The 11 Charismatic Criminals Who Define Martin Scorsese’s Best Movies

Bill the Butcher (Daniel Day-Lewis) doesn’t walk into a room—he invades it, his presence as sharp as the cleaver on his belt. He doesn’t just dominate the world of Gangs of New York—he owns it, bending it to his will with a mix of brutal violence and theatrical flair. And similarly, Daniel Day-Lewis doesn’t just play Bill; he embodies him, swaggering through the Five Points like a king surveying his kingdom, every word dripping with menace and poetry. His speech about the “nature of the wound” is chillingly poetic, revealing him as a man who sees himself as a sculptor of history, shaping New York with blood and steel. The way he taunts Amsterdam (Leonardo DiCaprio) at the dinner table, hammering a knife into his own eye socket without flinching, is pure, terrifying showmanship—a performance within a performance. Bill is terrifying not just because he’s a butcher by trade, but because he makes violence feel like destiny. He commands respect not through fear alone, but through presence, through sheer force of personality, making even his most monstrous acts feel like law.

Bertha Thompson (Barbara Hershey) is one of Scorsese’s most charismatic criminals because she turns rebellion into an art form—she’s not just running from the law, she’s dancing through it. Hershey plays her with a devil-may-care charm, flashing a wide, defiant grin even as she drifts from con to con, from lover to lover, from train car to train car. Unlike the cold calculation of Casino’s Ace Rothstein or the ruthless ambition of Goodfellas’ Henry Hill, Bertha’s charisma isn’t built on control—it’s built on freedom. She seduces men with the same effortless ease with which she robs them, and when she pulls off a heist, it’s not about power, but play. Even when the stakes get deadly, like when she and her crew ambush a railway boss, there’s a magnetic recklessness to her—she believes in the cause but loves the chaos. And that’s what makes her unforgettable—she’s not just a criminal, she’s an outlaw in the purest sense, laughing in the face of a world that tells her to stay in her place.

Andrew Laeddis is one of Scorsese’s most charismatic criminals because he doesn’t act like one—he sells himself as the hero of his own story, and DiCaprio makes us believe him. Unlike the swaggering mobsters of Goodfellas or Casino, who revel in their power, or the scheming hustlers of The Wolf of Wall Street, who charm their way to fortune, Laeddis’s charisma is built on conviction, not confidence. He strides through Shutter Island with the intensity of a detective chasing justice, his voice clipped, his stare unwavering, his every move calculated to prove he’s in control. But the brilliance of his character—what makes him more magnetic than Scorsese’s gangsters and grifters—is that it’s all a performance, even to himself. The way he commands a room, challenges authority, and pieces together clues isn’t just gripping—it’s heartbreaking, because by the time the illusion shatters, we realize his greatest trick wasn’t fooling others, but convincing himself he was never a criminal at all.

Billy Costigan (Leonardo DiCaprio) walks into the bar of Frank Costello (Jack Nicholson) with a quiet, coiled energy, eyes scanning the room like he’s five moves ahead. He’s a man who can throw down in a bar fight one second and crack under the weight of his double life the next. DiCaprio gives him an electric unpredictability—whether it’s smashing a guy’s head with a glass to prove his worth or staring Costello down with barely concealed disgust, Billy is always teetering on the edge. Unlike the slick operators in Scorsese’s world, he’s not playing for power or money—he’s drowning in a role that’s eating him alive, and that raw desperation makes him the most tragic, yet captivating, criminal in Scorsese’s canon.

The first time we see Vincent Lauria (Tom Cruise) in The Color of Money, he’s grinning ear to ear, twirling his cue like a sword, and making impossible shots look easy—he’s got it all, and he knows it. No Scorsese criminal has been as effortlessly slick and frustratingly cocky, a pool hustler with Cruise’s megawatt charm and a dangerous addiction to showing off. Whether it’s humiliating seasoned players in Atlantic City or strutting around like a rock star, Vincent makes hustling look like performance art. But that same ego gets him hustled himself, blinds him to the lessons of old hat Eddie (Paul Newman), and nearly tanks his shot at true greatness. Scorsese doesn’t just make us admire Vincent—he makes us watch in frustration as his charisma and arrogance collide, proving that in his world, unchecked confidence is always the first step toward downfall.

Few cinematic criminals exude meticulous brilliance and effortless charm quite like Sam “Ace” Rothstein in Casino. Conveyed with clinical precision by Robert De Niro, Ace is not the kind of gangster who thrives on brute force or impulsive violence; instead, he is a meticulous strategist, a man whose power lies in his uncanny ability to read people and numbers alike. From the moment he steps into the Tangiers Casino, he commands absolute authority—not through fear, but through an almost hypnotic charisma. His early narration, detailing how he runs the casino floor with the efficiency of a Swiss watch, is as mesmerizing as it is insightful, revealing a man who treats gambling less as a vice and more as a science. Scenes like the one where he spots a dealer shuffling imperfectly and immediately fires him illustrate his near-superhuman attention to detail, making his presence feel omnipotent without him ever needing to raise his voice.

Yet despite his extraordinary competence, Ace’s charisma ultimately proves to be both his weapon and his Achilles’ heel. His ability to command respect unravels in the face of personal entanglements, particularly with the mercurial Ginger McKenna (Sharon Stone) and the reckless Nicky Santoro (Joe Pesci). His icy composure cracks in spectacular fashion when he pleads with Ginger in the restaurant scene, his desperation contrasting starkly with the unwavering control he exerts in the casino. Similarly, his growing paranoia—exemplified in the scene where he dons oversized pink-lensed glasses and wages a personal war against corrupt gaming regulators—signals the beginning of his downfall. In the end, Scorsese constructs Ace as a figure who redefines the archetype of the cinematic gangster, proving that in a world of unchecked ambition, even the most composed tactician can become a victim of his own allure.

Travis Bickle (Robert DeNiro) in Taxi Driver isn’t just an outsider—he’s a ticking time bomb wrapped in quiet, awkward charm. At first, he blends into the background of New York’s sleepless underworld, a loner who navigates the neon-lit streets with an almost ghostly presence. But beneath his detached exterior is an energy that draws people in, whether it’s his strangely endearing nervousness while asking Betsy out for coffee or his hypnotic conviction as he monologues about cleaning up the city’s filth. Even in his most unnerving moments—like the legendary one of him staring into a mirror, pulling an imaginary gun, and asking, “You talkin’ to me?”—there’s something undeniably magnetic about him. He doesn’t just play at being dangerous; he carries the weight of someone who genuinely believes he’s been chosen for a righteous mission.

Ultimately, it’s Travis’s warped sense of heroism that both elevates and dooms him. He transforms himself into a vigilante with a feverish devotion, shaving his head into a menacing mohawk and marching, gun in hand, toward a bloodbath he sees as salvation. The climax—his brutal, chaotic shootout to “rescue” Iris—cements him as an urban legend, a criminal who is mistaken for a martyr. Scorsese frames him not as a traditional villain but as a man so convinced of his own purpose that reality bends around him. He isn’t larger than life like Costello or Henry Hill; he’s something eerier—a man who thrives in the shadows, fueled by isolation, yet unable to resist the pull of infamy.

Robert De Niro’s Jake LaMotta in Raging Bull isn’t just a boxer—he’s a criminal in spirit, a man whose violence and paranoia make him as dangerous outside the ring as he is inside it. His world is built on domination, whether he’s throwing fights for the Mafia or terrorizing his own family with accusations and fists. His arrogance makes him believe he can outmaneuver the mob, yet he humiliates himself by taking a dive on their orders, absorbing each punch like a man who knows he’s already lost. But his worst crimes are personal—his jealous rages turn him against his wife and brother, his fists becoming weapons of control, not just competition. In a world where survival is about power, LaMotta’s downfall isn’t orchestrated by the Mafia but by his own inability to stop fighting, even when there’s no one left to hit but himself.

His self-destruction becomes literal when he is arrested for allowing an underage girl into his nightclub, his reckless arrogance catching up to him at last. By the time he sits in a jail cell, pounding his fists against the walls, sobbing “I’m not an animal!” the transformation is complete—he has become his own worst enemy, caged by the very violence that once made him great. Unlike the gangsters of Goodfellas or Casino, LaMotta’s crimes aren’t about power or greed but about a man who only knows how to destroy. Scorsese doesn’t just show his downfall; he shows a man who never knew how to stop swinging, even when the fight was long over.

Portrayed with gleeful menace by Jack Nicholson, Frank Costello in The Departed isn’t just a mob boss—he’s an almost mythical figure who moves through Boston’s underworld like a god who relishes in his own chaos. Right from his ominous opening monologue where he snarls, “I don’t want to be a product of my environment, I want my environment to be a product of me,” Costello asserts himself as the ultimate manipulator with the charm to make anyone believe him. He doesn’t just demand respect—he seduces loyalty and corrupts innocence with the charm of a devil wearing a velvet glove.

Eventually, the very untouchability that made Costello feel larger than life becomes the thing that seals his fate. He is so convinced of his own power that he underestimates the very machine he helped build, never once believing that Sullivan, his own hand-groomed mole, might turn on him. His brash arrogance peaks when he finally confronts Sullivan in a darkened warehouse, grinning like a lunatic as he cryptically asks, “Do you think they’d give you up?”—as if daring the inevitable. But the old-school gangster is already outdated, his unchecked reign of terror no match for a world where survival demands subtlety. He dies as theatrically as he lived, gunned down in a brutal execution, spitting blood and insults to the bitter end. Scorsese paints him as a man who thrived on dominance and manipulation, but like every titan of crime, he inevitably flew too close to the sun, mistaking fear for invincibility.

From the moment Ray Liotta’s Henry Hill breaks the fourth wall and delivers the iconic line, “As far back as I can remember, I always wanted to be a gangster,” Scorsese lets us know we’re in for a ride with a character as magnetic as he is morally bankrupt. Whether he’s taking his future wife Karen (Lorraine Bracco) on an effortless, one-shot stroll through the Copacabana kitchen entrance or flashing that manic, cocaine-fueled grin while juggling side hustles, Henry radiates the kind of effortless cool that makes his lifestyle look intoxicatingly irresistible. Even his darkest acts—like laughing off a man getting shot in a bar by Tommy DeVito (Joe Pesci) or using his charm to deflect Karen’s growing suspicions—are laced with an undeniable charisma. Liotta brings a kinetic, boyish energy to Henry, making him both an aspirational and tragic figure, a guy who seems too slick to fail until, inevitably, he does.

And like all Scorsese antiheroes, the very qualities that made Henry larger than life are what send him crashing down. That confidence curdles into paranoia as he spirals into drug addiction, sweating through a single day of frantic coke deals while dodging the FBI helicopter that stalks him from above. His casual betrayal of his closest friends to save himself in the courtroom is less a grand Shakespearean downfall and more a pathetic whimper—Henry, once the smooth-talking wiseguy with the world at his fingertips, reduced to a schlubby suburban nobody forced to live like a “schnook.” Unlike Jordan Belfort, who lands on his feet with a new scam to run, Henry’s fate is less poetic and more tragic: a man who had it all, lost it all, and can never get it back. Scorsese doesn’t just tell us how alluring crime can be—he shows us, and then he shows us why it never lasts.

No Scorsese criminal has been simultaneously as irresistibly charismatic and as undeniably problematic as degenerate playboy and Wall Street trader Jordan Belfort in The Wolf of Wall Street. Besides casting Leonardo DiCaprio, one of the most charismatic movie stars of all time, to play Belfort, Scorsese seems dead set on making his criminal exploits as reprehensible and thrilling as possible. We all know driving under the influence is reckless and can kill innocent people. That didn’t stop any of us from nearly projectile vomiting from laughter watching Belfort crawl to his car to drive home under the influence of 15-year-old Quaaludes. There’s Belfort’s famous “I’m not leaving” speech that could hype up a corpse, Belfort casually explaining how his firm committed market manipulation through backdoor IPO deals, and of course, there’s Belfort’s sales psychology lesson on display in getting someone to sell him a pen.

Eventually, the same arrogance and charisma that Scorsese inundates us with is what begets Belfort’s fall. His feeling of being untouchable leads him to disregard FBI investigations which leads to him taking incriminating phone calls which leads to his arrest. He nearly dies when his yacht capsizes after he wanted to ride in a storm in order to smuggle money out of Switzerland. The man who was worshipped as a god by employees like Donnie Azoff (Jonah Hill) eventually turned on those people to save himself. In the end, Scorsese paints a cautionary tale of how charisma and criminality only mix for so long before the former makes the latter a kind of death sentence.