Of course when you're the head of a large group made up of criminals, it's hard to trust anyone. There's bound to be someone as ruthless as you, wanting your spot, or the cops you don't own, plotting to take you down. All the same, it's somebody's American Dream, have all the luxury and power you want, and all you have to do is figure out how to keep it. As unbelievable as it may seem, many of such stories are based on actual events (although some more loosely than others.)
I've tried not to dominate my list with the same actors, (although having two from Pacino was unavoidable.) and only include films where the boss has a prominent role. Please feel free to add your own suggestions. I'd love to hear what your agreements/disagreements. There are certainly many other worthy roles. I've also included links to full reviews on those films that I've covered in a past entry.
10. Brick Top (Alan Ford, Snatch)
Brick Top is a long way from a Corleone type. He controls the local boxing circuit and associated gambling with ruthlessness and hungry pigs. Turkish (Jason Statham) and Tommy (Stephen Graham) need to get their boxer onto Brick Top's books. After finally getting him to agree, they run into a group of gypsies and find one of their number, Mickey (Brad Pitt) can easily lay out their prized boxer with one punch. With their boxer incapacitated and very impressed with Mickey, Turkish thinks to have Mickey fight for them. Brick Top isn't happy with the switch and demands Mickey throw the fight. Mickey, however isn't good at following directions and knock the other fighter out immediately. Meanwhile Bricktop also has to deal with some would be thieves who happened to hit up one of his bookies, who unexpectedly came into possession of a corpse and are having trouble getting rid of it. He enlightens them as to his preferred methods: "the best thing to do is feed them to pigs. You got to starve the pigs for a few days, then the sight of a chopped-up body will look like curry to a pisshead. You gotta shave the heads of your victims, and pull the teeth out for the sake of the piggies' digestion. You could do this afterwards, of course, but you don't want to go sievin' through pig shit, now do you? They will go through bone like butter. You need at least sixteen pigs to finish the job in one sitting, so be wary of any man who keeps a pig farm. They will go through a body that weighs 200 pounds in about eight minutes. That means that a single pig can consume two pounds of uncooked flesh every minute. Hence the expression, "as greedy as a pig." And of course, Bricktop has a pig farm, and intends his advice to affect them very personally until they tell him about the diamond they're after. Brick Top gives Turkish another chance, burning Mickey's mother to death and destroying slot machines which are Turkish's other income as a a warning. Mickey doesn't follow orders again, getting Turkish and Tommy into deeper trouble. Brick Top sets out to exact his revenge, not realizing that Mickey expected it and set up his fellow gypsies to take him and his men out first. Alan Ford gives us a nasty and ruthless Brick Top, who exudes enough hatred with a look to frighten most normal people. His downfall is not realizing that Mickey doesn't follow those rules.
While certainly not DeNiro's best performance, he does just fine making the figure of Al Capone a large one. In the Untouchables we get him as a seemingly unbeatable opponent. Elliot Ness (Kevin Costner) is trying everything he can, but can't get near him, as much of the police force that Ness relies on is under Capone's control. It isn't until he listens to a little advice from agent Jim Malone (Sean Connery) who advises Ness "He pulls a knife, you pull a gun." Ness takes the advice, and starts hitting harder. This doesn't stop Capone, however, who continues his business as usual, threatens the lives of Ness' family (and Ness himself of course.) He declares, "I want you to get this fuck where he breathes! I want you to find this nancy-boy Eliot Ness, I want him DEAD! I want his family DEAD! I want his house burned to the GROUND! I wanna go there in the middle of the night and I wanna PISS ON HIS ASHES!" Capone even has some of Ness' men killed (including Malone.) Finally deciding to go after him for tax evasion, and getting him into court, they find an unbothered Capone, who's all smiles. His main hitman, Frank Nitti has been allowed by the corrupt mayor to bring his gun into court. Ness can't abide this, knowing Nitti killed Malone, and calls him on it, leading to a showdown, which ends with Nitti dead, and the revelation that the jurors were bribed and the judge is intimidated too. Ness manages to set things right and finally gets Capone into prison, but it wasn't easy.
8. Harry (Ralph Fiennes, In Bruges)
Harry carries himself more as a business man than a crime boss, conducting himself in a proper family man, while giving orders over the telephone. Harry has a very particular way he likes things done. In, "In Bruges"he has decided to kill one of his own hit men, Ray (Colin Farrell) and sends him to Bruges with friend and longtime associate, Ken (Brendan Gleeson) reasoning that Bruges is a town that's "like a fairytale" in order to give Ray a nice time before he's killed. Ray, however, despises Bruges and Ken isn't able to bring himself to kill him, and actually stops Ray from killing himself over his accidental shooting of an innocent little boy. (which is why Harry wants to kill him) When Ken informs Harry that he won't do it, Harry heads to Bruges himself and tells Harry that Ray should've killed himself the moment that he killed the kid, and that's what he himself would've done. He wounds Ken, rather than killing him, although Ken sacrifices himself anyway, to alert Ray. During an extended chase, where Harry takes great pains not to injure innocent people, he accidentally shoots a dwarf actor dressed up as a schoolboy, and is obliged to live up to what he had said earlier, immediately killing himself, while Ray, perhaps unwisely, tries to alert him to his error. Fiennes is terrific as a frightening but amusing and relatable boss, who truly believes in the code he insists on.
7. John Rooney (Paul Newman, The Road to Perdition)
John Rooney (Paul Newman) is the head of the Irish mafia in an Illinois town, controlling nearly everything that happens there. His top hit man is Michael Sullivan Sr., an orphan he took in when he was young and has great affection for.Rooney's actual son, Connor, however, is a psychotic loose cannon, who kills a man needlessly. Michael Sr. and Connor then discover that young Michael Jr. had hidden in the car and seen the whole event. Without his father's approval or knowledge, Connor attempts to have Michael Sr. killed, while he himself kills Michael's family with the exception of Michael Jr., who wasn't home. Sullivan goes on the run with his son, and approaches Al Capone's people, to try and get approval to kill Connor. They however, don't oblige and Sullivan starts robbing banks of strictly money held for Capone, hoping to pressure them to turn over Connor. He obtains information that Connor had been stealing from his father and shares it with John, but John already knew that and despite his feelings and affection for Michael, he can't turn on his own son. Sullivan meets John Rooney later that night, effortlessly picking off all of his men, before nearing Rooney, who he finishes off up close and face to face. Rooney understands, and tells him "I'm glad it was you." With the elder Rooney dead, Capone doesn't care about Connor and gives him up, although Michael still has a hit man pursuing him and a son to keep safe. Paul Newman gives us a memorable figure who we know has to go, but we still sympathize when Michael feels bad about it.
6. Frank Lucas (Denzel Washington, American Gangster)
Although Frank Lucas is the extremely successful head of a drug dealing organization, he differs from many crime bosses, in that you'd never know it. While certainly not above murder, or ruthlessness, he's more concerned with making money and keeping his ship in good shape. He patiently learns everything he can from his boss, Bumpy Johnson, until he dies and hands over the operation. Not happy with the status quo (inferior product, lots of hassle, not enough money) He arranges to go straight to the source, and rather than deal with the mafia, he brings his drugs in from Viet Nam. This gives him a pure product at a price the middlemen can't compete with. He takes pains to treat his people right, and instructs them not to be flashy. He's content to stay low profile if it brings the money in. However super honest Officer Richie Roberts (Russell Crowe) notices him at the one moment he forgets about keeping a low profile. With extreme perseverance, Roberts sets out to bring Lucas down. Once Roberts has him, Lucas, ever the businessman, agrees to be helpful for a lenient sentence, turning on his associates as well as all the dirty cops he dealt with. Denzel Washington makes Frank Lucas a crime boss who tries to care about his family and his neighborhood. Drugs to him are just product, and by his reasoning, if they weren't purchased from him, they'd be bought somewhere else. Denzel Washington handles the role quite capably, making Frank admirable for his ingenuity and intelligence.
5. Frank Costello (Jack Nicholson, The Departed)
Frank Costello is a powerful crime boss in Boston. He's admired by a young boy, Colin (Matt Damon) who Costello recognizes as a great possible resource and grooms him as he grows up to get on the Boston Police force to serve as his mole. At the same time, Billy Costigan (Leo Dicaprio) is going the opposite way, he'd like to be a cop, but his family background, makes him perfect for the police to use against Costello. Costello's group and the police both become aware of moles, and much effort is spent by both sides to find them. Colin however, finds unexpected news in his search, that Costello himself, is a mole for the FBI, leading Colin to question his motives and actions, and ultimately, it isn't Costigan that brings Costello down, but Colin, angry at the betrayal, and justified because Costello attempted to kill him when confronted on it. Of course Colin and Billy have business to finish up, but it's Costigan that put it all in motion. Nicholson gives us the ultimate manipulator, a man who has a use in mind for everyone he meets and ultimately proves that his only loyalty is to himself. As likely to have you killed as tell you a joke, he's a truly distinctive character who prides himself on details, yet can't possibly keep track of them all. Nicholson gives us crude charm and psychosis in one package.
Keyser Soze (Kevin Spacy, The Usual Suspects)
Soze is a different kind of crime boss in that no one knows if he exists or not. He's a malevolent figure who has put so much effort into his own reputation that his name is enough to frighten people. Criminals do jobs for Soze without even knowing they're working for him. Even when he's caught, they don't know they have him. Customs agent Kuljan (Chazz Palmienteri) knows something his off in his investigation of a horrible dock fire, and confronts the only survivor, Verbal Kint (Kevin Spacey) who has already cut a deal about his own involvement. Kint walks with a limp and appears the weak link in the group of criminals involved in the fire. He tells Kuljan an interesting story about how a heist was put together, portraying Dean Keaton (Gabriel Byrne) as a possible Soze, knowing that's Kuljan wants to hear. However, as Kint leaves the station, Kuljan realizes that many details of Kint's story were fabricated based on items Kint was looking at in the office. A fax comes over with a drawing of Soze, from a nearly dead eyewitness, and it looks just like Verbal. Kuljan rushes out to the street, where Verbal's limp has suddenly corrected itself and he gets into a waiting car, leaving Kuljan to ponder his words "The best trick the devil ever pulled was making people believe he doesn't exist." Kevin Spacey is great, playing essentially two parts, the clumsy Kint that we see, and the mastermind, Soze hidden beneath.
3. Frank White (Christopher Walken, King of New York)
Frank White gets out of prison with a vision to give his city a makeover. His first move is to eliminate a rival gang because he doesn't like the way they do business (child prostitution among other things.) He wants to give the city a new hospital. He considers running for mayor, and decides to give the city a new hospital. The hospital project is to be started with Frank's drug money. He offers a local triad a chance to get on it, but when they turn him down, he and his gang kill them all and take their hidden drugs. The police are soon gunning for Frank and his men and succeed in getting one of his crew to sell Frank out. Frank finds out and punishes the rat, but the police are all after him and take out most of his crew, but not without heavy losses themselves. Frank catches up with head detective Roy Bishop (Victor Argo) and explains the situation, as well as his plan to put bounties on the heads of all the cops involved. Bishop asks Frank if he thought he'd get away with all the killing. Frank simply answers "I never killed anyone that didn't deserve it." Bishop pursues Frank into a subway car, causing Frank to drop his Robin Hood image a moment, taking a woman hostage. He shoots and kills Bishop, who gets a shot off himself. Frank realizes he's been shot and dies himself pretty shortly. In one of Christopher Walken's best roles, he makes Frank a complex character, a man truly wanting to help, but not familiar with sensible ways of doing so.
2. Tony Montana (Al Pacino, Scarface)
Tony Montana comes to Miami, Florida from Cuba with nothing but aggression and desire. He agrees to deliver some cocaine and collect payment. The job goes wrong, but Tony gains the upper hand, walking away with both the cocaine and money. He quickly gets connected with a local crime figure, Frank Lopez (Robert Loggia) but soon outgrows the association, taking advantage of a trip to Bolivia to start setting up his own deals with Frank's supplier, Sosa. Tony wants more than working for someone else can provide. He leaves Lopez behind to make his own money and starts pursuing his wife Elvira (Michelle Pfeiffer) Frank, threatened by Tony's success, moves to have him killed, but fails. Tony calls Frank on his attempt, killing both Frank and a cop he associates with. His business is wildly successful, but into a hitch when he's busted by an undercover cop. Sosa gives Tony an option to avoid prison, calling in influential friends to protect Tony if he assists in the killing of a Bolivian journalist. When the journalist's family gets involved Tony kills the Bolivian hit man to save them. Sosa declares war on Tony, sending an army of his men after him. He seems indestructible for awhile but they keep coming finally shooting him from behind. Scarface shows us a man who wants everything and won't be stopped until he gets it and explores the limits of how much force is required to keep it. Pacino is brilliant as a practical force of nature, a man unwilling and perhaps unable to recognize any limitation except the final one.
1. Michael Corleone (Al Pacino, The Godfather)
Michael Corleone comes from a powerful crime family, his father Vito, being the Don of one of the "five families." Michael starts out removed from the family business, returning home from a stint in the Marines. He makes a point of telling his girlfriend that he isn't like them. Don Vito refuses the Virgil Sollozo's (Tattaglia family backed) request for support with his heroin operation, as he believes drugs will damage his influence. Don Vito sends one of his men to infiltrate the Tattaglia backed operation, but he's quickly found out and killed, followed by an assassination attempt on Don Vito himself. The eldest Corleone, Sonny (James Caan) handles operations for a while, but Michael soon gets personally involved. While visiting his father at the hospital Michael discovers he's unguarded. He saves his father and gets severely beaten, mouthing off to a corrupt cop. Sonny retaliates having the son of Don Tattaglia killed. Michael personally offers to kill both Sollozo and the cop who beat him. He succeeds, and then goes into hiding in Sicily. Sonny is soon killed, however and Don Vito agrees to meet with the five familes to settle the situation, discovering that it isn't the Tattaglia's but the Barzini's behind their troubles. Michael soon encounters enemies of the Corleones in Sicily barely escaping an assassination attempt. With the war in the US resolved, Michael returns home and takes over the Corleone business. He marries his old girlfriend and promises to make the family legitimate. Michael confuses the family with his actions but he receives advice from his father. He uncovers an attempt by the Barzini's to have him killed, but doesn't let on, instead staging a serious of killings which includes Don Barzini. When his wife asks him about one of the murders, he assures her convincingly that he was not involved, and ends the film as the true Don Corleone. Pacino's Michael is a compelling figure, and "the Godfather" illustrates wonderfully how his distance from the family gives way until he truly is the family and everything he said he wouldn't be.