Like a Boss: the Best Performances by Actors Portraying Real Life Mob Chiefs

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Filmland has been full of fictional mob bosses heavily inspired by their real life counterparts, back to the days of the original 1932 Scarface film, and its ersatz Al Capone character “Tony Camonte.” In later years, gaining some space from the actual lives and events has allowed Hollywood to straight-on portray America’s legendary barons of crime many times over, real names and all. Even as the quite schlocky looking “Gangster Squad” barrels towards theaters this month with Sean Penn croaking out “sociopathic mobster 101” dialogue as L.A.’s infamous Mickey Cohen, the question begs answering: Which actors have done their real life hoodlums the proudest? It breaks down like this:

5 Harvey Keitel as Mickey Cohen, Bugsy (1991)

Harvey Keitel (along with cast-mates Warren Beatty and Ben Kingsley) was nominated for an Oscar for his work as crude, tough-talking yet impeccably dapper Mickey Cohen, who would go on to rule Los Angeles following Bugsy’s death after having served as Siegel’s right hand. This film portrays the two’s initial meet as anything but cute, as Cohen loudly threatens Siegel that he will “blow his Adam’s apple down his spine.” From there the two craziest Jewish mobsters in history become inseparable partners in crime, Cohen, being the short, to-the-point yin to Siegel’s tall, flighty yang. After his initial outburst, Keitel spends most of the movie providing a subdued level head to Bugsy’s unrealistic scheming, and constantly referring to AnneteBening’s Virginia Hill as “Victoria” much to Siegel’s chagrin. One wishes an epilogue had been filmed detailing Cohen’s real life, gun-blasting storming of an L.A. hotel lobby in search of Siegel’s killers.

4 Ray Danton as Legs Diamond, The Rise And Fall Of Legs Diamond (1960)

The television hit The Untouchables arriving in the 1959 spurred a kind of wave in cinema looking back on the real gangsters of yesteryear, which would last for about the next decade and a half. Every notable mobster and bank robber of the Prohibition/Depression era received their own biopic at some point in that span, with the studio that almost singlehandedly had made the gangster a movie star in the 30s, Warner Bothers, kicking things off by telling the story of Jack ‘Legs’ Diamond. Diamond, an Irish-American racketeer who warred with Dutch Schultz and guarded Arnold Rothstein, was second only to Al Capone in Prohibition Era notoriety, and though the film plays quite loose with several facts, Danton succeeds in capturing the cocky, flamboyant essence of the Diamond seen in newsreels and photos, working his way up with a smile and a gun. Danton was so good in fact, he was made to return in the role when WB made their biopic on Schultz, 1961’s Portrait Of A Mobster.

3 Dustin Hoffman as Dutch Schultz, Billy Bathgate (1991)

Arthur “Dutch Schultz” Flegenheimer, the ruthless Bronx beer baron who terrorized 1920s and 30s NYC with a series of violent conflicts before being mowed down with his inner circle quite spectacularly in 1935, has been portrayed a few other times in film over the years. Standing above performances like James Remar’s roaring cro-magnon version in 1984’s the Cotton Club, and Tim Roth’s one note cartoon psycho from 1997’s Hoodlum, is Dustin Hoffman’s very believable, very menacing take from this adaptation of E.L. Doctorow’s historical fiction novel. Speaking in a low, weighty Bronx honk, Hoffman is every inch the slovenly, exasperated Schultz at the end of his career, fighting a last stand as his enemies, both legal and extralegal, close in on all sides. Though the film is told from the point of view of a completely fictional character, the young gang gofer of the title, Hoffman gets to faithfully recreate many real, recorded instances from the Dutchman’s reign, such as his personal dispatching of treacherous lieutenants Bo Weinberg and Julie Martin, the former to a watery grave in cement shoes, the latter (in one of the film’s best scenes) dealt a spontaneous gunshot to the mouth.

2 Warren Beatty as Benjamin “Bugsy” Siegel, Bugsy (1991)

The role of the notoriously vain and unstable Jewish-American kingpin who came west from NYC to oversee L.A. rackets and would ultimately help plant the seeds of the Las Vegas we know today is a perfect fit for Warren Beatty, even if he may have already been a tad old for the role. Bugsy is portrayed here as a playboy yuppie mob boss, fixated on glamour and self-improvement (he’s prone to sitting in front of tanning lamps and practicing elocution) as he hobnobs with movie stars and royalty on Hollywood’s social circuit. The film does well to also make good use of the true-to-life notion that no one ever used the widely known nickname of the title to the thoroughly unhinged Siegel’s face, lest they be granted certain bodily harm. Whether beating mob compatriots within an inch of their life, or pressing friends on how good he actually looks in newspaper photos, Beatty brings one of history’s flashiest and most interesting crooks to proper life, and earned an Oscar nomination for his efforts.

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

In what actually amounts to a smaller role than one would expect, De Niro dominates (and amuses) in every fleeting scene he appears in as the most notorious gangster of all time, bootlegging king Alphonse Gabriel Capone. Very accurately alternating between Capone’s well-known traits of big lug jocularity/charm and explosive, violent temper, in a film where accuracy is apparently not any kind of priority. De Niro scores as the Brooklyn-born hood that ruled the Windy City during Prohibition thanks to in large part to his own personal dedication; he actually went throughthe trouble of gaining weight and shaving back his hairline to resemble the portly, early-balding Capone more closely, and even tracked down his then still-living tailor for wardrobe assistance. The baseball bat scene, where Capone bludgeons a traitorous underling with the aforementioned instrument in front of an entire banquet to make him an example, is legendary, yet disappointing in its infidelity to the actual events: In real life, Capone bludgeoned three guys at that banquet, not one.

Honorable Mention

Ray Stevenson as Danny Greene in Kill The Irishman (2011)
As the articulate, athletic Cleveland union honcho who defied the Mafia and set off a car bomb–heavy gang war in the 1970s, Stevenson shapes what ultimately amounts to a more admirable man than most gang lords.


Laurence Fishburne as Ellsworth “Bumpy” Johnson, The Cotton Club (1984) and Hoodlum (1997)
As the black crime boss who ran Harlem between lengthy prison stays from the Jazz Age to his death in 1968, Fishburne projects Bumpy’s intelligence and steely pride in not one, but two performances, in two films focusing on Dutch Schultz’s 1930s encroachment into the neighborhood.


Ben Kingsley as Meyer Lansky, Bugsy (1991)
The shrewd and ever-wise Lansky (the inspiration for Hyman Roth of The Godfather mythos), who managed to die as an extremely wealthy elderly man in the 1980s without having spent hardly a day in jail, is done justice here, portrayed as a very concerned friend to erratic boyhood chum Siegel.


Rod Steiger as Al Capone, Al Capone (1959)
Looking more like the real deal than probably any other actor to portray him , with his chubby cheeks and pouty lips, Steiger paints an indelible portrait of slob-on-the-rise Capone, in a fairly accurate minor gem that came on the heels of TV’s Untouchables.


Denzel Washington as Frank Lucas, American Gangster (2007) Despite the real Lucas being pretty much everything Washington’s portrayal was not (loud, ignorant, flashy, not quite handsome), Denzel’s unforgettably dignified portrait of criminal ambition in 1970s Harlem is one for the ages.


Anthony La Paglia as Frank Nitti, Nitti: The Enforcer (1988)
This film and Italian-Australian actor LaPaglia who captures Nitti’s calm, quiet reserve, get credit for setting the record straight about Nitti, after 1987’s The Untouchables painted him as a slippery hitman who was tossed off a building by Eliot Ness. In truth, Nitti took over after Capone’s incarceration, and the only person he most likely personally killed was himself.


Moral of the story: Crime does pay, in great performances. And also, you should probably watch Bugsy.

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