He’s the Boss: The Screen’s Greatest Crime Lords

With Black Mass opening this week, here's a full clip of the screen’s most memorable gangsters.

The crime genre has been an integral part of movie history almost since the beginning: A Daring Daylight Burglary, a silent British short, was released in 1903, while the gangster movie arguably came along three years later with the American release The Black Hand. But the 1930s is when the genre really began to flourish, and it was around then — with films like Little Caesar (1931) and the original Scarface (1932) — that the archetype of the up-from-the-streets crime boss began to take shape through the personas of actors like Edward G. Robinson and George Raft.

It was decades later that the crime boss was reinvented again with The Godfather (1972), as the street thugs of earlier films gave way to men of wealth, taste and even political power (not to mention the ever-present homicidal impulses). In succeeding years, we’ve had an uneasy relationship with these screen-dominating characters — on one hand, their absolute power and even class are alluring, while on the other hand their dark psychosis and blackened souls (two traits brought to frightening life by Johnny Depp as real-life Boston kingpin Whitey Bulger, opening this week in Black Mass) offer a glimpse into the worst of humanity. They continue to fascinate us to this day, which is why compiling this list of the screen’s greatest crime bosses was, to borrow a phrase, an offer we couldn’t refuse.

23. James Cagney as Eddie Bartlett (The Roaring Twenties, 1939)

Cagney’s Tommy Powers never made it to boss in Public Enemy, but Bartlett clipped Nick Brown’s spaghetti to become co-head with Humphrey Bogart’s George Hally of a huge bootlegging operation in Raoul Walsh’s epic. Cagney rises from forgotten doughboy to unforgettable big shot. When a club snubs his singing sweetheart, he buys the joint. The off-key canary Panama Smith, played by Gladys George, was based on Texas Guinan, who ran speakeasies in New York and greeted customers with the phrase “Hello, suckers.” The always-energetic Cagney gives a tour de force as he rises up the gangster ladder only to stumble down its steps. (TS)

22. Mel Blanc as Mugsy/Baby Face Finster/Ant Hill Harry (Looney Tunes/Merrie Melodies shorts, 1946)

Like Jerry Seinfeld, I got most of my edumacation from cartoons and Bugs Bunny was probably the best teacher ever. Mugsy and his henchman Rocky, AKA Hugo, were introduced in the 1946 film Racketeer Rabbit because the bunny from Brooklyn had outsmarted all his other nemeses and needed fresh meat, um, carrots. Originally patterned on Edward G. Robinson and Peter Lorre, the characters wound up shaking down the rest of the Looney Toons universe before spreading their turf into Merrie Melodies. Mugsy held to the concept of Omerta and told Bugs Bunny to keep his lips buttoned. Baby Face Finster appeared in the 1951 Merrie Melodies short film Baby Buggy Bunny (directed by Chuck Jones) and got Bugs to launder the dirty money he nabbed from robbing the Last National Bank. (TS)

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21. Dolph Sweet as Chubby Galasso (The Wanderers, 1979)

The Galasso Brothers are the fat guys in the Hawaiian shirts who run the bowling alley. They are the face of the Mafia on the streets of the Bronx’s Little Italy. They settle neighborhood disputes and know everything that happens on the block. They take on racial tensions because “it’s a shame to see kids beatin’ each other’s brains out, especially when there’s no financial advantage.” Sweet, who you might know as the happily clueless father Mr. Caruthers on the “Best Line” episode of TV’s Taxi, plays Chubby Galasso in Philip Kaufman’s adaptation of the Richard Price novel as an approachable family capo, the kind of boss people who grew up in neighborhoods like that saw every day. (TS)

20. Bob Hoskins as Owney Madden (The Cotton Club, 1984)

Francis Ford Coppola directed the best gangster movie of all time with The Godfather and followed it up with an unabashed love letter to the genre in 1984. Madden owned Harlem’s hottest nightspot, The Cotton Club, but started out in the Gopher Gang and made his bones by dusting a rival Italian gang member. He went on to become the gangster all gangsters wanted to be. His personal driver was a young George Raft, who would become one of Hollywood’s most iconic tough guys with a flip of a coin. Madden retired from crime after the murder of Vincent “Mad Dog” Coll, who went out much the same way as Nicolas Cage did in the movie. Yes, he retired and when he did he opened up one of gangland’s greatest vacation spots in Hot Springs, Arkansas, where the cops nabbed Lucky Luciano. Hoskins plays Madden the way we want to remember him, enjoying the good life he worked so hard to achieve. (TS)

19. Wesley Snipes as Nino Brown (New Jack City, 1992)

New Jack City introduced an entirely new kind of crime boss. There had been African-American gangs and gangster movies, but Nino Brown and his gangstas, the Cash Money Brothers, kicked the jive to the curb. Director Mario Van Peebles was the son of hyper-realistic blaxpoitation provocateur Melvin Van Peebles, who helmed and starred in the beautiful Sweet Sweetback’s Baadasssss from 1971. Mario let Wesley Snipes have the time of his life. Snipes brings flash and furious fun to this gangster hero. You can see how the kids on his block all want to grow up to be in his crew. I admit, I usually root for the gangsters in gangster movies. But there is nothing Ice-T can do to make us root for him. Nino wasn’t just da bomb, he fucking invented it. (TS)

18. Edward G. Robinson as Johnny Rocco (Key Largo, 1948)

Johnny Rocco is the gangster who wants more. Rocco is the criminal emperor in exile. The first time we see Rocco, he is in the bath, chomping wetly on a cigar — a critic at the time said he looked like a crab outside its shell. Rocco is self-centered and greedy beyond compare. Only Robinson could have brought enough history and depth to a character to cow Humphrey Bogart’s returned war hero. Robinson played the iconic gangster Rico in Little Caesar and the mob boss who takes it on the lam to tend flowers and make wine in Brother Orchid. He gave a memorable turn as James Cagney’s crime boss in the pre-code Smart Money, which also featured Boris Karloff. Director John Huston copped the scene here, where Rocco cruelly forces Claire Trevor’s broken down moll Gaye Dawn to sing for her drink, from a real life incident with Bogie’s third wife, Mayo Methot. (TS)

17. Ving Rhames as Marsellus Wallace (Pulp Fiction, 1994)

As the employer of petty criminals Jules (Samuel L. Jackson) and Vincent (John Travolta), and the man who Butch (Bruce Willis) betrays by refusing to take a dive, Rhames exudes a quiet menace as the mysterious Marsellus. We get the sense that he’s involved in some strange business — What exactly is in that suitcase? Why does he have a bandage on the back of his neck? — and when he promises to go “medieval on yo ‘ass,” you believe him. And yet he has a code of honor as well: after Butch rescues him from the rapist Zed, Marsellus says they’re even. But you never doubt that could change in a second if Butch doesn’t hold up his end of the deal. (DK)

16. Humphrey Bogart as Baby Face Martin (Dead End, 1937)

Baby Face Martin is my favorite gangster of all time. The Dead End Kids of the Lower East Side look up to the guy who made it off the street and into silk ties, custom made. The name Baby Face Martin evokes a lone gunman, but his inspiration, Baby Face Nelson, led a gang. Martin is on the lam with his stooge, played by a brilliant Allen Jenkins, who brings humor, pathos and humanity to his jukebox-kicker. But the kids all want to be Bogart. They’re happy just to shine his shoes and when he shows them how to flick a five-cent pocketknife, they would die before they’d rat him out. An early version of how crews get built on the street. (TS)

15. James Cagney as Cody Jarrett (White Heat, 1949)

James Cagney perhaps defined the psychotic gangster with his electrifying portrayal of Cody Jarrett in this classic. Devoted to his domineering mother yet willing to gun down anyone who stands in his way, Jarrett is a true monster and Cagney’s embodiment of him echoes down through generations of villains from Al Pacino’s Tony Montana to Jack Nicholson’s Frank Costello (more on him in a sec). White Heat was voted the 4th best gangster film of all time in a poll conducted by the American Film Institute, and Cagney is one of the major reasons why. “Made it, Ma! Top of the world!” remains one of the all-time great goodbyes. (DK)

14. Jack Nicholson as Frank Costello (The Departed, 2006)

Costello is loosely based on Whitey Bulger, but you can also trace a direct line between Cagney’s Cody Jarrett and Nicholson’s Frank Costello. The latter, however, arguably amps up the gore, psychosis and air of invulnerability. Waving body parts around like hors d’oeurves, strolling through a bar with his shirt covered in blood as if he spilled a little wine on it, Costello’s devil-may-care attitude is matched only by the horror of what exactly he’s doing in that back room. Hedonistic, arrogant (he likes insulting the cops to his face) and exhibiting no moral code whatsoever, Nicholson’s over-the-top Boston boss is as depraved as they come. (DK) 

13. Robert De Niro as Al Capone (The Untouchables, 1987)

There are only a handful of true-life figures in this survey, and this is one of the most memorable. There may be no actual gangster more famous than Al Capone, whose name is practically synonymous with crime, and De Niro brings him to colorful, frightening life. He’s almost a cartoonish figure at times — such as when he weeps copious tears while watching an opera — but quickly erases that with a shocking act of violence like beating a man’s brains in at the dinner table with a baseball bat. De Niro put on 30 pounds for the role, adding an even more physical dimension to a man whose grip over Chicago seems unshakeable. (DK)

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12. Tom Wilkinson as Carmine Falcone/Heath Ledger as the Joker (Batman Begins, 2005; The Dark Knight, 2008)

Few superhero franchises have focused on crime bosses — as opposed to supervillains — in the way that Christopher Nolan’s Dark Knight trilogy did, and the two bad guys we’ve highlighted here represent two ends of Gotham City’s criminal spectrum. Carmine Falcone is an old-school mob boss, tough and cruel and unrelenting while clearly part of an established and familiar order, yet the Joker represents an escalation of the criminal element into outright terrorism as he solidifies his power over the city’s entire lowlife element. Both Falcone and Joker are Gotham at its worst. (DK)

11. Lee J. Cobb as Johnny Friendly (On The Waterfront, 1954)

“Stop breathing that clam sauce on me,” Friendly chides a future Herman Munster (an uncredited Fred Gwynne) and tells an entire history. This is a local union boss with enough juice to give future Godfather Marlon Brando (as Terry Malloy) a no-work job. On the Waterfront was directed by Elia Kazan as an explanation for naming names to the Commie hunters that were handing out pink slips in Hollywood. Kazan did a good job at portraying the realities of what was happening to dockworkers under the thumb of gangsters. Cobb may wear a suit, but he’s all street. He is gruff, but understanding. There’s not a rummy on the docks who can’t put the squeeze on him. When the feds start dusting off the hot seat for him he lashes out ruthlessly. The best part of Friendly is that he reverts to his street enforcement days and kicks the shit out of Terry Malloy himself. (TS)

10. Albert Finney as Leo O’Bannon (Miller’s Crossing, 1990)

Miller’s Crossing remains one of the Coen Brothers’ great (and somewhat underappreciated) films, not to mention a hell of a gangster picture that brilliantly pay homage to many other key movies and elements of the genre. As Leo O’Bannon, an Irish mob boss who lords over an unnamed city, Albert Finney is an imposing, powerful presence who spouts some fantastic dialogue (featuring a lot of made-up lingo by the Coens) and stops the show with a stunning tommy gun massacre scored to the strains of “Danny Boy.” It’s an unforgettable scene in one of the Coens’ most beautifully crafted early films. (DK)

9. Denzel Washington as Frank Lucas (American Gangster, 2007)

The great Washington plays one of the few true-life characters on this list, a Harlem drug lord who allegedly smuggled heroin into the country on board planes bringing back dead servicemen from Vietnam. Consolidating his power throughout the five boroughs of New York and beyond, Lucas plys his trade quietly and without drawing attention to himself — a mode of operation that lets him get incredibly far until he is finally noticed by the police and the DEA. Washington’s Lucas is crime boss as businessman — and he makes deals all the way to the end, when he turns informant on corrupt DEA officers and gets himself a reduced sentence as a result. (DK)

8. William Hickey as Don Corrado Prizzi (Prizzi’s Honor, 1985)

Hickey brought the perfect singsong lilt to his Sicilian family patriarch. He orders a killing as cheerfully as he offers a cookie over espresso. The Prizzi family was from the Prizzi province in Palermo. It took novelist Richard Condon four books to tell their story and Hickey wears it all on his face. You don’t even know he’s alive when you first see him. But then he opens his mouth and you’re even less sure. The old don sees himself in Maerose, played by Angelica Huston. She will never forgive Charley Partanna, the hitman played by Jack Nicholson, for humiliating her and he recognizes that as something she got from his DNA. He is fun and ruthless. (TS)

7. Paul Sorvino as Paul Cicero (Goodfellas, 1990)

“Paulie” — based on real-life Lucchese family caporegime Paul Vario — is not exactly a boss (he’s one rung down from the top job), but he carries himself like one and if you didn’t know how the structure of the Mafia worked, you might watch the whole movie thinking he was the Don. Sorvino is perfect in the role: quiet, intense and physically intimidating, he doesn’t have to use much more than a glower and a slap across the face to get his point across. We never see Paulie commit an act of violence himself, but if you feel those eyes boring through you, you might as well be dead. (DK)

6. Daniel Day-Lewis as Bill “The Butcher” Cutting (Gangs of New York, 2002)

The Five Points district of lower Manhattan was a crime-infested slum for decades, but it might not surprise you to know that it was also the center of political power in the city — at least according to Martin Scorsese’s sprawling, messy epic, which positions the psychotic Bill Cutting as gang boss, enforcer and kingmaker for the Big Apple’s notorious political operative Boss Tweed. Cutting, based loosely on other local figures of the era (the 1860s) is a force of nature and a freak: hunchbacked and wild-eyed, Day-Lewis gives a jolting, shuddery performance that provides a glimpse into the little-known darker corners of this era of American history. (DK)

5. Kevin Spacey as Keyser Soze (The Usual Suspects, 1995)

“The greatest trick the devil ever pulled was convincing the world he didn’t exist.” That unforgettable line (from poet Charles Baudelaire) is the key to the terrifying power of criminal mastermind Keyser Soze, who is seemingly invisible throughout the movie — a force of nature around which the film’s events coalesce — and yet is hiding in plain sight the entire time. The way that director Bryan Singer and screenwriter Christopher McQuarrie build up the legend of Soze, making him seem almost supernatural, is brilliant and makes the final reveal even more devastating. (DK)

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4. Tahar Rahim as Malik El Djebena (A Prophet, 2009)

Nearly all the films we’ve got on this list take place in America, with side trips to Italy, Cuba and a few other locations. A Prophet thrusts us into a gritty French prison, where we are introduced to petty criminal Malik and watch his slow, steady rise through the power structures of the jail, weaving his way through Corsican and Muslim gangsters until he emerges as the head of a powerful drug-running enterprise. The brilliance of Jacques Audiard’s crisp, superb epic is how it makes us root for Malik even as he become more hardened and ruthless while venturing down a path from which there is no turning back. Yes, he’s a family man too, but we have to wonder in the end whether there’s any room for love in a man like Malik. (DK)

3. Al Pacino as Tony Montana (Scarface, 1983)

Pacino played two iconic gangsters in his long career (more on the other one in a minute) and Tony Montana, the more hot-headed and psychopathic of the two, ushered in a new dimension to Pacino’s previously measured acting style. Tony makes his mark on Miami in blood — stabbings, shootings and a trail of brutalized corpses litter his rise to absolute power over the cocaine trade — and never shows one iota or remorse or even something resembling humanity. Montana is a monster, drunk on power and money, and Pacino plays him as an attack dog of unrelenting fury, with just enough charm and humor to make him gloriously watchable and quotable. (DK)

2. Al Pacino as Michael Corleone (The Godfather Part II, 1974)

As vicious and fiery as Tony Montana is, Pacino’s earlier turn as Michael in the first two Godfather films is controlled and icy — making his outbursts of physical or verbal violence even more terrifying. Michael “becomes” the Godfather over the course of the first film, slowly losing his empathy and humanity, but in the second entry Pacino truly shines as an increasingly paranoid and ruthless Michael destroys every single thing in his life, including his family. Watch when Michael’s wife Kay (Diane Keaton) reveals that she had an abortion — “because this must all end” — and observe how his shock turns into cold, blind rage. Pacino was also terrific as a tired, regretful Michael in The Godfather Part III, but Part II is where Pacino is at his most dread-inducing. (DK)

1. Marlon Brando/Robert De Niro as Vito Corleone (The Godfather and The Godfather Part II, 1972/1974)

Could anyone else really be at the top? Marlon Brando’s slow-moving, stately Don Vito is a man of few words who emanates gravitas and is perhaps the single most iconic crime boss in all of popular culture. Brando (and Francis Ford Coppola and Mario Puzo) introduced a new kind of gangster: a man who could move in “respectable” circles and still order untold numbers of deaths at the hands of his loyal footsoldiers, yet enjoyed playing in an orange patch with his grandson. Brando’s work is for the ages, but we must also honor De Niro’s interpretation of a young Vito in The Godfather Part II, fresh off the boat and working his way through the danger-filled streets of early 20th century Little Italy. De Niro’s Vito is more primal and instinctive, but contains glimmers of the brooding, wise Don to come. (DK)

Black Mass is out in theaters Friday (September 18).