Al Pacino and the Many Faces of the Wiseguy: Some Thoughts on Scarface, Carlito’s Way, The Godfather and Donnie Brasco

By Adam J. Pearson

Carlito’s Way and Scarface are two of the undisputed greatest mafia films of all time. Both films excel in their rich, gritty, realism approach to the mafia genre, their high-quality acting, their skillful cultivation of atmosphere, their iconic cinematography, and excellent script-writing. The two films also invite comparisons with one another due to their many similarities; both films deal with figures within non-Italian organized crime families in America (Scarface, with a Cuban refugee family and Carlito with a Puerto Rican family), both films were directed by Brian de Palma, both films star Al Pacino as their central protagonist, both films deal with the rise and fall of a mobster, and both films were regarded as controversial for their vivid portrayals of graphic violence.  However, the two films also differ in a variety of interesting and significant ways; together, they present pictures of two very different kinds of mobsters expressed through the theatrical brilliance of Al Pacino.

On the surface, both Scarface’s Cuban refugee Tony Montana (Pacino) and Carlito’s Way’s eponymous former mobster seem to have a number of things in common. Both figures are incredibly charismatic individuals as both films illustrate from their very beginnings: Montana’s interrogation by police officers and Carlito’s opening courtroom speech draw our attention and fascination as audiences. Both figures are skilled shooters with no hesitation in killing when they need to. Both figures had some hand in drug dealing rackets in the past or present. And in the past at least, both figures were driven by a great love of power and wealth achieved at all costs.

However, as the movies progress, the two towering mobsters deviate considerably. Montana, who initially earns our sympathy through his incredible rise through the ranks of the underworld from rags to riches and his commitment to a twisted version of the ‘American Dream’, ends up becoming a drug-ridden, miserable man. As the film progresses, we watch as his charisma is steadily replaced by a kind of pathetic fallenness that alienates him from his once beloved Elvira, who, like him, devolves into an emotional, wary, depressed, and drug-addled fallen version of her former self. In contrast, Carlito is not a figure rising through the ranks of crime; he has already had his rise and done his time for it before the film even began. Instead, over the course of Carlito’s Way, De Palma presents a man who is trying to turn his life around, to leave behind the wiseguy lifestyle that he used to lead.

Like Montana, Carlito is pursuing a dream, but it is not a dream of wealth acquired through crime, but of a respectable, legal lifestyle as a used car salesman.  Montana’s dream of love, power, and criminally-acquired wealth alienates him from his beloved; in contrast, Carlito’s dream of a crime-free paradise with his beloved brings him closer to his own love. Whereas Montana and Elvira get to be together and fall together, Carlito is always working towards a moment of freedom from his criminal past and its seedy underworld, a vision of ‘paradise’–itself a significant motif throughout Carlito’s Way–that he can share with Gail.

The central figures in both films ultimately meet an untimely end as a result of consequences set in motion by their own past actions, but when they do, Tony dies with Elvira very far away and Carlito, with Gail very much by his side.  The moving end credits to Carlito’s Way visually capture this motivating force of the dream of a crime-free paradise as Joe Cocker’s “You Are So Beautiful” movingly plays on in the background.  The sight of a poster of a tropical paradise into which Carlito projects Gail dancing is his last image on this Earth and De Palma brilliantly draws us into his final vision, the dream he worked so hard to achieve, but tragically lost when it was only moments away from him.

Carlito and Gail in “Carlito’s Way”

In these two films, Pacino presents us different visions of the archetypal figure of ‘the gangster,’ ‘the wiseguy,’ or ‘the mobster.’ The wiseguy tends to be, as his name suggests, highly intelligent and educated in the underworld spaces through which he moves.  He knows the complex codes that govern mafia life–though Tony violates them by pursuing his boss’s girlfriend and Carlito stands by them almost to the end–and understands the subtle games that gangsters play with one another.  As an archetype, the mobster is often referred to as ‘the badguy,’ but Pacino’s portrayals in these two films complicate this simple designation.

Tony Montana is doubtless a bad guy in many ways by the conventional definition of the term; he kills without hesitation, he makes his living off of the drug addictions of others, and he lies, cheats and steals repeatedly, but he has sympathetic moments of basic humanity and caring as well. Montana strikes us less as a heartless psychopath than an overly bold, desperate, cynical, and disillusioned man trying to make his way in the criminal underworld.

Like Tony Montana, Carlito also once lived the gangster life and pursued wealth and power through racketeering, but in the film, we meet him at a time when he is a badguy trying to be good, a man trying to ‘break good’ in contrast with Breaking Bad’s Walter’s transition into badness.  Throughout Scarface, Montana repeatedly gets himself into bad situations by pushing forward and causing many of the conflicts he faces. Carlito, in contrast, does everything he can to avoid such scenarios, but tragically finds his past continually sucking him back into the seedy, dangerous world is determined to escape.

If Montana is the mobster at the height of the gangster lifestyle, both loving and hating it at the same time, Carlito is the man of the street who is trying to move from gangster to former-gangster, from criminal to straight-shooter.  If we feel some sympathy for Montana, when he goes out in a bang in Scarface‘s climactic final scene, we feel genuine sadness for Carlito, who despite all of his best efforts, fails to achieve his sincerely well-intended dream.

If Montana is an ambiguous antihero or even, arguably, a villain, Carlito is a tragic hero; his own underworld values, especially his misplaced loyalty to his lawyer Kleinman (Sean Penn) are the tragic flaws that bring about his downfall. It is truly disheartening when Carlito falls out of undue loyalty to Kleinman, who does not deserve it either by the code of the law–because he is a crooked lawyer who bribes juries, works for the mafia, and gets hard criminals off–or the code of the street--because he betrays Carlito and even frames him to the FBI. Loyalty is Carlito’s tragic flaw even as it is a fundamental value within organized crime; if Montana is a tragic hero in any sense of the word, his central flaw is his arrogant greed, his lust for power and wealth at all costs, which ends up destroying him.

In addition, Pacino has not only represented different facets of the archetype of the gangster, the organized criminal, in these two films; he has also given us striking visions of the mobster in the Godfather trilogy and Donnie Brasco. In The Godfather Pacino incarnates Michael Corleone, the new ‘Godfather’ to replace his fallen father, Vito. Michael is a shrewd, streetwise, and highly intelligent man who gives up trying to resist his family’s criminal ways and ends up taking out all of the other bosses of the fictionalized Five Families. This scene, in which murders of the bosses are juxtaposed with a Christian communion while Michael prays along with the priest, wonderfully illustrates the strange fusion of Christian values and Mafia values which would, from that same perspective, be regarded as Satanic and ‘deadly sins.’ Michael Corleone is a man at the height of his power and the top of the mafia hierarchy as a boss with a consiglieri reigning over multiple capos (captains) each with their own soldiers and connected and associated guys beneath them.  In the Godfather Parts I and II in particular, Corleone’s intelligence, wisdom in the ways of the street and the politics of the mafia, leads him to prosper as a towering figure of underworld power.

In striking contrast, Pacino’s portrayal of Lefty “Guns” Ruggiero in Donnie Brasco could not be father from Michael Corleone. Based on the true Lefty Ruggiero from the Bonanno crime family, which was courageously infiltrated by FBI Agent Joe Pistone, Pacino’s Lefty is nearly powerless compared with the towering Corleone family boss. Lefty is a made man with many mafia hits under his belt, but he remains at the bottom of the mafia hierarchy; he is not a boss, not an underboss, nor even a capo. All of his life’s dedication and illegal earnings for the family come to nothing while the much younger Sonny Black rises up through his family’s ranks. If Michael Corleone is the monumental mafia boss, Lefty is the lowly soldier, hustling on the frontlines for advancement he never earns.

Al Pacino as Lefty “Guns” Ruggiero (far right) in Donnie Brasco.

In conclusion, in Scarface, Carlito’s Way, The Godfather, and Donnie Brasco, Al Pacino presents the many faces of the complex figure of the mobster, a figure of admirable intelligence and questionable means to power. Pacino embodies the high boss (the Godfather), the fallen drug kingpin (Scarface), the lowly soldier (Donnie Brasco), and the former mobster seeking the straight and narrow his own Way (Carlito’s Way). Indeed, Carlito’s “Way” is his “way out” of the criminal underworld and into a happy, loving, legal lifestyle; unfortunately, in the end, he is swallowed up by the very world he attempts to escape. His Way ends, not in love, but in death.

All of Pacino’s wiseguys have their sympathetic aspects and their faults; never do we get the sense that they are straightforwardly despicable figures. Pacino never plays them that easy and these films are not 19th century melodramas with clearcut divisions between heroes and villains. Even when these characters do hateful things, they remain strangely charming, sympathetic, even lovable, largely due to Pacino’s brilliance as an actor. In a similar way, Breaking Bad‘s Walter White teeters on the border between despicable and sympathetic, one minute earning our sympathy, and the next minute, losing it.  Pacino’s mobsters embody vast opposites: virtues such as loyalty, courage, and intelligence and vices such as murderousness, deceptiveness, and thievery; success and failure; old age and youth; good intentions and bad ones.  If these diverse portraits teach us anything, it is that the mobster is a complex figure that eludes facile judgments, a multifaceted human being who lives in a world where smiles hide daggers, crime pays, and graves and jail cells are only one wrong move away.


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