflinching look at the impact of crime on a community.

Director Fernando Meirelles , Kátia Lund Release Date February 13, 2004 Writers Paulo Lins , Bráulio Mantovani Cast Alexandre Rodrigues , Leandro Firmino , Matheus Nachtergaele , Phellipe Haagensen , Douglas Silva , Jonathan Haagensen , Seu Jorge , Jefechander Suplino Runtime 130 Minutes Main Genre Crime Expand

While many of the most famous gangster movies of all time were American or British-made, it’s important not to disregard all the fantastic gangster films from filmmakers across the globe. One of the best international gangster movies was the Brazilian film City of God, which powerfully depicted organized crime in the suburbs of Rio de Janeiro. With rapid pacing and intense violence, the over-the-top nature of City of God at times overloaded the movie’s emotional weight and could be criticized for presenting a glorified view of poverty-stricken communities that made a life of crime look oddly enticing.

3 Mean Streets (1973)

Directed by Martin Scorsese

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Mean Streets is a crime drama directed by Martin Scorsese, following the lives of small-time criminals in New York City’s Little Italy. Starring Harvey Keitel as Charlie and Robert De Niro as the reckless Johnny Boy, the film explores themes of guilt, redemption, and the harsh realities of street life. Mean Streets is noted for its gritty portrayal of urban corruption and the dilemmas faced by those entangled in it.

Director Martin Scorsese Release Date October 14, 1973 Writers Martin Scorsese , Mardik Martin Cast Robert De Niro , Harvey Keitel , David Proval , Amy Robinson , Richard Romanus , Cesare Danova , Victor Argo , George Memmoli Runtime 112 Minutes Main Genre Crime Expand

Mean Streets was the movie where director Martin Scorsese finally figured out his unique style, and all the pieces came together to create an impressive, cohesive whole. However, Mean Streets also lacked the depth of Scorsese’s best gangster movies, and although it laid the groundwork for the most pressing themes of his career, he would later expand and improve upon the tenets set out here. Mean Streets was a truly great movie, but it would take some time before Scorsese made a perfect gangster film with the release of Goodfellas in 1990.

2 Once Upon A Time in America (1984)

Directed by Sergio Leone

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Once Upon a Time in America tells the story of a group of Jewish gangsters in New York City over several decades, from their youth in the 1920s to their final days in the 1960s. Robert De Niro and James Woods star in the 1984 crime drama directed by Sergio Leone.

Director Sergio Leone Release Date June 1, 1984 Studio(s) Warner Bros. Pictures Distributor(s) Warner Bros. Pictures Writers Harry Grey , Leonardo Benvenuti , Piero De Bernardi , Enrico Medioli , Franco Arcalli , Franco Ferrini , Stuart Kaminsky , Sergio Leone Cast Robert De Niro , James Woods , Elizabeth McGovern , Treat Williams , Tuesday Weld , Burt Young , Joe Pesci , Danny Aiello Runtime 229 Minutes Budget $30 million Main Genre Crime Expand

The iconic director of the Spaghetti Western genre, Sergio Leone, tried his hand at an epic, sprawling narrative that traversed generations with Once Upon a Time in America. At almost four and a half hours in length in its original cut, this ambitious story of two Jewish gangsters’ rise in New York’s organized crime scene was told out of chronological order and had significant content cut from its American release, which stood at 139 minutes. With many versions of varying quality, Once Upon a Time in America can be a cinematic masterpiece or a convoluted mess, depending on the cut.

1 The Irishman (2019)

Directed by Martin Scorsese

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Based on the nonfiction book “I Heard You Paint Houses” by Charles Brandt, The Irishman follows Frank Sheeran and his time working for the Italian mafia. In recounting his past, the mob hitman recalls his possible involvement with the slaying of Jimmy Hoffa.

Director Martin Scorsese Release Date November 27, 2019 Studio(s) Netflix Distributor(s) Netflix Writers Steven Zaillian Cast Bobby Cannavale , Jack Huston , Joe Pesci , Jesse Plemons , Sebastian Maniscalco , Al Pacino , Kathrine Narducci , Stephen Graham , Ray Romano , Aleksa Palladino , Anna Paquin , Robert De Niro , Harvey Keitel , Jake Hoffman Runtime 210 minutes Budget $200 million Expand

To see the iconic director of some of the best gangster movies ever, Martin Scorsese, reunite with Robert De Niro and work with Al Pacino was always going to be a cinematic treat. The result was the fantastic exploration of gangster Frank Sheeran that even the most devoted viewers would admit was overlong as the runtime of The Irishman stood at a whopping 209 minutes. Adding to this, the de-aging CGI effects on De Niro and Pacino were slightly distracting as Netflix viewers became more focused on the technical aspects of The Irishman than its compelling narrative.

Source: Guardian