It’s somewhat fitting to be writing about mob movies only a few short miles from where Al Capone’s South Side Chicago gang once ran a bootlegging empire through brute force and backroom politics. And it’s downright surreal and disturbing to be only a short stroll from where the infamous Valentine’s Day Massacre occurred in 1929 — allegedly Capone’s bloody blueprint for settling gangland scores.
Capone died nearly 70 years ago, but you still can’t mention his name in Chicago without perking ears and sparking imaginations. He’s as iconic in this town as Barack Obama, Ernie Banks, or Mrs. O’Leary’s Cow. An amalgam of historical figure, favorite son, and folk hero — a combination that speaks to something remarkably peculiar about the types of characters (both real and fictional) who capture our imaginations.
The strangest feeling when watching a mob film comes when you pause for a moment, acknowledge that the character you’re rooting for is a murdering sociopath, and immediately shrug off that realization. How do we so cavalierly rationalize the fact that we’re often pulling for a villain — something we’d never do while watching, say, a superhero movie? Wait, both sides are villains in this movie. Yeah, but I’m rooting for the good villains. Partly, we’re living out fantasies through onscreen bosses and button men who follow a code that, while often brutal, seems to get results far more efficiently than the avenues available to the rest of us legit schmucks.
But more so, the mobsters we’re allied with as viewers — from Vito Corleone to Tony Soprano — tend to be incredibly likable. They’re family men, loyal friends, funny guys, and often “respected” members of their communities. It’s these same qualities, then, that make it all the more terrifying when that switch flips and a fella who looks like the type we’d invite to a poolside barbecue at our house starts practicing amateur dentistry on another guy using pliers and a parking meter.
I think that’s the appeal of many mob movies, really. We’re simultaneously captivated and terrified by the violent, heinous acts committed by men who seem like good enough fellas — if you ignore the body in the trunk. Sure, sometimes the shock of a mob hit stems from sheer brutality or pints of blood donated to the surrounding walls. But just as often it’s the sudden jump from a world we understand to an underworld we can barely fathom, our favorite gangster morphing from nice guy to wiseguy in the time it takes to say fuhgettaboutit.
These are the mob hits that shock us several viewings and, in some cases, many decades later. If you have other shocking hits you’d like to rat about, feel free to spill them in the comments section. And if you don’t agree with us, just remember: It’s not personal. It’s strictly business.
10. Push It To The Limit
Hit Man: Tony Montana
Who Got Whacked? Manny Ribera
Look, Tony Montana (Al Pacino) is a fucking raving lunatic. Point to any scene in all 170 minutes of Brian De Palma’s sprawling gangster masterpiece and you’ll have solid evidence of his madness. Subtlety isn’t his strongest attribute — after all, he screams as much as he violently kills — which is why everyone who has ever met him is absolutely terrified, from his enemies to his family to his friends. His closest pal Manny Ribera (Steven Bauer) probably should have been a little more wary. Yes, they grew up together, survived refugee camps together, and climbed up the ranks together, only that don’t mean jack shit to a guy like Tony. Especially a coked-out Tony. And especially a coked-out Tony who discovers you’ve been shacking up with his sister, Gina (Mary Elizabeth Mastrantonio). Blame it on drugs, reckless abandonment, blind rage, or a severe Oedipal complex, but when Tony takes out Manny for simply being a good guy to his sibling, well, he turns into a real jerk. –Michael Roffman
09. A Knife to a Gunfight
The Untouchables (1987)
Hitman: Frank Nitti
Who Got Whacked? Jimmy Malone
Perhaps we were always supposed to know Malone (Sean Connery) would get iced. After all, he’s the lone wolf among his trusty Untouchables on a redemptive streak — a disgraced beat cop with an honest soul and Irish wit. Without him, Elliot Ness (Kevin Costner) would be wandering around the streets of Chicago blind, only hoping to do some good. No, Malone has seen it all, and he knows how to take down Capone by pushing all the forbidden buttons. But those buttons can only be pushed so far, which is why when Malone harasses police chief Mike Dorsett (Richard Bradford), he’s signed his own death slip. He knows this, a harsh realization he accepts long before that rainy alleyway fight with Dorsett. But he’s a born fighter. So, he gets the goods and bites the bullet. Many of them. And it’s one of the most ruthless and agonizing on-screen deaths this writer’s ever shed tears to, one that stings decades and multiple viewings later. ::cue Ennio Morricone’s “Death Theme”:: –Michael Roffman
08. One Hole, Two Brothers
Hit Men: Frank Marino and the rest of Nicky Santoro’s former crew
Who Got Whacked? Nicky and Dominick Santoro
It’s not personal. It’s strictly business, my ass. Okay, we get it. Nicky Santoro’s (Joe Pesci) reckless antics had become bad for business. But a good, old-fashioned shot to the back of the head — bada-bing, bada-boom — would have sufficed. But no, the old bosses are vengeful, coldhearted pricks, and the shock here is the ghastly lengths they go to torture and make an example of Nicky. After leveling Nicky with an aluminum bat, Marino, Nicky’s former #2, and crew use his kid brother, Dominick, for batting practice. Not only is Nicky forced to watch his brother bloodied and beaten within an inch of his life, stripped, and rolled into a grave, he’s getting a preview of his own fate. In the end, the siblings are buried alive in that cornfield. Nicky never lives to tell the tales of his glory years in Vegas. Though, oddly enough, he still gets to narrate them. –Matt Melis
07. Call It
No Country for Old Men (2007)
Hit Man: Anton Chigurh
Who Got Whacked? Carla Jean Moss
What’s most startling about this hit is that it’s essentially self-imposed. Nobody cares if Carla Jean Moss (Kelly Macdonald) dies. “I ain’t got the money. What little I had is long gone, and there’s bills aplenty to pay yet. I buried my mother today. Can’t pay for that neither,” she explains to the Walking Death that is Anton Chigurh (Javier Bardem). Problem is this unstoppable killing machine can’t shake his clear cut principles, an attribute that leads rival bounty hunter Carson Wells (Woody Harrelson) to ask: “Do you have any idea how crazy you are?” Before he’s shot to hell, that is. Yet it’s an intriguing question that understandably confuses Chigurh simply because that is all he knows. He has his code and that code is who he is. Which is why he makes good on his threat to Llewelyn Moss (Josh Brolin) that he would kill his wife, even long after the deal has been settled. So, I ask you, what’s the most you ever lost on a coin toss? –Michael Roffman
06. What Does Marsellus Wallace Look Like?
Pulp Fiction (1994)
Hit Men: Jules Winnfield and Vincent Vega
Who Got Whacked? Brett, “Flock of Seagulls,” and Marvin (accidentally)
Jules (Samuel L. Jackson) and Vincent (John Travolta) are hit men. We figure this out only a few minutes and a debate about foot massages into Quentin Tarantino’s Pulp Fiction. But by 1994, hit men had come a long way from the old days of “If I wanted to kill you, you’d be dead already.” Not only does being on Jules’ shitlist mean “your ass,” it also means having him eat your Big Kahuna burger, drink your Sprite, play a game of 20 Questions with you, kill your friend in front of you, shoot you in the arm while you answer his questions, and quote scripture to you right before he finally riddles you with bullets. (Fuck, who has the time to be whacked these days? I know I don’t. I have shit to do.) And while our eyes bug out as we watch and listen to this incredibly drawn-out slaying ritual, Vincent all but yawns in the background. Clearly, he’s heard Jules’ little spiel countless times before. Oh, well. One film writer’s sixth most shocking mob hit of all time is just another ho-hum day at the office for these 9-to-5 gangsters. –Matt Melis
05. My Brother’s Keeper
The Godfather: Part II (1974)
Hit Man: Al Neri
Who Got Whacked? Fredo Corleone
Nothing that happened over the previous seven years since Michael (Al Pacino) settled all affairs in New York, moved his family to Las Vegas, and began building the Corleones into the most powerful crime organization in the country suggests that he is incapable of killing his brother. We want to believe he actually forgives Fredo (John Cazale) at their mother’s funeral at his sister Connie’s (Talia Shire) behest, but as he embraces his brother for the first time since disowning him, we see the cold, telling look he gives Al Neri — Fredo is done for. Even as Connie cancels Anthony and Uncle Fredo’s fishing trip, which sends the doomed brother out on the boat alone with Neri, the menacing score seeps in, and we have flashbacks to how Michael ties up loose ends in The Godfather, we still want to believe that the calculating, callous mob boss that Michael has become will show mercy to his own brother, whose crime wasn’t betrayal but stupidity. Each time I watch Fredo saying that Hail Mary on the boat, part of me thinks this will be the time that his prayers get answered. Michael’s decision, while a powerful message to both friends and enemies, goes on to haunt him in The Godfather: Part III as the one sin he can never fully atone for. –Matt Melis
04. Here’s Shooting at You, Kid
Angels with Dirty Faces (1938)
Hit Man: Rocky Sullivan
Who Got Whacked? Mac Keefer and Jim Frazier
You can’t have this list without James Cagney, the godfather of the “you dirty, yellow-bellied rat” era of gangster films. In Angels with Dirty Faces, Cagney plays Rocky Sullivan, a gangster who uncovers the shady dealings of crooked lawyer Jim Frazier (Humphrey Bogart) and corrupt contractor Mac Keefer. When the pair plot to kill Rocky’s boyhood friend, a priest who may blow their cover, Rocky has a little surprise for them: lead poisoning, see. While this two-for-one special might seem tame by today’s standards, I can only imagine what it was like to see and hear Cagney guns ablaze back in ’38 with the crack of gunfire, a sneer, and lines like, “Morning, gentlemen. Nice day for moida.” Now this is why the talkies were invented! –Matt Melis
03. Breakfast of Champions
American Gangster (2007)
Hit Man: Frank Lucas
Who Got Whacked? Tango
“You are who you are in this world. You’re either somebody, or you’re nobody.” What makes Frank Lucas (Denzel Washington) so endearing and triumphant is how he works strictly off logic. Bullshit doesn’t fly in his book and he always plays it cool. Which is why his early merciless hit on Tango (Idris Elba) encapsulates his entire personality. Frank’s reasoning is simple: He’s owed money, the guy’s playing him for an idiot, and so pop goes the weasel. The way he drops a jar next to Tango’s head and pays him his 20% before he walks off only speaks further to his strict and severe constitution. What’s shocking is how Frank never hesitates, not even for a second, despite being surrounded by dozens of morning commuters and onlookers. It’s a level of comfortability that few gangsters ever exhibit on film, and one that Washington relishes. The sweet cherry on top is how Frank walks back and finishes his breakfast. What a hero. –Michael Roffman
02. Dinner at Mrs. DeVito’s
Hit Men: Tommy DeVito and Jimmy Conway
Who Got Whacked? Billy Batts
That’s Billy Batts rattling around in the trunk of Henry’s (Ray Liotta) car at the beginning of Goodfellas. How’d he get there? Short story: he busted Tommy’s (Joe Pesci) balls. Long story: the night of agony that followed busting Tommy’s balls. When Tommy stumbles into Batts’ welcome-home party, Batts makes the mistake of reminding Tommy that he used to shine his shoes. Now, we all know that Tommy and his Napoleon complex can fly off the handle at any moment, but who would’ve thought that some dickish ribbing would lead to a long ride and a shallow grave? But the beating and killing aren’t really what’s so shocking here. It’s what happens in between. Tommy, Henry, and Jimmy (Robert DeNiro) drive to Tommy’s mother’s house to borrow a shovel. The sweet, old lady hears them come in, and we cut to the four of them around the dinner table eating, swapping jokes, and admiring the mother’s painting. (Tommy even borrows a butcher’s knife from her, which he later uses to stick Batts multiple times.) It would be a Norman Rockwell family dinner if not for the pounding coming from the trunk of Henry’s car right outside the dining room window. Pass the gravy, indeed. –Matt Melis
01. Highway to Hell
The Godfather (1972)
Hit Men: Seemingly every button man in the tri-state area
Who Got Whacked? Sonny Corleone
“This is the one that started it all.” A cliché, sure, but fitting given the circumstances of Sonny Corleone (James Caan) and the story of The Godfather. The eldest of Vito Corleone’s (Marlon Brando) four children, Sonny was the heir apparent, and his grizzly death here marks the ascent of his younger brother Michael (Al Pacino), who establishes the Corleones as the most powerful crime family in America. You know, after Mikey eviscerates the rival New York Dons and then sends Peter Clemenza (Richard S. Castellano) to catch Carlo Rizzi (Gianni Russo) by the neck with a wire. Still, even if Sonny’s fall has to happen for story’s sake, it doesn’t make the death any less shocking or tragic. He was simply under the impression that he had to save his kid sister — if only he had plowed through the Long Beach Causeway toll plaza. Stupid tolls. –Michael Roffman