The Most Frightening Gangsters on Film


You’d be hard pressed to find a movie tough guy with a more diverse filmography than Bob Hoskins. The English actor passed away earlier this week. With a burly silhouette, an aura of cockney cool, and a glimmer of menace in his eyes, the versatile performer charmed audiences as a sympathetic everyman and heroic detective (Who Framed Roger Rabbit), but was startling as a vicious gangster in films like The Long Good Friday. The straight-talking star played a number of cinema toughies during his colorful career. In honor of Hoskins’ reign of terror, we revisited some of cinema’s most frightening film gangsters.

Lee Marvin as Walker in Point Blank

A quintessential movie tough guy, Lee Marvin lived the life he portrayed on the big screen. The towering, gravelly-voiced performer was a marine sniper during the Second World War and had the battle scars to prove it. Delivering an iconic performance in John Boorman’s revenge tale, Point Blank, Lee’s Walker goes on a vengeance-driven rampage after his wife (Angie Dickinson) and partner in crime (John Vernon) double cross him. Lee established he was capable of much of more than just playing the traditional tough guy parts, but he was damn good with a gun in his hand.

Gary Oldman as Norman Stansfield in Léon: The Professional

Oldman isn’t given an abundance of screen time in Léon, but his character’s lunatic presence can be felt in every scene. We’re slightly cheating here as Oldman’s Stansfield is an archetypal crooked cop, but the drug-addled DEA agent leads a double life as a criminal mastermind. Oldman brings the unforgettable character to the forefront with flamboyant speeches, wild physicality, and palpable insanity as he systematically murders his way through an entire family.

Ben Kingsley as Don Logan in Sexy Beast

Ben Kingsley is one of the greatest reasons to see Jonathan Glazer’s Sexy Beast, in which the actor’s brutal London gangster makes even the most vile criminals cringe. Kingsley’s Don Logan enlists the help of his former associate Gal (Ray Winstone) for a bank heist, shattering the retired safecracker’s now idyll world. Gal’s refusal only fuels Logan’s bitterness and fury, propelling the sociopathic figure into a fearsome meltdown. His outbursts are marked by rapid-fire, foul-mouthed rage, but Logan’s quiet sneer is equally bone-chilling.

Takeshi Kitano as Uehara in Boiling Point

Takeshi Kitano is a triple threat in the laconic yakuza crime tale Boiling Point, taking on the roles of director, actor, and writer in the 1990 film. Boiling Point marks Kitano’s beginning as an auteur, but it also featured the imposing talent as a ruthless gangster. Unpredictable and disaffected, Kitano’s Uehara carves his own path through criminal Japan with stark and startling results, painting the screen with bursts of violence.

Michael Madsen as Mr. Blonde in Reservoir Dogs

In Quentin Tarantino’s unapologetically violent debut film, Reservoir Dogs, paranoia sets in amongst a thieving ring of men after a botched jewel heist. Named after colors to obscure their identities, one of the most unhinged in the group, Mr. Blonde, tortures and kills for his own amusement. A longtime character actor to that point, Michael Madsen’s portrayal of the razor-wielding con caught the attention of critics, and the actor emerged as a force to be reckoned with.

Tadanobu Asano as Kakihara in Ichi the Killer

“There is no love in your violence,” sadomasochistic yakuza enforcer Kakihara (Tadanobu Asano) utters at an opponent. He speaks this line before tearing out his cringe-worthy facial piercings that seemingly hold his face together and shredding the man’s hand apart in his mouth. As Kakihara slaughters his way through the abyss of Japan’s criminal underworld to seek revenge for his boss’ death, he employs some… unorthodox methods to make men talk. He even turns the blade onto himself in jaw-dropping acts of violence, delighting in the pleasures of pain.

Dennis Hopper as Frank Booth in Blue Velvet

Dennis Hopper steals the spotlight in David Lynch’s ode to suburban malaise, Blue Velvet. The meeting of small-town innocence and unrepentant evil, portrayed through Kyle MacLachlan’s naive college student and Hopper’s depraved criminal, is as Lynchian as it gets. Hopper embodies the villainous role in an over-the-top performance — a flurry of rage, sadism, and drug-fueled terror.

Joe Pesci as Tommy DeVito in Goodfellas

Joe Pesci’s Oscar-winning turn as a deranged wise guy with a hair-trigger temper is richly deserved. With a lesser actor, the role might have been shrouded in mere foul-mouthed fits, but Pesci’s Tommy, who aids the rise of Lucchese crime family associate Henry Hill, is more complex than that. The thuggish fiend grapples with deep-seated insecurities and a paranoia that haunts. Tommy can shoot a young boy without flinching, but still make it home in time for dinner, reverting back to the stunted mama’s boy he really is.

Christopher Walken as Vincenzo Coccotti in True Romance

The top-notch supporting cast of Tony Scott’s True Romance vanishes quickly, many of the actors appearing in only a few scenes before they’re dispatched in typically Tarantino (read: gleefully violent) ways. The writer-director, who is on script duty for the 1993 film, gives some of the best moments to Christopher Walken, whose finesse as a single-minded crime boss is mesmerizing. The veteran actor is paired with another great, Dennis Hopper, for a memorable scene that culminates with a hysterical exchange of words before finally exploding in violence. Walken makes the most of the small part with a sly menace that chills.

Daniel Day-Lewis as Bill ‘The Butcher’ Cutting in Gangs of New York

A bare-knuckle bruiser with a penchant for tapping his glass eye with a knife, Daniel Day-Lewis cuts an imposing figure as Bill ‘The Butcher’ Cutting in Martin Scorsese’s Gangs of New York. His moustache-twirling antics and jaunty 19th-century garb make him a charming monster, but The Butcher is a manipulative, full-bore psychopath who stops at nothing to maintain his control of the Five Points neighborhood.