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The 22 Greatest Mob Bosses In TV & Film

The 22 Greatest Mob Bosses In TV & Film

This weekend, with the paint still wet from its Venice Film Festival premiere, you get to check out Scott Coopers “Black Mass” for yourselves (our review is here). The story of notorious Boston crime lord James “Whitey” Bulger (Johnny Depp), his rise to FBI-aided prominence as the city’s most feared gangster, his fall from grace after his associates turned on him, his decades-long subsequent reign on the FBI’s Most Wanted list, it’s part a genre we’re eternally fascinated with, whether based in truth or not. The fact is, mob movies exert a powerful influence over our cinematic imaginations because of the glimpse they show us of the dark side, the underbelly of polite society, and the codes that are practiced, and broken, there. Some “mobs” are little more than glorified street gangs, while others have reach and influence extending so far they’ve wormed their way into the very fabric of the societies they prey on, but they’re all characterized by tribalism and arcane ethical rules, and all orbit around the magnetic pull of the boss.

READ MORE: Venice Review: ‘Black Mass’ Starring Johnny Depp, Joel Edgerton, Benedict Cumberbatch, And More

With Depp’s interpretation of Bulger soon hitting screens, we thought it was time to take a look at his competition, new and old, on big screens and small, in the battle for who should be crowned King of the Kingpins, Lord of the Crime Lords, Donnest of the Dons. Bearing in mind that we tried to work to only one entry per film or TV show, here are our 22 favorite onscreen mob bosses.

Tony Soprano (James Gandolfini) in “The Sopranos”
New millennium dad. Unfaithful husband. Needy husband. Tough-ass mob boss. The many sides of Tony Soprano, New Jersey’s most-feared and insecure Mafioso, required a whole lot of time to cover  six groundbreaking seasons of television, in fact. And who better to embody this marauding, soft-voiced killer-bear of a man than James Gandolfini, who can do threatening machismo mixed with crippling self-doubt better than just about anyone? Over the course of “The Sopranos” hilarious, horrifying six-season run, Tony found himself at the mercy of two families: the one he started with Carmela, (the magnificent Edie Falco) his long-suffering wife, and the DiMeo crime family, a merciless pack of vipers who kill with the same ease that they order up a plate of ziti. Gandolfini’s work here is notable for being one of the most psychologically astute portraits of the modern male gangster ever filmed. Indeed, Tony is often more frightening when he’s sitting in his therapist’s office talking about his mother than when he’s beating the crap out of some helpless sap who owes him money. Talk about a real 21st century man.

Janine ‘Smurf’ Cody (Jacki Weaver) in “Animal Kingdom”
The fact that Jacki Weaver didn’t show up in Hollywood until 2012 is a bit of a crime in itself. Weaver had been knocking it out of the park for decades in her native Australia, so it’s no surprise that her international breakout would be in the form of the excellent “Animal Kingdom” from fellow Aussie David Michôd. Weaver plays Smurf, the matriarch of a family of armed robbers, a woman so loving and smooth on the surface that as the film unfolds, one of its finest pleasures is watching her gradually revealed as the vilest of them all. As her family and way of life crumble, death after death, one of the darkest hearts in recent cinematic history is unveiled. And Weaver does it all with such a tender surface, with such a soft voice, it’s impossible not to feel a shiver of dread as the film comes to its inevitable climax. Ultimately, the true power of Weaver’s performance can be surmised by the meager-by-comparison screen time she has and the ungodly number of awards and nominations that were, justifiably, thrown at her feet.   

Frank Costello (Jack Nicholson) in “The Departed”
Jack Nicholson’s beantown psycho from Martin Scorsese’s “The Departed” is a man of savage, insatiable tastes who’s as likely to push a prostitute face first into a mountain of coke as he is to wave around a severed hand just to make a point. Costello is also loosely based off James “Whitey” Bulger, but even if the star of “Black Mass” looks genuinely freaky with his colorless eyes and balding pate, it’d be hard for the Deppster to come within spitting distance of Nicholson’s work here, which goes so far over the top that it practically qualifies as performance art. Scorsese’s tale of rats and roaches in fearful, post-9/11 America has a mean undercurrent of mordant comedy, and some of Nicholson’s best scenes  like when he gives Matt Damon’s duplicitous mole a nasty surprise in a porno movie theatre  occur when the actor is allowed to let loose. In a film graced with gifted actors giving nuanced performances, Nicholson flies gloriously off the handle here, but he’s never anything less than a joy to watch.

Michael Corleone (Al Pacino) in “The Godfather Part II”
Although Al Pacino’s subsequent turns in “Scent of a Woman” and “Glengarry Glen Ross” gave him a reputation as a perpetual overactor, who can forget that he did such grand yet understated work in the 1970s for directors like Sidney Lumet (“Serpico” is an undeniable highlight) and, of course, in Francis Ford Coppola’s lush, funereal “Godfather” pictures. The second film in Coppola’s operatic saga of the Corleone family marks an interesting turning point: while his Michael Corleone was, at least on the surface, fundamentally good in the first film, something rotten seems to have taken over in ‘Part II,’ so here Pacino smolders with simmering resentment, without once letting histrionics take over. He’s all the more terrifying for what he doesn’t say, for what his face doesn’t even betray with a flicker. His depiction of Michael as a man who all-too-willingly assumes his father’s reins as a ruthless murderer is one of the actor’s finest accomplishments, as well as one of the most nuanced and intelligent depictions of a gangster slowly losing whatever morals he once had.

Li’l Ze (Leandro Firmino) in “City of God”
Fernando Meirelles and Katia Lund‘s “City of God” is electric cinema, but it’s also notable for being one of the most unsentimental portraits of the criminal life ever filmed. There is no sense that the gangsters in this film are anything other than stupid, desperate young men, blindsided by the need for mentorship and respect, and willing to resort to the basest means of human behavior to achieve what they seek. Nowhere is this more apparent than in the film’s portrait of Li’l Ze, a sadistic drug-pusher who takes a disturbing pleasure in watching his victims squirm under the gun. This fuck-the-world nihilism reaches its uncomfortable culmination in a deeply upsetting scene where Ze taunts a child who looks to be no older than seven before shooting him in the foot and forcing one of his lackeys to finish him off. It’s brutal stuff, but Ze’s nightmarish laugh sticks with you, even overriding the many other harrowing scenes in “City of God.” It’s a film, and a performance, that strips the gangster genre of any and all romantic notions, all while remaining stylish, intelligent, and raw.

Harold Shand (Bob Hoskins) in “The Long Good Friday”
John Mackenzie‘s terrific 1980 film, “The Long Good Friday,” remains the pinnacle of the British gangster film, and Hoskins, as Harold Shand, a London gangster wanting to go legit, remains the pinnacle of the British movie hoodlum (though Tom Hardy‘s not bad in the upcoming “Legend“). Shand, trying for one last huge score before going straight, has a property development scheme in place for London’s Docklands, in the hopes that it might serve as the site for a future Olympics. But he is stymied by an unknown enemy (probably the IRA), who causes the U.S. mafia to pull out of the agreement, leaving Shand high and dry and desperate to hold his crumbling empire together. It’s a film that sums up its era  timed to the arrival of Margaret Thatcher in government, Shand is the kind of figure who would have flourished under her. But political subtext aside, it’s also simply a gripping thriller, with a star-making performance from Hoskins (his final scene, as he’s confronted by an IRA hitman, Pierce Brosnan in his first screen role, is a masterclass) that shows both the peaceful, honorable man Shand wants to be, and the psychotic thug that lies underneath.

Marcellus Wallace (Ving Rhames) in “Pulp Fiction”
“Fuck Pride. Pride only hurts. It never helps.” So sayeth the feared Marsellus Wallace, the silky-voiced crime capo who acts as one of many moving parts in Quentin Tarantino’s profane, epochal “Pulp Fiction”. As Wallace, Rhames has an ingratiating smoothness that is decidedly at odds with the more blustering, macho energy that a lesser actor might have delivered in the role. Marsellus, in spite of clearly being in charge of some faction of a criminal empire, seems curiously nonplussed throughout most of Tarantino’s chatty, twist-filled narrative. It’s not until he finds himself at the mercy of two sadistic redneck thugs  we all remember that “Gimp” scene  that we get to see the beast unleashed. Rhames, ever the canny and intuitive performer, feels no need to overstate the man’s ruthlessness. It’s all implied, and doubly effective in that regard. Never have the words, “I’m gonna get medieval on your ass,” sounded so sexy, or so cool, or so goddamn threatening. Rhames is frequently overshadowed by the more popular and flashy work of co-stars John Travolta and Samuel L. Jackson, but he makes a memorable heavy in Tarantino’s most beloved picture.

Nucky Thompson (Steve Buscemi) in “Boardwalk Empire”
Twenty or so years ago, Steve Buscemi might have been tasked to play the knuckle-cracking, motor-mouthed henchmen to a mob moss. It’s doubtful that anyone would have had enough faith in the actor’s cachet to ask him to play a bonafide criminal kingpin. And yet, that’s exactly what Terence Winter did with his sprawling, problematic prohibition saga “Boardwalk Empire.” In the HBO series, Buscemi plays Enoch “Nucky” Thompson, who, like many a gangster before him, struggles to reconcile the legitimate elements of his business with his, shall we say, off-the-books habits. Winter’s show doesn’t get points for originality, and, too frequently, it falls back on mere macho bluster instead of finding new and inventive ways to push the narrative forward. But Buscemi’s brainy, subtle turn as a conflicted dealmaker during America’s most decadent decade frequently gives the material a big boost, even convincing us to give this slot to him, amongst so many other great hoodlum honchos in this show, from Stephen Graham‘s nascent Al Capone to Michael Stuhlbarg‘s genius cold-fish Arnold Rothstein. Buscemi defines the kind of gangster who’s more at home greasing the palms of business rivals than exacting brutality on his foes, yet still towers across this show.

Tony Montana (Al Pacino) in “Scarface”
It’s been argued that Al Pacino’s berserker turn as megalomaniacal cocaine cowboy Tony Montana in “Scarface”  a remake of a Paul Muni-starring film from 1932 that substituted cocaine for prohibition-era alcohol trafficking, as well as an unfortunately cannibalized staple of much mid-90’s gangster rap  is a notable example of chewing the scenery. While this claim is, on the surface of things, hard to deny, the point itself seems reductive when you consider how stupidly, unapologetically over-the-top Brian De Palma’s whopper-sized mobster saga truly is. Pacino’s hammy turn as a Cuban refugee who gets rich selling white stuff on the sandy shores of 1980s Miami is only as opulent and exaggerated as the film that surrounds it. Pacino’s is a performance that has spawned an inordinate number of catchphrases and remains a dizzying career high, especially for being the polar opposite to his restrained turn in “The Godfather Part II,” yet in broadly the same arena. It may not be your cup of tea, and it occasionally resembles a splashily-colored slasher movie  see the infamous chainsaw scene  but ask frat boys and rap stars around America, and Tony Montana is the bad guy you want to say goodnight to.

Leo O’Bannon (Albert Finney) in “Miller’s Crossing”
It’s a long way from the flamboyant Belgian detective Hercule Poirot to Leo O’Bannon, but Albert Finney spans that whole immense distance. As the polished Irish American mob boss, Finney handles every situation with the same finesse he would a clue upon the Orient Express, or a shot glass in “Under the Volcano”. In the Coen Brothers’ 1990 film, Finney is immersed in a detailed pastiche of the 1920s gangster flick and its Prohibition-era illicit watering holes, where he finds himself in a power struggle with his nemesis, Italian American mob boss, Johnny Caspar. Between the two bosses is O’Bannon’s right-hand man and general factotum, Tom (Gabriel Byrne), who is sleeping with O’Bannon’s girlfriend and colluding with Caspar. O’Bannon, who could really be a kind of predecessor to Don Corleone, must face the ethical complexities of friendship and loyalty, all while controlling dirty cops and trigger-happy enemies. A perfect execution of the Coen’s rat-a-tat dialogue and neo-noir comedy, Finney is of paramount importance to a great film that manages to somehow to be underrated in their canon.

Wilson Fisk (Vincent D’Onofrio) in “Daredevil”
Vincent D’Onofrio has been an underrated performer for longer than most millennials have been alive: funny to think there’s a generation that knows him best from “Law and Order.” The diversity of his roles has been impressive, but more often than not his solid work somehow blends into the film or is unjustly overshadowed by whichever handsome actor is playing the good guy (see this summer’s “Jurassic World”). “Daredevil” creator Drew Goddard had something else in mind though for his Marvel show. From episode one it’s clear that Wilson Fisk is as much the star as Matt Murdock. And damn, does D’Onofrio run with the character. Fisk, first and foremost, is a man; a human being full of passion and love and loneliness. But in D’Onofrio’s hands, Fisk is also a monster. A force of nature. He’s equally as compelling and complex as Murdock, though Fisk, shockingly, seems to get the more emotional role: his relationship with Toby Leonard Moore’s James Wesley is as powerful and deeply realized as anything else on TV this year. D’Onofrio is heartbreaking, magnetic, and almost too relatable for our own comfort.

Al Swearengen (Ian McShane) in “Deadwood”
In the fictional tale of the actual town of Deadwood, South Dakota, Ian McShane’s diabolical turn as Al Swearengen is simply one of the most memorable and ruthless villain/antihero roles in television history, because, as any fan of the show knows, despite Al’s meticulously cunning, murderous ways, he might be the most likeable guy in town. The owner of The Gem, Deadwood’s original brothel and whiskey joint, Al spends his days (and the majority of the show’s scenes) in his top-floor office or its adjacent balcony overlooking new developments (not to mention enjoying a bird’s-eye view of his enemies’ movements). Amidst the animal feces, frontiersman chatter, and rampant disease, Swearengen’s quick-wit and uncanny ability to solve (or create) problems are unmistakable, particularly in his encounters with Sheriff Seth Bullock. Swearengen and Bullock (the ever-intense Timothy Olyphant) are sometimes dramatic foils, sometimes confidants, sometimes throwing-each-other-over-a-balcony types, and it’s these brilliantly written encounters especially that make McShane’s terrific and domineering performance so memorable.

Vincenzo Coccotti (Christopher Walken) in “True Romance”
Though the character of Vincenzo Coccotti is only in the film for a few minutes, Christopher Walken’s turn as the Sicilian counsel for Blue Lou Boyle, and his exchange with Dennis Hopper as Clifford Worley, is unquestionably one of the great scenes in mobster cinema. Clifford Worley’s newlywed son, Clarence (Christian Slater), has just taken off, and right on his tail are Coccotti and his meaty cohorts, looking for stolen cocaine, Clarence, and his beautiful bride Alabama. In a quotable altercation, Coccotti explains coyly to Worley that he is in fact the antichrist, just before knocking him in the nose — the beginning of Worley’s torture. Indignantly, Worley shoots back a few ignonimous one-liners about Coccotti’s Sicilian heritage, but it’s no matter — after smoking a Chesterfield and calling him a cantaloupe, Coccotti blows Worley away, killing someone for the first time since 1984. Only Quentin Tarantino could write such a bewitchingly bloody scene, and in one short burst, give us the Walken role we’ve always, always wanted to see him play.

Al Capone (Robert De Niro) in “The Untouchables”
Identified more than anyone since Robinson and Cagney with the mobster, Robert De Niro has more often than not played a criminal on the way up who ends up (sometimes just temporarily) running the show — see “Godfather Part II,” “Goodfellas,” “Once Upon A Time In America,” et al. But perhaps his purest mob boss turn, the most in-command and fearsome, if by no means the biggest, is his Al Capone in “The Untouchables.” Brian De Palma’s remorselessly entertaining reboot of the TV series neatly straddles the line between comic-book and realism, and never more so than with De Niro’s depiction of the legendary mob boss. There have been plenty of screen Capones, and to some degree what the star does here isn’t that different from some of his other gangster gigs, but it’s his decision to play Capone as a consummate politician, charming the press and rousing his colleagues before switching on a dime and showing the monstrous violence inside him, that sets it apart. It’s a performance so good that it’s a little disappointing that the baseball-loving bastard lurks in the shadows for most of the movie.

Rico (Edward G Robinson) in “Little Caesar”
Edward G. Robinson might have looked a little like the suavest baby you ever saw, but as “Little Caesar,” his big breakout starring role made clear, he could be entirely fearsome too. Mervyn LeRoy’s 1931 gangster classic sees Robinson’s Rico as a hood on the make in Chicago, soon controlling the whole of the Northside, with Douglas Fairbanks as his old pal Joe, who just wants to dance (!), but whom Rico won’t let out of the criminal life.  One of the earliest crime talkies, it proved influential not just on Robinson’s career (he was typecast in similar roles for years to come), but on the genre as a whole — so many mobsters afterwards owe a debt to Robinson’s snarl and distinctive speech patterns. As far as the film itself goes, everything with Fairbanks is kind of a wash, but the movie sings every time Robinson’s on screen, not least in his iconic final moments — “Mother of mercy, is this the end of Rico?” In the film it certainly is, but his legacy lives on long after.

Yoshio Yamamori (Nobuo Kaneko) in “Battles Without Honor And Humanity”
Widely interpreted as influenced by “The Godfather” (which only came out the year before) Kinji Fukasaku‘s “Battles Without Honor And Humanity” (also one of the greatest bombastic titles of all time) is known today as the first “modern” Yakuza picture. Prior to ‘Battles,’ which went on to spawn four sequels in just the next two years, Japanese cinema tended to portray the Yakuza as adhering to fundamentally honorable Samurai-influenced codes of conduct. But Yamamori (Nobuo Kaneko), head of the clan that the film’s hero, Hirono (Bunta Sugawara), joins only to find that loyalty is worthless and betrayal is a way of life, is an unusual kingpin, neither slick nor cool, just a consummate, desperate hypocrite, who has stayed on top by simply being a bigger rat than everyone else. The first sequence in ‘Battles’ depicts the Hiroshima A-bomb; Yamamori represents the embodiment of dishonor and weaselly self-interest because in his violent, garish film (a major influence on Tarantino), Fukasaku suggests that Japan’s honor and humanity were also pulverized in that explosion.

Stringer Bell (Idris Elba)/Marlo Stanfield (Jamie Hector) in “The Wire”
While David Simon’s “The Wire” is ultimately too anthropological to qualify as solely a crime serial, the show’s unflinching depiction of the poverty and drug traffic that plagues Baltimore’s worst neighborhoods still stings after all these years. Two soldiers on Baltimore’s urban battlefield gave Simon’s show both its dark soul and also its rotten, reptilian underside in the form of Stringer Bell (Idris Elba) and Marlo Stanfield (Jamie Hector). Since the characters hail from different eras of the show’s five-season run, we’re bending our own rules and including both. Elba plays Stringer as a pragmatic hardhead, a drug kingpin with political ambitions who is essential in the ascent of the Barksdale drug organization that dominates seasons 1-3. He’s a man who yearns to legitimize his fundamentally illegitimate business, and he’s also, ultimately, hopelessly naïve about what said business entails. Stanfield, meanwhile, is a snake: heartless and without a single ounce of human feeling. You look into his eyes and see nothing but the blind, unquestioning demand for profit, respect, and the begetting of more and more ruthless violence. As twin portraits of very different kinds of gangsters, Elba and Hector have very different styles, but they’re respectively electrifying.

Frank Lucas (Denzel Washington) in “American Gangster”
Until “The Martian” at least, Ridley Scott’s best film of his post-“Gladiator” period was likely “American Gangster.” It’s a little stodgy, sure, but this biopic of Frank Lucas, one of the biggest heroin traffickers in U.S. history, penned by Steve Zaillian, is consistently involving and engrossing, even if it doesn’t quite manage to reach greatness. Russell Crowe arguably has the showier role, as the cop trying to bring Lucas down, but it’s Denzel Washington who dominates the movie as Lucas. This wasn’t exactly new ground for the star, but he’s a measure of absolute control in the movie, a businessman first and foremost. Most of the mobsters on this list are driven to violence when they lose their cool, but Lucas’s violent acts (killing a rival, played by Idris Elba, in broad daylight) are as considered and meticulous as anything else he does, and that makes him even more terrifying. Even then, though, Washington doesn’t make him a monster — he’s a man desperate to be accepted by an establishment that’ll never have him, an interesting take on the archetype that pays off satisfyingly.

Vee (Lorraine Toussaint) in “Orange Is The New Black”
The second season of Netflix and Jenji Kohan’s terrific prison drama, “Orange Is The New Black,” which arrived last year, got a huge boost with the arrival of a new antagonist, Vee, played by Lorraine Toussaint, who’d come hot off a scorching turn in Ava DuVernay’s “Middle Of Nowhere.” Vee is a long-time Litchfield inmate who’s been out for a while, having returned to her drug business only to get busted again. An expert Machiavelli-level manipulator, Vee’s a force of nature, strong and seductive, and not even remotely to be trifled with, as many inmates, most notably Red, find out. And yet Toussaint, wily like a fox and fearsome like a bear, also plays her from the beginning like someone who knows she can’t stay ahead of the game for much longer, and the increasing desperation as time goes on makes her both more dangerous and more tragic. It’s a classic mobster arc, but it rarely been played better than it is here by Toussaint.

Cody Jarrett (James Cagney) in “White Heat”
What Edward G. Robinson did the mobster in the 1930s  i.e. defined it for the public at large  Jimmy Cagney did for the post-war era with Raoul Walsh’s cracking noir, “White Heat.” Like Robinson, Cagney was baby-faced even at fifty, giving his criminal, Cody Jarrett, who tries to keep control of his gang after doing time for a mail-train robbery, the feel of an overgrown, misbehaving child, helped no end by his frankly disturbing attachment to his Ma (Margaret Wycherly). More than most, Cagney’s Cody looks born to the outlaw life, positively revelling in his psychopathy, up to and including the moment of his explosive demise, as he famously screams, “Top of the world, Ma!” To say that Cody (who was based in part on real-life criminal Francis Crowley) is involved in organized crime is perhaps to overstate the case: he flies by the seat of his pants to a degree, an impulsive, spontaneous figure, and is doubly dangerous for it. It means that, even as you’re afraid of him, you still can’t help but root for him a little.

Malik El Djebana (Tahar Rahim) in “A Prophet”
It’s a familiar arc — common criminal climbs inch-by-inch to the top of the tree — but it’s rarely been done better, at least in the modern era, than in Jacques Audiard’s “A Prophet.” When we meet him, Malik (Tahar Rahim, in one of the most scorching breakthrough performances of the last decade) is an illiterate street kid, raging against the world in an unfocused way. But under the harsh tutelage of Niels Arestrup’s incarcerated Corscian mobster, he finds a new purpose, and a new ambition, before the pupil ultimately supersedes the master. By the end, Malik is released, ready to cut a new swathe through the underworld, and there’s little doubt that he’ll be a huge and bloody success. Audiard’s tough, yet strangely poetic film works as a terrific crime tale, thanks in part to Rahim’s fierce central turn, at once haunted and dangerous. But it works just as well as a parable for how incarceration can often lead to criminals becoming more entrenched in a darker world, not less. This is a film about the creation of a mob boss, but we can have little doubt by the end just how effective a boss he’ll be. 

Don Corleone (Marlon Brando) in “The Godfather”
Almost immediately, Don Corleone entered the annals of the most iconic cinema gangsters in history — Marlon Brando’s pose, and his puffed-out cheeks, became so recognizable that you could pick it out in silhouette. Cast despite the reservations of the studio (and after Laurence Olivier passed), Brando revived his career to an Oscar-winning degree, as the faintly mumbly, cat-loving patriarch of the Italian-American crime family. It’s a crucial performance, in that Brando gives a Shakespearean heft to what could have ended up as a pulpy crime tale: the Don is a king in all but name, holding himself with an aristocratic poise even as he orders terrible things. He’s more Lear than Macbeth, though: old and aware that his time is passing, and unsure at the legacy he’s leaving for his children, or perhaps even from his children. It’s the weariness of Brando’s turn, the way that he longs for the violence, and even his own life, to be over, that is one of the things that give the film so much soul, and that makes this turn here simply peerless; the Godfather to this whole list.

A few others we thought of but didn’t make the cut included: Ben Gazzara in “Capone“; Daniel Day-Lewis in “Gangs of New York“; Tom Wilkinson in “Batman Begins“; Gabriel Byrne in “The Usual Suspects” (though he ain’t really the boss…); El Sol in “Sin Nombre“; Tony Servillo in “Gomorrah“; and Paul Muni in the original “Scarface.” But we just know there are others you love that we’ve skipped, so send us horse heads or sleeping fishes in the comment below.

–Nicholas Laskin, Oli Lyttelton, Jessica Kiang, Samantha Vacca, Gary Garrison

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