They know how to wield a gun, intimidate and take care of their own, all with an air of professionalism (to varying degree). We speak of course of the stars and supporting cast of gangster movies; the organized crime families and the men of law who pursue them.
Killing fellow criminals is one thing, but for those entrepreneurial souls ready to build an empire in society’s margins – and defend it at all costs – their struggle for greatness and eventual fall is the stuff moviegoers yearn for.
How will the star-studded cast of this week’s Gangster Squad stack up against the films that came before? We thought we’d look back to see just how far the bar has been raised on gangster movies over the years.
The genre is a massive one, but here’s our list of the 10 Best Gangster Movies – In no particular order.
Al Capone: the undeniable king of Prohibition-era Chicago with cops and public officials in his pocket. Enter the Bureau of Prohibition agent Eliot Ness, and his handpicked team from every branch of law enforcement, intent on hitting Capone where it hurts: his bank accounts. Publicize Capone’s useless attempts to buy them off, and they’ve even got a name – The Untouchables.
Ness’ autobiographical account of the same name spawned several spin-offs, but Brian De Palma’s film adaptation with Kevin Costner as Ness and Robert De Niro embodying Capone is a classic. Not just because of the cast assembled for the film, but for exploring how much good men can do in the name of law and order – and that famous train station shootout scene.
While The Untouchables may seem to have much in common with Gangster Squad, for us, De Palma’s handpicked team of lawmen turning the tables on the mob is…beyond compare.
The story is one that would be made up, if it hadn’t already happened. Based on the autobiography of FBI agent Joseph Pistone, Donnie Brasco follows Johnny Depp as the titular agent, taken under the wing of Lefty Ruggiero (Al Pacino) for a six-year undercover infiltration of New York’s Bonanno crime family. It was an investigation that led to Brasco almost becoming a made man, and resulted in over 100 criminal convictions.
Normally, watching Al Pacino and Johnny Depp chew scenery at the top of their respective games would make any movie worth watching on its own, but the grounded approach and truly gut-wrenching drama and suspense make Donnie Brasco an exercise in restraint. Where Brasco ends and Pistone begin is a compicated question by the end, and the film does it justice.
Gangster movies, or tales of undercover operations, tend to feature at least some instances of betrayal, risk, and questions of identity. But Donnie Brasco makes those issues its sole priority.
An organized crime family plants one of their own into the police force, while an undercover officer manages to infiltrate the crime family simultaneously. The inevitable eventually happens, as both moles seek out the other among friends and betrayed associates.
That’s the premise of Wai-keung Lau’s Infernal Affairs – a film strong enough to not only prove that Honk Kong cinema is still a hotbed of creativity, but that Martin Scorsese could win his first Best Picture Oscar for the Infernal Affairs remake known as The Departed. The movies aren’t identical, but it’s the story they share that cements their spot on our list – along with the talent assembled for both films.
These flicks each offer a thrilling look at the stress and toll that living a life of secrecy takes on even the best of men, and the broken line between good and bad.
As one of the directors responsible for (almost single-handedly) creating the ‘spaghetti western’ genre of films, it should come as no surprise that Sergio Leone’s tale of Prohibition-era America should be just as influential.
Casting Robert De Niro as David “Noodles” Aaronson, Once Upon a Time in America chronicles the lives of both he and his fellow Jewish-ghetto-dwelling friends in 1920s Manhattan up through 1968. With a story spanning fifty years and following the boys’ rise from small-time thugs to mob pawns, the epic tale of love, friendship, betrayal, violence, and ambition leaves few stones in the road to the ‘American dream’ unturned.
…And we do mean ‘epic.’ There’s a good chance that even fans of the film have not yet seen it the way Leone intended, as his original cut ran 269 minutes long. At present, Martin Scorsese continues to work with Leone’s family to compile a complete, definitive print.
We could say that just having Tom Hanks portraying Irish mob hitman Michael Sullivan makes Road to Perdition one of our favorites; luckily, the rest of the cast and the emotional ground it walks are just as inspired. The Prohibition-era setting is familiar, but themes of fatherhood, family, and vengeance steal the show.
Director Sam Mendes was looking for a story that would say more with images than words, so adapting Perdition from the graphic novel of the same name makes sense. And the imagery didn’t disappoint, as the “less is more” mentality that shapes the film’s visuals earned Conrad Hall a posthumous Academy Award for Best Cinematography.
The film isn’t only memorable for Paul Newman’s last onscreen role (for which he earned a Best Supporting Actor nomination); it’s memorable for being one of the best movies ever adapted from a graphic novel.
The perversion of the American Dream that was Brian De Palma’s Scarface is one that has stood the test of time in the film industry, and not because it adorns the walls of approximately half the college dorm rooms in America. Following Cuban refugee Tony Montana in his ascent (and, you guessed it, downfall) due to organized crime and the drug trade, the film may have been hotly debated when it was released in 1983, but has since cemented its spot among the world’s best gangster films.
Over-the-top violence, a protagonist that the viewer can at once relate to, despise, and pity, and Pacino again delivering a stellar performance (with some help from his little friend) all make Scarface an undeniable classic.
It may be the most gruesome and unapologetic of the films on our list, but it tells a story that few directors ever attempted – and does so beautifully.
For decades, actor James Cagney was synonymous with ‘gangster,’ and rightly so. Portraying the scoff-law as something more than merely a criminal, none of Cagney’s films better illustrates the modern-day rebel and revolutionary of the fedora-donned gangster than The Public Enemy.
Based on the novel “Beer and Blood” by two real-life henchmen, the initial release of The Public Enemy was met with mixed reactions from critics, who claimed that the film was either a new benchmark for gangster movies, or simply another entry in the genre. What wasn’t disputed was Cagney’s performance as one of the most unlikable, offensive and downright nasty career criminals the screen had seen.
Harsh and unkind towards not just his family, but the women in his life (via the infamous ‘grapefruit scene’), Cagney helped deliver a gangster film that would be immortalized, so audiences could forever detest ‘Tom Powers.’
Ray Liotta may not be the name that comes to mind when the term ‘gangster’ is thrown around, but as Goodfellas‘ protagonist Henry Hill, being welcomed into the Lucchese crime family was all he’d ever wanted. Aided by Robert De Niro and Joe Pesci, the trio’s ventures into heists, drugs, and everything in between is regarded as one of the best movies ever, period.
Based on the non-fiction novel “Wiseguy” by Nicholas Pileggi – the book director Martin Scorsese claimed he’d been waiting for “my entire life” – Goodfellas distinguishes itself as a story not of the most famous or feared mobster in history, or the most infamous crimes, but of the mundanities of mob life in addition to the excitement.
Henry’s rise from a goodhearted kid looking for a larger family and purpose, all the way through big-time robberies and drug use, is as unrelenting as it is captivating. Scorsese may not have been done with the gangster genre, but few other films on our list can truly be compared with Goodfellas, Scorsese’s “mob home movie.”
Miller’s Crossing‘s strengths could be summed up by simply saying that the film is the Coen Brothers at their best – the fact that it’s a gangster movie is merely an added bonus to fans of the genre. Following the relationship between mob angler/confidant Tom Reagan (Gabriel Byrne) and his boss Leo O’Bannon (Albert Finney) as war breaks out between rival Irish and Italian gangs in one small town, the combination of gangster movie and noir film tropes results in a story almost universally praised.
Drawing from the detective stories of Dashiell Hammett and the Coen Brothers’ endless supply of enigmatic filmmaking techniques, Miller’s Crossing has a script and cast that few films ever enjoy, despite it being a box office failure.
Byrne and Finney own the bulk of the story, but the performance turned in by John Turturro is truly one for the ages. It may not feature quite as much machine-gun fire or violence as our other favorite gangster films, but its dissection of the genre deserves as much praise as we can give it.
Mario Puzo’s novel “The Godfather” is due nearly as much credit for the gangster genre as any film, as it familiarized the public with terms like “consiglieri” and “Cosa Nostra” and showed that gangster stories and a criticism of the American Dream walked hand-in-hand. Of course, it was Francis Ford Coppola’s adaptation of The Godfather, that made Don Vito Corleone (Marlon Brando) a household name, and the story of the Corleone family one of the greatest ever told on screen.
There’s little to say about The Godfather that hasn’t been already, but suffice to say that gangster movies simply wouldn’t be what they are today without it. Portraying society as entirely corrupt from top to bottom (provided you can spot the signs), while conveying that one’s culture, heritage, and family is almost impossible to escape, the film trilogy spawned by Puzo is nothing less than the definitive Italian-American tragedy.
Big themes, to be sure. But embodied wholly within the hopes, pains, and suffering of Michael Corleone (Al Pacino). The Godfather remains the quintessential film about any number of themes; gangsterism is just one of them.
That’s just 10 picks out of the entire genre of gangster and mafia movies, and the list of possible contenders was as full as it was award-winning. We could spend our time listing honorable mentions (Carlito’s Way, Casino, Mean Streets, City of God, King of New York) but will simply say that when a talented director and cast take on a gangster story, the results are usually worth watching.
Now that our list has ended, we ask you: which movies shaped your view of organized crime on celluloid? Was it the dirty 30s, or modern-day mobsters who pack the biggest punch?
We’ll see where Gangster Squad ranks when it hits theaters.
Follow Andrew on Twitter @andrew_dyce.