The Lawyer Who Fought to Free the First Woman Sentenced to Death in Chicago

Emilie Le Beau Lucchesi
Emilie Le Beau Lucchesi

In 1923, Italian immigrant Sabella Nitti became the first woman sentenced to hang in Chicago. There was no evidence she had committed the crime she was charged with, but prosecutors needed an easy win. Too many beautiful but guilty women had recently charmed their way into acquittals. In Sabella, prosecutors saw easy, ugly prey. She was haggard, poor, and unrefined. They swiftly convinced a jury that she had murdered her missing husband.

While Sabella waited to see if the high court would review her case, she was jailed with the scandalous women who inspired Roxy and Velma in the play Chicago. The musical version also had an innocent immigrant—the doomed Hungarian ballerina. A recent book, Ugly Prey: An Innocent Woman and the Death Sentence that Scandalized Jazz Age Chicago, is the first to tell the story of the woman who inspired the ballerina from the famed musical—and the young lawyer who rushed to pick up her case on appeal.

Helen Cirese waited for the elevators on the 11th floor. Her law firm, Bonelli, Quilici, & Cirese, was located in the City Hall Square Building on Clark Street in Chicago’s Loop. It was a brisk 10-minute walk to the Cook County Courthouse and Jail. Cirese crossed the Clark Street Bridge, glancing at the Chicago River below. At 23, she was a young and capable lawyer struggling to prove herself. Women did not serve on juries at the time, and the typical spot for a woman in the courtroom was in the gallery or on the witness stand. She found law firms unwelcoming to a young, female attorney.

Cirese had two strikes against her. She was female and she was beautiful. Her prospects for marrying a prominent man were immense. For traditionalists, it made no sense that Cirese was ignoring such opportunities in favor of a law career. But Cirese sensed what she could do and plowed ahead, regardless of the limitations other people set.

She surrounded herself with ambitious people and shared an office with several other Italian-American attorneys. They had talked about the murder trial dominating headlines. Sabella Nitti, a recent immigrant from Bari, was sentenced to hang for the murder of her missing husband.

The attorneys studied the newspaper stories. A few sat in on the trial. Sabella did not seem to be the cold-blooded killer the prosecutors described. She was a scared immigrant who spoke Barese, a distinct dialect of Italian that was difficult to translate. She didn’t understand what was happening to her in the courtroom.

What had happened was a miscarriage of justice. There was no evidence, no motive, and no positive identification on the decayed corpse found in a Berwyn drainage ditch. But prosecutors wanted an easy win. In the past few years, several beautiful but guilty women had charmed their way into acquittals.

Cirese dissected the discrimination she read about in Sabella’s trial. Was Sabella being sent to the gallows because she was guilty? Or because she was Italian? Or because Americans perceived her as ugly? Cirese wanted to know. Others in her office wanted answers, too. Five other Italian-American attorneys stepped forward, ready to join Cirese in defending Sabella on appeal.

It was a risk. If their efforts failed and Sabella swung, then Cirese and the other attorneys’ names would be attached to the failure. But what did Cirese have to lose? The men of the Chicago legal community didn’t accept her anyway.

Young attorney Helen CireseEmilie Le Beau Lucchesi

Cirese did not speak Barese. No one on the team of six spoke Barese. When Cirese stood outside Sabella’s cell in late July, Sabella saw a tall and slender woman smiling through the bars. Cirese saw a scared immigrant who didn’t understand why a jury wanted her dead.

Sabella was a compact woman with a muscular frame built during a lifetime of work. Her olive skin had deepened like tanned leather after years of toiling in the Mediterranean sun. She had long, thick black and gray hair that she piled onto her head in a messy bun and secured with pins and combs.

If Sabella had been born under different circumstances, it would have been easy to describe her as pretty. She had fine, arched eyebrows and round, close-set eyes. She had a slender nose, a wide mouth, and a defined jawline. In another life shaped by school or cotillion, a young Sabella might have charmed men by looking up at them with a wide smile and long, fluttering eyelashes. But a lifetime of desperation and work under the sun made her an easy target for newspaper reporters’ ridicule. Genevieve Forbes with the Chicago Daily Tribune called Sabella “grotesque.” She also described her as a “crouching animal” and “a monkey” for readers.

Cirese evaluated her client. Sabella’s arms were muscular from years of hard labor and she was painfully thin. To Americans, Sabella lay outside the standards of beauty. But Cirese saw Sabella’s potential.

Cirese brought a hairdresser to the jail and shared her vision for how to make Sabella beautiful. The hairdresser fussed with Sabella’s hair and then applied color to turn her graying strands into a deep, rich brown. She combed through Sabella’s long locks and picked up the scissors. Sabella needed a modern haircut in order to resemble a modern woman.

Cirese also made efforts to apply cosmetics to Sabella and clean her hardened hands. It was a transformation Sabella readily accepted. She was aware of how juries reacted to attractive women, and she knew American men did not find her good-looking.

The newspapers took note of Sabella’s makeover, and Cirese never hid her attempt to make her client more beautiful. Admitting her efforts was a smart move. It avoided any appearance that the defense was trying to be underhanded or manipulative. And it allowed critics to chastise the Cook County legal system for acquitting beautiful women while a homely but innocent woman was subjected to a trial so faulty that the Illinois Supreme Court had to intervene.

While the case waited among the backlog for the high court’s review, Cirese polished her client. Although the makeover efforts were never concealed, Cirese was far more discreet about her efforts to feed and fatten her client. Cirese never admitted as much, but she was Sabella’s most consistent visitor and advocate. It was likely Cirese who supplied Sabella with additional food items to supplement her sparse prison meals.

The makeover was one part of the plan. Cirese had other goals for helping Sabella appear more refined. Sabella’s English progressed during the winter and she was learning American mannerisms. Grunting, for example, was not becoming of a woman. Sabella was learning to keep in the sounds that made Americans cringe but felt so natural to her. She was also advised to refrain from the rocking she had a tendency to do when she was nervous.

The papers made mention of the “jail school” and the Chicago Daily Tribune’s Genevieve Forbes commented on how “jail can do a lot for a woman.” The comment was directed toward not only Sabella but the other women who were beginning to doll up before the court and ask for access to the cosmetics cabinet.

The makeup cabinet was about to see plenty of use. A new cohort of lady killers was headed to Cook County jail, each one determined to woo the all-male juries with their femininity.

Emilie Le Beau Lucchesi

By mid-April, the weather in Chicago had softened. Cirese strode across the Clark Street Bridge, headed to Cook County Jail with good news. The Illinois Supreme Court had ordered a new trial. Sabella would not hang. She would face a new judge and jury and have her case represented—this time by a competent defense team. Cirese delivered the good news to her client, and two weeks later, Sabella was ready for her first hearing.

The court had a full schedule. Two new lady killers had been recently arrested for shooting their secret boyfriends. Socialite Belva Gardner was the first in front of the judge. Belva shot her married boyfriend as he sat in her car. She claimed she was too drunk at the time to remember anything. She sat bundled in both a jacket and a wrap and wore a hat that slid low past her ears. She was quiet and reserved, and wore a pained expression. The full process had been quite irritating to her.

The newspapers took full note of what the fashionable socialite wore in court. Her attorney announced he was not ready to proceed and a continuance was ordered. The next case on the docket was called up. Beulah Annan, "Chicago’s prettiest slayer," was charged with shooting her secret boyfriend while her husband was at work. The redheaded beauty had confessed to the shooting, but later tried to change her story with reporters. Her attorney also wasn’t ready to proceed and a new date was scheduled for the following week.

Sabella Nitti was next and the prosecutor came to attention, noting the new woman sitting at the defense table by her pack of attorneys. The prosecutor looked across the room at Sabella. She wore a stylish black dress and high heels. Her hair was freshly colored, curled, and tucked under a light gray hat. She had a stack of papers in front of her and held a pen in her right hand. She looked as though she belonged at a ladies’ luncheon or country club event. Her entire demeanor had changed. Sabella sat quietly, folded into herself. She seemed optimistic about her day in court and had broken into a smile that spread cheerfully across her face. That was a terrible problem for the state—Sabella Nitti seemed sweet.

The prosecutor knew Helen Cirese was fixing her up—everyone knew it. Cirese wasn’t hiding her clean-up effort from anyone. In fact, she seemed to be using it against the state’s attorney’s office to insinuate that pretty women were rarely charged with murder, and that the lawmen were deeply biased. It was a disaster for the prosecution.

The state’s attorney’s office had the option to agree to dismiss the charges. But a dismissal would feel like an admission of wrongdoing. A new trial was set for the next month. Someone in Cook County needed to pay for their crimes, and Sabella was ugly prey the attorneys could target. They weren’t giving up. She'd see them in court.

Chicago Review Press

10 Killer Gifts for True Crime Fans

Ulysses Press/Little A
Ulysses Press/Little A

This article contains affiliate links to products selected by our editors. Mental Floss may receive a commission for purchases made through these links.

Humans have a strange and lasting fascination with the dark and macabre. We’re hooked on stories about crime and murder, and if you know one of those obsessives who eagerly binges every true crime documentary and podcast that crosses their path, you’re in luck—we’ve compiled a list of gifts that will appeal to any murder mystery lover.

1. Donner Dinner Party: A Rowdy Game of Frontier Cannibalism!; $15

Chronicle Books/Amazon

The infamous story of the Donner party gets a new twist in this social deduction party game that challenges players to survive and eliminate the cannibals hiding within their group of friends. It’s “lots of fun accusing your friends of eating human flesh and poisoning your food,” one reviewer says.

Buy it: Amazon

2. A Year of True Crime Page-a-Day Calendar; $16

Workman Calendars/Amazon

With this page-a-day calendar, every morning is an opportunity to build your loved one's true crime chops. Feed their morbid curiosity by reading about unsolved cases and horrifying killers while testing their knowledge with the occasional quizzes sprinkled throughout the 313-page calendar (weekends are combined onto one page).

Buy it: Amazon

3. Bloody America: The Serial Killers Coloring Book; $10

Kolme Korkeudet Oy/Amazon

Some people use coloring books to relax, while others use them to dive into the grisly murders of American serial killers. Just make sure to also gift some red colored pencils before you wrap this up for your bestie.

Buy it: Amazon

4. The Serial Killer Cookbook: True Crime Trivia and Disturbingly Delicious Last Meals from Death Row's Most Infamous Killers and Murderers; $15

Ulysses Press/Amazon

This macabre cookbook contains recipes for the last meals of some of the world’s most famous serial killers, including Ted Bundy, Aileen Wuornos, and John Wayne Gacy. This cookbook covers everything from breakfast (seared steak with eggs and toast, courtesy of Ted Bundy) to dessert (chocolate cake, the last request of Bobby Wayne Woods). Each recipe includes a short description of the killer who requested the meal.

Buy it: Amazon

5. Ripped from the Headlines!: The Shocking True Stories Behind the Movies’ Most Memorable Crimes; $15

Little A/Amazon

In this book, true crime historian Harold Schechter sorts out the truth and fiction that inspired some of Hollywood’s best-known murder movies—including Psycho (1960), Scream (1996), Arsenic and Old Lace (1944), and The Hills Have Eyes (1977). As Schechter makes clear, sometimes reality is even a little more sick and twisted than the movies show.

Buy it: Amazon

6. The Deadbolt Mystery Society Monthly Box; $22/month

CrateJoy

Give the murder mystery lover in your life the opportunity to solve a brand-new case every single month. Each box includes the documents and files for a standalone mystery story that can be solved alone or with up to three friends. To crack the case, you’ll also need a laptop, tablet, or smartphone connected to the internet—each mystery includes interactive content that requires scanning QR codes or watching videos.

Buy it: Cratejoy

7. In Cold Blood; $10

Vintage/Amazon

Truman Capote’s 1965 classic about the murder of a Kansas family is considered by many to be the first true-crime nonfiction novel ever published. Capote’s book—still compulsively readable despite being written more than 50 years ago—follows the mysterious case from beginning to end, helping readers understand the perspectives of the victims, investigators, and suspects in equal time.

Buy it: Amazon

8. Stay Sexy & Don’t Get Murdered: The Definitive How-To Guide; $13

Forge Books/Amazon

Any avid true crime fan has at least heard of My Favorite Murder, the popular podcast that premiered in 2016. This book is a combination of practical wisdom, true crime tales, and personal stories from the podcast’s comedic hosts. Reviewers say it’s “poignant” and “worth every penny.”

Buy it: Amazon

9. I Like to Party Mug; $12

LookHUMAN/Amazon

This cheeky coffee mug says it all. Plus, it’s both dishwasher- and microwave-safe, making it a sturdy gift for the true crime lover in your life.

Buy it: Amazon

10. Latent Fingerprint Kit; $60

Crime Scene Store/Amazon

Try your hand (get it?!) at being an amateur detective with this kit that lets you collect fingerprints left on most surfaces. It may not be glamorous, but it could help you solve the mystery of who put that practically empty carton back in the refrigerator when it barely contained enough milk for a cup of coffee.

Buy it: Amazon

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20 Best Gangster Movies of All Time

Viggo Mortensen in David Cronenberg's Eastern Promises (2007).
Viggo Mortensen in David Cronenberg's Eastern Promises (2007).
Universal Pictures Home Entertainment

Since the earliest days of cinema, gangsters have been the characters we’ve both loved and loved to hate. During the era of the Production Code, the heyday of the “gangster film,” Hollywood ensured that they were always brought to justice. But the popularity of their stories almost always owed more to the criminal exploits that led up to that moral reckoning, long after they’d won audiences’ admiration, envy, or even love. Their role was playing society’s outlaw, and their responsibility was to clash with its values to accomplish their own nefarious goals. That journey has endlessly fascinated viewers as a vicarious thrill, an escapist fantasy, or a truly primitive tale of good and evil.

When the Code lost its authority over film productions and stories about gangsters proliferated across the globe, portraits of their behavior, both good and bad, took on even more complex, ambiguous dimensions. Where once they were gleefully flaunting society’s rules, some gangsters sought legitimate paths—only to discover that their opportunities for success demanded that they cut a few corners or make deals with unsavory types; and some unsavory types upheld a certain code of honor that their supposedly law-abiding counterparts seemed to be challenging.

Making a list of the best gangster movies is tough, because there are lots of movies that overlap with this category without quite hitting the target. There are dozens of incredible heist movies, for example, and many others that study the criminal mindset without quite qualifying their characters as “gangsters.” But the films below explore the gangster as both a character and an idea at its fullest, most vivid, and most resounding. These 20 films are proof that crime pays off handsomely onscreen—even if we wouldn’t necessarily want to follow in their footsteps.

1. Public Enemy (1931)

Based on Beer and Blood, an unpublished novel written by two former newspapermen, William A. Wellman’s pre-Code gangster film gave James Cagney the role that would define his career. The story of a young gangster’s rise during Prohibition, Wellman’s film drew inspiration from real-life individuals and true stories from the heyday of Al Capone’s rivalries in Chicago.

Wellman cemented Cagney’s stardom after swapping his and co-star Edward Woods’s roles, but subjected the young actor to a number of dangerous scenarios, including a real punch to the mouth and a set riddled with live ammunition. Meanwhile, Cagney’s feverish intensity paved the way for decades of gangster roles as bracing and unforgettable as the grapefruit that he iconically smashes in co-star Mae Clarke’s face.

2. White Heat (1949)

James Cagney became known for tough guy roles in the early days of Hollywood talkies, giving audiences someone whose criminal exploits they could cheer for—at least until the Production Code imposed strict guidelines to ensure no one wanted to emulate him in real life. In his comeback with Warner Bros., Cagney plays psychotic hoodlum Arthur "Cody" Jarrett, whose fixation with his mother leads him deeper and deeper into trouble. Cagney’s refrain from the film—“Made it, Ma! Top of the world!”—became an instant catchphrase that echoed throughout film history in other films like Ernest Dickerson’s Juice, thanks to the actor’s unforgettable appeal giving the doomed crook glory, even in a tragic death at the hands of the authorities.

3. Bonnie and Clyde (1967)

Characterized as a “rallying cry” announcing the New Hollywood era at a time already full of turbulent change, Arthur Penn’s chronicle of Bonnie Parker (Faye Dunaway) and Clyde Barrow (Warren Beatty) inches toward the more open portrayals of sex and violence that the Production Code prohibited, and this film’s enormous success enabled later on. Beatty and Dunaway are sexy and mesmerizing as the tragic duo, following a foolhardy dream of becoming bank robbers to escape the boredom of their poverty-stricken lives, bringing Clyde’s equally reckless brother (Gene Hackman), his disapproving wife (Estelle Parsons), and an impressionable kid along for their doomed ride. In a genre dominated by mythmaking, Penn’s film tells how these two outlaws wrote their own story.

4. Get Carter (1971)

British crime exploded in popularity in the late 1960s and ‘70s, and Michael Caine was often the face of its jazziest, most violent expressions. In this adaptation of a 1970 Ted Lewis novel, Caine plays Jack Carter, a London gangster who travels home to discover that his brother was murdered—and decides to take revenge. Working with director Mike Hodges (who later directed the exceptional Croupier with Clive Owen), Caine aimed to deliver a more hardened, gritty portrayal of criminal behavior than he had in previous films like the brisker, more fun The Italian Job, even drawing upon real-life acquaintances he had with underworld types. Meanwhile, Hodges’s use of local bystanders as extras and a cinematographer with previous experience in documentary film further demystifies and grounds the action in this frequently brutal, amoral tale.

5. The Godfather (1972)

Despite the Italian-American Civil Rights League’s insistence that any mention of mafia and cosa nostra be excised from Francis Ford Coppola's adaptation of Mario Puzo’s story about the fictional Corleone family, no film has become more synonymous with organized crime—and indeed, the mob—than this sweeping drama. Coppola cemented not only his own career but those of Al Pacino, John Cazale, and others with a complex portrait of a family hierarchy where some members eagerly join the “family business” and others struggle against it. An entire legacy of gangster-inspired filmmaking can be traced back to The Godfather, perhaps appropriately, as so much of it is about legacies inherited, defined, and forged—to say nothing of the fact that it features some of the most exceptional writing, acting, and directing in cinema history.

6. Battles Without Honor And Humanity (1973)

Technically, Battles Without Honor and Humanity is not just one film, but five shot by director Kinji Fukasaku in less than two years. It examines the evolution of warrior codes—from sword fights to gunfights—in a post-WWII Hiroshima. Inspired by a series of nonfiction magazine articles, Fukasaku aims not only for an artful interpretation of real events, but utilizes narration, newsreel data, and other techniques to give his storytelling a vivid sense of authenticity. Meanwhile, the series’ violent landscapes track much more than a single gangster’s journey through an unforgiving criminal community, embracing and exploring the hierarchies, the power plays, and the bodies left behind the in the wake of the Yakuza’s march toward dominance—and perhaps self-destruction—at all costs.

7. The Friends Of Eddie Coyle (1973)

So many gangster stories are about low-level hoods and their attempts to navigate their way up the chain of command—to outsmart or outshoot people literally gunning for their job, or their stash. This Peter Yates film follows the title character, an aging delivery truck driver (played by the great Robert Mitchum), as he attempts to satisfy his criminal bosses while avoiding a pending jail stretch that will almost certainly kill him. Heists, double-crosses, and arrests multiply as poor, increasingly drunk Eddie tries to negotiate with an ATF agent who expects him to work as an informer, without betraying the confidence of a local bar owner (Peter Boyle) who he doesn’t know has already betrayed him. With its slow and sad end for an old man hanging on to his last scraps of life, the film depicts a much less noble career in crime than some other examples, which at least offer glory before that precipitous fall.

8. The Godfather Part II (1974)

After examining the path of Italian-Americans and the immigrant experience in the early 1900s with The Godfather, Francis Ford Coppola complemented that crime saga with a story inseparable from the fabric of the country in its sequel, following Michael Corleone’s journey at the head of the Corleone family while chronicling his father Vito’s humble origins in the America. Parallel journeys charted by Pacino and Robert De Niro spotlight how intrinsically immigrant lives are woven into the fabric of the country, and many industries that seem “legit,” while Coppola wields his scalpel carving away the last remnants of Michael’s humanity that his father was able to preserve for himself, and had once tried to protect for his children.

9. The Long Good Friday (1980)

The idea of “going legit” is one that is regularly explored in gangster movies, but few do it more effectively than in this British film about Harry Shand (an electrifying Bob Hoskins) and his imploded aspirations to become a businessman. Capturing the energy of late 1970s London, and the many issues that dominated the social landscape of the era, director John Mackenzie shunts Harry first through an intriguing mystery—who committed the murders disrupting his world?—toward an explosive climax between him and no less than the IRA, with his relationship with the American mafia staking his bid for legitimacy hanging in the balance.

10. Once Upon a Time in America (1984)

Sergio Leone turned down the chance to direct The Godfather to focus on his own crime saga, which he delivered 12 years later as his final film. Different versions forced Once Upon a Time in America to find its audience years after its initial release, but the almost-four hour-long version brought its transcendent virtues vividly into focus. De Niro plays Noodles, a street kid who grows up to become a powerful gangster, only for his scruffy criminal origins to haunt him for the rest of his life—including keeping him from the life and love he desperately seeks. Ennio Morricone’s tack-piano score underlines the melancholy failure of a man left penniless and alone by the same criminal pursuits that helped lift him out of squalor, while Leone’s patience offers a character study that in one operatic swoop encapsulates the achievement of lifelong dreams—and for some, their inescapable cost.

11. The Untouchables (1987)

Working in a different mode than his cocaine-fueled Scarface, Brian De Palma focused this period thriller on the good guys rather than the bad ones, but gave them perhaps one of the most infamous real-life gangsters of all time to square off against: Al Capone, played with simmering menace by Robert De Niro. The director’s homages to classic cinema, such as in the Battleship Potemkin-riffing train station shootout, showcase his effortless craftsmanship. But it’s the battle of wills between Capone, his ruthless henchmen, and Eliot Ness’s upstanding, fearless police unit that gives this film such a lasting charge.

12. Goodfellas (1990)

Where Coppola’s Godfather films—up to and including Part III in 1990—tried to examine the criminality of the Corleone family from a historical and socioeconomic perspective interlaced with the origins of America itself, Martin Scorsese’s mob masterpiece trekked through the invigorating minutiae of a young lieutenant and his hard-stolen success in a world that didn’t recognize his brand of overachieving, which is also why it couldn’t stop him sooner. Ray Liotta’s portrayal of mobster (and perhaps, inevitably, informant) Henry Hill jolts through the details of his life of crime, from the wild affluence to the peaks and valleys of living outside the law, while Scorsese’s propulsive direction draws a powerful question mark about whether it’s worse to be a criminal, or just to get caught—and what each viewer’s answer says about them.

13. King of New York (1990)

Few directors capture the seedy side of New York better than Martin Scorsese, but Abel Ferrara is right up there. In his 1990 crime story, Christopher Walken plays Frank Black, a crime lord recently released from prison who gets in a big hurry to make up for lost time, killing his competitors with ruthless efficiency while frustrating the cops who can’t seem to catch him. A murderer’s row of actors poised for their own stardom fill out its ensemble cast, but it’s Walken’s invigorating unpredictability that elevates his portrayal to classic status, balancing irresistible charisma with an ice-cold sociopathy that leaves audiences on the edge—afraid but also eager to watch his next move.

14. Miller’s Crossing (1990)

In their infinite capacity to recreate an anachronistic time and place with such specificity that you feel like you’re there, Joel and Ethan Coen told this particular story early in their career, a featherweight noir about a gangster’s right-hand man (Gabriel Byrne) and the trouble in which he finds himself after his boss (Albert Finney) and another rival (Jon Polito) go to war over the ne'er-do-well brother (John Turturro) of his sometime lady friend (Marcia Gay Harden). Effortlessly smart, and crackling with the kind of period jargon for which the duo is known, the Coens manage to showcase their protagonist’s endless, inventive maneuvering in a world of shifting loyalties, suggesting that it’s always possible to find another way out—although there’s almost always a punishing beatdown standing in the way.

15. Carlito’s Way (1993)

The Brian De Palma-Al Pacino pairing of Scarface is by far the showier, more popular option most might choose on a list of gangster films. But for many viewers, this 1993 effort written by David Koepp is the superior film, in that it keeps Pacino on a tighter leash playing gangster cues in a more minor, albeit more deeply felt, key. As Carlito’s increasingly corrupt attorney Dave Kleinfeld, Sean Penn enjoys the film’s biggest opportunity to chew scenery, but even if the film culminates in a blood-soaked race to Penn Station, Pacino’s turn gives the story a melancholy, reflective edge that makes you want to see him succeed with his modest, post-criminal dreams, even if the legacy he created for himself, and the associations and loyalties he maintains and even enables, prove to be an albatross he just can’t quite remove from around his neck.

16. Sexy Beast (2000)

Music video director Jonathan Glazer made his feature debut with this hypnotic story of a retired gangster (Ray Winstone) enlisted by his decidedly insistent former colleague Don (Ben Kingsley) to stage a robbery at the behest of mob boss Teddy Bass (Ian McShane). Winstone’s understated role as the reluctant bag man opposite Kingsley gives his co-star ample time to destroy the scenery and anything else in his way, but it’s McShane in the Big Bad role of Teddy that underscores the difference between a friend and a boss: You might be afraid to say no to the former, but when it comes to the latter, you’d better just start with yes.

17. City of God (2002)

Fernando Meirelles directed this sprawling, propulsive drama about the evolution of gangsters within Brazil’s slums between the 1960s and 1980s, and the growth of organized crime. It follows the city’s petty thieves, a.k.a. “The Runts,” as they evade police and accrue the wealth and status that a life of abject poverty refused them an opportunity to earn. Meirelles chronicles the ways that their consolidation of power is met with opposition from both the local, often equally corrupt authorities, and inspires copycats eager to carve out their slice of a very small pie.

18. Infernal Affairs (2002)

Andrew Lau and Alan Mak directed this film that became the inspiration for Martin Scorsese’s first Oscar-winning directorial effort, The Departed. The notion of cops and crooks being opposite sides of the same coin is an idea that has long been explored in cinema, particularly in Hong Kong, but Infernal Affairs gives the contrast explicit dimensions when a cop is sent to infiltrate a Triad at the same time that a low-level Triad member is instructed to become a mole in the police force. The movie reckons brilliantly with the emotional challenges of each of these two characters' undercover work, while shuffling them through scenarios meant to test their ability to maintain their true loyalties, to appear to be faithful to organizations they’re betraying, and to help catch their counterpart while not getting caught themselves.

19. Eastern Promises (2007)

After David Cronenberg more or less incidentally made a gangster movie, a masterpiece in its own right, with A History of Violence—arguably more about traditions of violence and what they imprint on families—he followed up with this piercing, full-throated story of a Russian mob enforcer (Viggo Mortensen) trying to juggle his responsibilities babysitting his best friend and boss’s petulant son Kiril (Vincent Cassel) while also dealing with the death of a young prostitute whose child leads back to a ring of kidnappings by the mafia. Mortensen’s buck-naked knife fight in a bath house is certainly the film’s showstopper, but Cronenberg explores the ties that bind, and some that shackle, while delivering a very powerful and evocative study of these characters shaped by privilege and then tested by responsibility.

20. A Prophet (2009)

Director Jacques Audiard created this story to give images “for people who don’t have images in movies, like the Arabs in France.” Whether it’s a good or bad thing that those images are of people ensconced in criminality, Audiard delivered something extremely powerful, following an angry, naïve young convict named Malik (Tahar Rahim) as he becomes part of an organized crime organization while behind bars. Slowly watching and learning as he ascends the ranks beneath his brutal Corsican mob boss, Malik becomes a proxy for the failed, forgotten and seemingly weak who decide to make something of themselves out of sheer determination and will—and sometimes almost without realizing it.