20. The Gentlemen (2019)
When thinking of gangsters, two images might come to mind: the hat-and-trench-coat-wearing cigar smokers of Prohibition, or the tracksuit-wearing weed smokers who flex on the streets.
The Gentlemenpresents us gangster types who are somewhere in between. Although Colin Farrell does rock a tartan tracksuit as Coach, most of the other characters wear fine suits and drink whiskey.
They’re “gentlemen gangsters,” so to speak.
While Coach’s students are stupidly making a music video at a crime scene, Ray (Charlie Hunnam) whips out a machine gun to teach some wannabe roadmen gangsters some humility.
Apart from Matthew McConaughey,The Gentlemenprides itself on being distinctively British and distinctively Guy Ritchie.
Related:The Best British Gangster Films of All Time, Ranked
19. Donnie Brasco (1997)
Johnny Depp has appeared in several mobster movies—most notablyPublic EnemiesandBlack Mass—but his best appearance came alongside Al Pacino inDonnie Brasco.
Many gangster movies take the undercover angle, where officers must convincingly infiltrate a dangerous gang. This keeps us on our toes for every near-miss mistake that could blow their cover.
But this one’s even more tense since Donnie Brasco was arealundercover cop who made it into the Mafia during the 1970s, exemplifying the adage of “fake it ‘til you make it.”
Mike Newell adapted the nonfiction book into a two-hour drama that dodges the usual criminal tropes you might expect.
18. American Gangster (2007)
Criminal organizations take a lot of, well, organizing. The most successful ones involve tons of people, jobs, bribes, secrets, fights, meetings, rigs, robberies, etc.
In 1968, Frank Lucas decided to cut out the middleman and deal with his heroin source directly—like any true businessman would. After all, Frank Lucas was a real-life corporate guy.
He’s played by Denzel Washington in Ridley Scott’sAmerican Gangster, going up against detective Richie Roberts (Russell Crowe).
While most of Harlem takes Lucas at face value when he fronts as a businessman striking connections with politicians, Roberts sees through it and works to bring him down.
Although not entirely accurate (Roberts took issue with Washington’s “noble” portrayal of Lucas),American Gangsteris a gripping watch thanks to Ridley Scott’s expert dramatization.
17. The Long Good Friday (1980)
Most British crime films feature Cockney gangsters. There’s just something about the accent and their want for London domination.
The London setting is crucial inThe Long Good Friday, which serves as a backdrop to the politics of the era, all of which is expertly woven throughout the film by director John Mackenzie.
Bob Hoskins is Harold Shand, a gangster trying to go legit. The corruption of cops and politicians help, as he’s able to strike deals and make plans to redevelop the London Docklands.
Then, bombs go off. Friends are murdered. Harold has to chuck it all in to find the culprit, and he has to do it all without showing any cracks or blind spots in his growing business.
The watertight plot and Hoskins’s “sinister” performance putThe Long Good Fridayup there with Britain’s best gang movies.
16. Eastern Promises (2007)
Gangsters are a hard bunch, but Russian gangsters are something else.Eastern Promisesdepicts the Russian mafia in London as they’re approached by Anna (Naomi Watts), despite being warned not to.
After delivering the baby of a 14-year-old prostitute—who dies giving birth—Anna tries to track down the girl’s family using her diary. This diary leads her straight to the doorstep of Nikolai Luzhin, whose tattoos and Russian accent speak to his mafia status.
Viggo Mortensen gives a chilling performance as the violent, man-of-few-words mobster, made all the more real by his study of Russian gangs and symbology before filming.
The psychological aspect ofEastern Promisesis what differentiates it from most action-based crime flicks. David Cronenberg directs this brooding drama that isn’t afraid to outsmart its viewers.
Related:The Best Years for Movies: Which Years Were Stacked With Great Films?
15. Lock, Stock and Two Smoking Barrels (1998)
Circling back to Guy Ritchie,Lock, Stock and Two Smoking Barrelsputs the comedy in crime via Ritchie’s usual style of dark humor.
Although Ritchie’sSnatchis more well-known for its tapestry of criminal plotlines and characters, everything that madeSnatchgreat can first be found inLock, Stock and Two Smoking Barrels.
Ritchie laid the foundations for his trademark collaborations, criminal themes, fast-paced filming, and British slang/humor (where everyone seems to have a nickname) in his feature debut.
Of these collaborations, Vinnie Jones, Jason Statham, Jason Flemyng, and Alan Ford all appear inLock, Stock and Two Smoking Barrels. Sting is also in there, somewhere.
This one isn’t just a gangster movie—it’s also a heist movie! And it’s all awash in themes of masculinity, patriotism, power, loyalty, and revenge, presented with a rough-and-tumble sheen.
Related:The Best Caper Movies of All Time, Ranked
14. Reservoir Dogs (1992)
An independent cult neo-noir? That might sound like one for the cinephiles, butReservoir Dogsseems to be popular with everyone. Quentin Tarantino’s feature debut was a hit—to say the least—and it only got more popular after the release ofPulp Fiction.
Gangsters love nicknames, but these guys take it to another level by adopting secret color aliases: Mr. Brown, Mr. White, Mr. Blonde, Mr. Blue, Mr. Orange, and Mr. Pink.
Reservoir Dogsdepicts a gang trying to pull off a heist that inevitably goes wrong, but soundtrack dissonance, deadpan jokes, trivial conversations, and a Mexican standoff setReservoir Dogsapart as one of the most unique crime movies in the genre.
Harvey Keitel, Tim Roth, Chris Penn, Steve Buscemi, and Michael Madsen make their first of several Tarantino movie appearances, alongside the director himself as Mr. Brown.
13. Casino (1995)
If there’s one person to rule the gangster genre, it’s Robert De Niro—usually under the direction of Martin Scorsese.
The acclaimed director grew up in Little Italy of New York City back during the Mafia’s “golden age,” so he witnessed the gangster lifestyle first-hand, albeit from a distance.
You’ll notice that Martin Scorsese’s mobster movies often go beyond gang warfare and into family dynamics, friendship, culture, loyalty, guilt, and religion (specifically Catholicism).
That’s what makes them so great—alongside strong casts and dynamic camerawork—and it’s a direct result of his childhood observations.
Scorsese’s first gangster flickMean Streetsmarked the dawn of New Hollywood’s greatest crime duo: De Niro and Scorsese. They got together with Joe Pesci forCasino, and later again forThe Irishman.
The Chicago Outfit is a huge Italian-American crime syndicate (formerly led by Al Capone) that, inCasino, asks a gambling expert to oversee a casino in Las Vegas. Although he starts off doubling profits, working under the Mafia’s eye proves a difficult task.
Related:The Best Movies About Gambling and Casinos, Ranked
11. Get Carter (1971)
Mike Hodges’s directorial debutGet Carterended up becoming an emblem of 1970s British cinema.
Known for his anti-heroic characters and sarcastic humor, Michael Caine had already established himself as the go-to Cockney casting choice for his work in the infamous caper filmThe Italian Job.
Caine came on board as another criminal inGet Carter, but this time he was an official London gangster returning to Newcastle to investigate his brother’s murder.
Jack Carter isn’t a trained detective, but his history in organized crime has sharpened his senses to foul play. And even though he’s the protagonist, Carter is a truly terrible person, resulting in a blatantly amoral movie that was praised for its soulless realism.
12. A Prophet (2009)
French cinema has some truly great crime movies, fromLa HainetoPurple Noon. There’s alsoA Prophet, which takes us off the streets and into prison, where 19-year-old Malik El Djebena (Tahar Rahim) is taken in by the Corsican Mafia.
Generally, prison is supposed to rehabilitate inmates and prevent further crime. But inA Prophet, Malik enters as a petty criminal and leaves as a high-ranking assassin.
What else is there to do in prison except learn new skills?
As Malik rises through the ranks to become a respected member of the mob, director Jacques Audiard grabs us from the start and holds us captive with this character-driven prison drama.
Related:The Best Movies About Prison, Convicts, and Death Row
10. Tokyo Drifter (1966)
Leaving the criminal life behind is easier said than done—once you’re in the game, you’re effectively in it forever.
“Phoenix Tetsu” Hondo didn’t ask to quit the game, though. His boss just up and left, leaving Tetsu to wander around Tokyo, ducking rival gangs like a deadly game of dodgeball.
That said, it’s a lifestyle he ends up quite attached to.
Seijun Suzuki’s yakuza film starring Tetsuya Watari as hitman-turned-vagrant is a bold and poppy crime flick, filmed in crazy camera angles. Looking for an Asian gangster flick? It’s one of the best.
Sadly, Suzuki was fired by Nikkatsu not long after releasingTokyo Drifter. As wild and wonderful as it is, the company had been warning Suzuki to tone down his work for a while—and he refused.
9. The Departed (2006)
Martin Scorsese is one of the few filmmakers who can actually turn a reboot into something better. He did it first withCape Fear, then again withThe Departedmany years later.
The critically acclaimed Hong Kong original—titledInfernal Affairs—didn’t seem like one that needed an English-language remake. People feared that it would butcher the original’s emotional depth.
But Martin Scorsese knows what he’s doing. In collaboration with one of his favorites, Leonardo DiCaprio, he went ahead and basedThe Departedon real corrupt agents and Irish mob bosses.
The Departedtakes your standard undercover cop plot and doubles it: while MSP trooper Billy Costigan is trying to infiltrate a Boston gang, the gang’s leader has already planted his own spy within the MSP.
The complex plot is brought to life by a star-studded cast that includes Matt Damon, Jack Nicholson, Mark Wahlberg, Martin Sheen, Ray Winstone, Vera Farmiga, and Alec Baldwin.
Related:Brilliant Movies With Symbolism That Elevate Their Stories
8. Scarface (1983)
Did you know that Brian De Palma’sScarfacewas actually a semi-remake of the 1932 pre-CodeScarfaceby Howard Hawks?
Hawks had based his film on Armitage Trail’s novel, which in turn was based on the life of Al Capone, who was nicknamed “Scarface.”
Brian De Palma took that basic framework and remodeled it into a Hollywood movie. Set in the 1980s, we now have Tony Montana (instead of Al Capone) selling illegal substances and getting charged with tax evasion.
Profanely portrayed by Al Pacino, Tony is a Cuban refugee who starts working for a drug lord in exchange for a green card. The indulgent three-hour runtime is worth it for that grand finale.
Related:The Best Movie Posters of All Time (That Are Iconic and Famous)
7. Gomorrah (2008)
How about some Italian gangsters? Not the New York variety—we’re talking real mobsters from Italy. The Casalesi clan is a subsection of the Camorra criminal society operating between Naples and Latium.
Roberto Saviano wrote about the Casalesi in his nonfiction bookGomorrah, and his involvement in the film adaptation is partly whyGomorrahis so good!
Gomorrahtakes us through the lives of five separate characters affected by gang warfare in Naples. It took six writers to weave it all together: Maurizio Braucci, Ugo Chiti, Gianni Di Gregorio, and Massimo Gaudioso, alongside Saviano and director Matteo Garrone.
The street rivalries aren’t just surface level in this New Italian Epic. Matteo Garrone probes deeper to show the full scale of organized crime, with tendrils that spread low and wide below society.
6. Once Upon a Time in America (1984)
Once Upon a Time in Americais the third installment in Sergio Leone’s “Once Upon a Time” trilogy, which all share similar titles but are otherwise unrelated.
Set in 1918, street kids named Noodles, Patsy, Cockeye, and Dominic are committing petty crimes for a guy called Bugsy. Fifteen years later, they’re adults who are practically running Manhattan thanks to bootleg liquor profits during Prohibition.
Although it’s now considered among the greatest gangster movies ever made,Once Upon a Time in Americawas initially met with nonchalance and a distinct lack of Oscar nominations.
If you’re a hardcore Robert De Niro fan, there’s an Extended Cut that stretches over four hours for your enjoyment. It was originally intended to be two movies, but Leone fused them into one big film—and then Warner Bros. shortened it without Leone’s supervision…
5. Boyz N the Hood (1991)
Most of these movies take place back in the day, with old-school mobsters making up the bulk of cinema’s greatest gang films.Boyz N the Hood, however, is all about 90s urban gang culture.
Once upon a time in South Central LA, young Tre is sent to live with his tough-loving father. Despite the rough neighborhood, Tre grows into a respectable young man… until his old friends return from prison.
Cuba Gooding Jr., Ice Cube, Morris Chestnut, and Laurence Fishburne star in what was supposed to be a script for film school application, but turned into an Oscar-winning classic that launched careers and changed cinema forever.
Director John Singleton became the first African American—and youngest person—to get an Oscar nomination for Best Director, thanks to this poignant coming-of-age drama.
Related:The Best Hood Movies That Are More Than Urban Stereotypes
4. The Public Enemy (1931)
The Public Enemywasn’t just set during the era of Al Capone and speakeasies—it was made during it!
The early 1930s saw Hollywood take over the film industry and become dominated by big studios, drifting in a kind of limbo phase between “talkies” and censorship laws.
Set in Chicago, a hotbed for Prohibition-era mobsters, Tom Powers and Matt Doyle climb the ladder from poverty to bootlegged riches. They credit their success to “beer and blood” (which is the title of the unpublished novelThe Public Enemywas based on).
The Public Enemyis a gangster-versus-law narrative, rather than the typical gang-versus-gang story of the time. Critics weren’t overly fond of its glorification of crime, but that’s not much of an issue nowadays.
Related:The Best Pre-Code Hollywood Movies Still Worth Watching
3. The Godfather (1972)
It’s hard to pick just one film from this legendary trilogy… so even if I’m going with the first, it’s really a stand-in for the entire series.The Godfatheris best appreciated in its full form, anyway.
Adapted from Mario Puzo’s 1969 novel,The Godfathermovies center on the Corleone crime family, for whom loyalty means everything.
Marlon Brando leads the family as Vito Corleone, a Sicilian orphan and immigrant who builds his empire from scratch. Vito has four children, with Michael (Al Pacino) next in line for the throne.
Francis Ford Coppola’s Oscar-winning trilogy is in the top five of pretty much any mainstream “best movies” list. The complex storyline, high-caliber acting, symbolic cinematography, and keen character development all make for a cinematic masterpiece.
Related:The Best Scenes From The Godfather Movies, Ranked
2. City of God (2002)
City of Godmight just be the least glamorized gangster movie on our list. The savagely vicious gangs in Cidade de Deus makeThe Gentlemenlook like a tea party.
Plus, this one’s based on a real period of time when warfare in Rio was at its peak—and the filmmakers made the brave decision to shoot on-location (using locals instead of actors).
Fernando Meirelles and Kátia Lund direct this Brazilian crime epic that’s not for the faint-hearted. We witness Rio’s gang culture through the eyes of Rocket (Alexandre Rodrigues), a young wannabe photographer who captures the events on his camera and narrates the movie.
City of Godis a raw and bloody-nosed depiction of poverty and what it can lead to, made all the more astounding by the fact it even got made at all. (That said, some Brazilian critics disliked howCity of Godreduced the favela down to pure violence.)
Related:The Best Movies About Poverty and Homelessness, Ranked
1. Goodfellas (1990)
Did you know Martin Scorsese was reluctant to make yet another gangster film when he was planningGoodfellas? It ended up being the most famous gangster movie of all time.
Robert De Niro is at the forefront in one of his most iconic roles, alongside Ray Liotta and Joe Pesci (with his notoriously improvised “Funny how?” scene).
Set between the 1950s and 1980s,Goodfellasis the rise-and-fall story that tops them all. The long takes and candid dialogue give us a peek into the everyday life of a mafia man as he saunters from nightclubs to drug deals to family dinners.
Goodfellasis the epitome of Scorsese’s trademarks, as if all his other gangster films were just practice for this one. It’s the perfect balance between naturalism, entertainment, and craftsmanship!
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