As one of the most esteemed screen actors of all time, Al Pacino has made a career out of playing complex good and bad guys alike. His most iconic roles often toe the legal line, if not overstep it entirely, in such classic films as The Godfather, Scarface, Carlito's Way, and more. It's a testament to Pacino's acting ability to instill such criminal characters with sympathetic humanity.
With Pacino set to play Aldo Gucci in House of Gucci, Ridley Scott's new dramatic crime thriller due this Thanksgiving, it's only right to take a look back at the venerated actor's most antagonistic roles to date. From Michael Corleone and Tony Montana to John Milton and more, there are many to choose from.
Sonny Wortzik - Dog Day Afternoon (1975)
Although his motives turned out to be incredibly tender and touching, the fact remains that Sonny Wortzik (Pacino) is an armed thief who puts the lives of several innocent people in danger during the infamous day-long bank robbery. Based on the real-life criminal John Wojtowicz, Pacino still manages to imbue the notorious movie bank robber with compassion.
While the volatile small-time hood threatens violence, he rarely demonstrates it and even begins to treat his hostages with more clemency than his accomplices. Sonny robbing the bank to pay for his partner's gender confirmation surgery is noble in its intention, but the way he goes about it ends up doing way more harm than good. Pacino earned an Oscar nod for his jittery yet exhausting performance.
Roy Cohn - Angels In America (2003)
Yet another real-life villain who Pacino was able to paint in a sympathetic light is Roy Cohn in Angels in America. Cohn was the notorious anti-Communist lawyer for Joseph McCarthy during the Red Scare of the 1950s and later became an influential right-wing fixer who wielded tremendous political power.
Cohn's hidden identity as a gay man comes to light when he's stricken with AIDS. He looks back at his life on his death bed upon being visited by the ghost of Ethel Rosenberg, a known Communist sympathizer. Pacino redeems Cohn with heartfelt pathos that shows that not even the biggest baddies are 100 percent pure evil.
Phil Spector - Phil Spector (2013)
Although David Mamet's HBO biopic Phil Spector primarily focuses on the relationship between the disgraced music mogul (Pacino) and his defense attorney Linda Kennedy Baden (Helen Mirren), the trial concerns the real-life figure's murder of Lana Clarkson in 2003.
For all the good he did in the music business, Spector's life took a turn for the worst, with Pacino earning plaudits for his portrayal of the villainous title character. It's always difficult to play such a complex and flawed real-life person, yet Pacino manages to challenge viewer expectations of the notorious public figure.
Lefty Ruggiero - Donnie Brasco (1997)
As the aging mafioso with a conscience, Lefty Ruggiero is another intrinsic villain that Pacino is able to make viewers feel conflicted about. He's lied, cheated, stolen, and killed in the past, but unwittingly sticks his neck out for Donnie Brasco (Johnny Depp), an undercover cop who has infiltrated the mob.
As an organized criminal by nature, Lefty is surely a villain. However, his biggest sin is crossing his own crime family by vouching for a cop, which, despite his heart being in the right place, ends up costing him his life. At the end of the highly-acclaimed gangster movie, Lefty turns out to be a villain for the police, as well as his own mob, with Pacino finding the right balance as a man with little agency trapped on both sides of the law.
Big Boy Caprice - Dick Tracy (1990)
As cartoonish and histrionic as it may be, Pacino earned an Oscar nomination for his turn as mafioso Alphonse "Big Boy" Caprice in Dick Tracy. As Dick's (Warren Beatty) public enemy number one, Caprice shows no scruples whatsoever in his attempt to bring the titular detective.
Buried under mounds of makeup to increase his intimidating nature, Caprice exudes a vindictive Napoleon complex as he kills his own mob boss in order to usurp his power, kidnaps his own girlfriend Tess (Glenne Headly), and holds her hostage without an ounce of remorse. Pacino has a ball chewing the scenery, proving a worthy adversary to one of the most beloved comic book characters on record.
Carlito Brigante - Carlito's Way (1993)
A decade after working with Brian De Palma on Scarface, Pacino turned in one of his best villainous performances in Carlito's Way. The titular criminal tries desperately to escape a life of crime, but cannot shake his bad habits, leading to unconscionable betrayal, extreme violence, and mass murder.
As an ice-cold gangster with zero attachments, Carlito's wicked nihilism enables him to turn on his friend, lawyer, and partner, Kleinfeld (Sean Penn), and have him killed without a second thought. Carlito's only redeeming quality is leaving money behind for his girlfriend and their unborn child, but by then, it's too late for him to see the fruits of his charity.
Jimmy Hoffa - The Irishman (2019)
As one of the most infamous organized criminals in history, Pacino was able to bring Jimmy Hoffa to life with tremendous credibility in Martin Scorsese's The Irishman. Convicted of jury tampering, bribery, conspiracy, and mail and wire fraud, not to mention ordering countless mob hits, Hoffa is as unlawful as it gets.
But like the best of Pacino's villains, the actor is able to establish a modicum of redemption in the character, namely seen through his relationship with his young daughters, his loyal friendship with Frank Sheeran (Robert De Niro), and his fascinating kinship with JFK as the head of the Teamsters union. While Hoffa's villainous reputation precedes itself, Pacino finds nuance in the character that reinforces his humanity.
Michael Corleone - The Godfather (1972)
While Michael Corleone is arguably Pacino's finest role to date, the fact that he was born into a life of organized crime without much agency to escape his family business makes his villainy somewhat excusable. Then again, killing his own brother Fredo (John Cazale) to preserve his own power is about as ruthless as it gets.
After reluctantly taking over Vito's empire, Michael brutally waylays rival mafia crews before learning his brother sold him out. Michael becomes eviler as time passes, assuming the head of the most powerful Italian crime family by eliminating rival crews, paying off the police, making shady political deals, and the like.
Tony Montana - Scarface (1983)
As the cocaine-addicted, chainsaw-wielding, machine-gun-toting drug lord Tony Montana, Pacino turns in one of the most blistering villainous performances of his career. While in many ways, the story is an underdog rags-to-riches flipside of the American dream, Tony is simply one cruel customer.
Driven by a craven sense of greed, the power-drunk Tony climbs the ranks of the Miami drug scene by outwitting, out-muscling, and flat-out murdering his rivals, including connected mafia bosses far above his own ranking. The ferocious final shootout is the stuff of cinematic legend, with badass Tony Montana going out in a hail of gunfire that proves his malevolent and murderous M.O.
John Milton - The Devil's Advocate (1997)
By literally playing the devil incarnate, Pacino ensures that his most villainous role is that of John Milton in The Devil's Advocate. What makes the character so evil is his deceptive disguise as the head of a law firm and the Faustian bargain he presents to new recruit Kevin Lomax (Keanu Reeves).
Additionally, it's the mendacious manipulation of Kevin that proves most sinister, as Milton assigns him a legal case that takes all of his attention away from his wife Mary Ann (Charlize Theron), making him choose between career success and familial bliss. Worse, Milton orchestrates murder to get Kevin to decide his precarious fate. In reveling in the mayhem, Pacino gives new meaning to the phrase "a devilish grin."