10 hitmen in film who are really bad at their jobs

These "professionals" couldn't shoot their way out of a paper bag

By Jen Lennon, Jim Vorel  |  June 8, 2024 | 1:00pm
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10 hitmen in film who are really bad at their jobs
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Glen Powell as Gary Johnson in Hit Man Image: Brian Roedel/Netflix

Hitmen are an essential part of the action thriller formula: Good guy tries to stop bad guy, bad guy puts out a hit on good guy, good guy dispatches the goon(s) before the final confrontation with bad guy. That’s the plot of basically every James Bond movie, right? Occasionally, you get a play on that formula where the assassin is the protagonist, like in John Wick. But for the most part, assassins in film are portrayed as serious, competent people of whom you should actually be afraid.

But not everyone is always suited for the work they do. Sometimes, people are just bad at their jobs, and hitmen are no exception. You’d think that there would be a basic degree of competence required when dealing with a job that has such high stakes, but, as these characters demonstrate, you’d be wrong. Whether they’re taking out the wrong targets, shooting people accidentally, or just not thinking about the consequences of their actions, these profoundly unserious hitmen defy the silent, deadly killer trope. To celebrate the release of Richard Linklater’s Hit Man—which offers a unique take on why Glen Powell’s Gary Johnson is not a good killer—we’ve rounded up nine hitmen, or hitman teams, in film that buck the stereotype. We also tossed in a bonus pick from The Simpsons, because it was simply too good not to include.

Vincent Vega - Pulp Fiction
I Shot Marvin in the Face - Pulp Fiction (11/12) Movie CLIP (1994) HD

Getting shot just as you’re leaving the bathroom is an undignified way to die in general, but it stings a lot more when you’re supposed to be a professional hitman. Based on Vincent Vega’s (John Travolta) actions throughout Pulp Fiction, it’s a wonder he made it that far in his career at all.Throughout the film, Vincent is oddly careless about gun safety. He shoots Marvin in the face by accident, which should be enough to get him booted from the Professional Assassins Guild or whatever other organizing body takes care of workplace safety complaints and HR issues for contract killers. When you’re that sloppy, you make the whole profession look bad. It’s not much of a surprise that his carelessness—he left his gun just sitting on a counter while he went to use the bathroom, giving Butch the opportunity to take it and shoot him—is what gets him killed in the end. [Jen Lennon]

Ray - In Bruges
In Bruges (2008) - You Were Gonna Kill Me Scene (5/10) | Movieclips

Some people just aren’t cut out for the hitman life, and Ray (Colin Farrell) is one of them. He fucked up his very first job, and he fucked it up bad—he was supposed to kill a priest, but he ended up killing a child, too. That, according to his boss, Harry (Ralph Fiennes), is unforgivable. But Ray can’t live with the guilt, either. Ray tries to kill himself; Harry tries to have him killed. None of it sticks. You almost feel bad for Ray until you remember—oh wait, this guy is a hitman, and he couldn’t even do his job correctly. [Jen Lennon]

Gary Johnson - Hit Man
Hit Man | Official Trailer | Netflix

Gary Johnson (Glen Powell) isn’t quite like the other hitmen on this list; he’s not actually a hitman at all. He’s a college professor working undercover for the police, setting up sting operations where he just pretends to be a hitman in order to entrap would-be criminals. It’s a fun set-up for a movie, but if you’re not planning to follow through on the work you’ve been contracted to do, you’re probably not very good at your job. [Jen Lennon]

Joe Mentalino - Dumb And Dumber
Dumb & Dumber | Harry & Lloyd Pick Up a Hitchhiker | HBO Max

Look, it’s easy enough to understand, if not exactly condone, the desire of “Mental” to immediately rub out Lloyd Christmas and Harry Dunne when he’s picked up by them as a hitchhiker in the course of their cross-country journey to Aspen. There are few fates on Earth more top-of-the-charts irritating than being sandwiched between this pair in a dog-shaped truck hurtling down the interstate, while they bicker or bellow their version of “Mockingbird” directly into your ears. It would take inhuman patience just to endure being in their company for more than a couple of minutes.But still, even after uncovering that these two are just a pair of rubes, Mental really should have showed a bit more due diligence regarding the best practices of professional hitmen. We’re talking about rules like: Hey, don’t leave your food unattended with the people you’re planning to assassinate. It’s that little lapse that costs Mental his life, when the hapless pair unknowingly exploits his ulcer with hot peppers and then shoves a handful of rat poison down his throat. A consummate professional would have known better than to let his guard down, even when dealing with a pair of idiots. Mental quickly pays the price for his carelessness. [Jim Vorel]

Gaear Grimsrud - Fargo
Fargo (1996) - Whoa Daddy Scene (6/12) | Movieclips

Gaear Grimsrud (Peter Stormare) is actually a hell of a lot more ruthlessly professional than his partner, Carl Showalter (Steve Buscemi). When you’ve got a kidnapped woman in the trunk of your car and a suspicious police officer standing at your car window, you need to assuage that cop’s worries and get them to move on without incident. Carl fails spectacularly at this mission, trying to bribe the trooper with a paltry $50. That only makes the cop more suspicious, and, by this point, Gaear has had enough of Carl’s incompetence and quickly and efficiently shoots the officer right there on the side of the road.You can’t really blame Gaear for getting fed up with Carl’s bumbling buffoonery, but his rash action causes a chain reaction: Two passersby witness the incident, so Gaear has to kill them, too, and suddenly Gaear and Carl’s crimes have escalated from simple kidnapping to triple murder. Whoa daddy, indeed. [Jen Lennon]

Shawn, Derrick, and Shane - I, Tonya
Funniest scene in i, Tonya.

Derrick Smith (Anthony Reynolds) and Shane Stant (Ricky Russert) were never supposed to kill Nancy Kerrigan (Caitlin Carver), but they were trying to injure her, which they did by… hitting her in the knee with a baton. There are layers upon layers of incompetence here: Tonya Harding (Margot Robbie) and Jeff Gillooly (Sebastian Stan) told the FBI that they never intended to physically hurt Nancy—they just wanted to freak her out with a death threat. They lay the blame for the assault at the feet of Shawn Eckardt (Paul Walter Hauser), whom they hired to mail the threat. Shawn, in turn, hired Shane and Derrick to attack Nancy, because he thought that would bolster his “bodyguard” business that didn’t actually exist. That’s a stupid enough plan on its own, but when your own ceaseless bragging causes the FBI to arrest you because you just can’t stop telling people about what you did, that’s an all-time fuck-up. [Jen Lennon]

Tony and Joey - Midnight Run
Midnight Run | Jack Walsh and The Duke Escape the Mob

The particular indignity of these two clowns is that they work for a mob boss. They should, by all rights, be the best hitmen in the game. And yet. And yet. The Duke (Charles Grodin) slips through their fingers at every turn. The history of the mob is filled with legendarily competent hitmen: There’s Frank “The Irishman” Sheeran, who claims to have killed Teamsters leader Jimmy Hoffa, “Machine Gun” Jack McGurn, allegedly responsible for planning the 1929 St. Valentine’s Day Massacre, and the various criminals of Murder, Inc., a group of enforcers for the National Crime Syndicate. Tony (Richard Foronjy) and Joey (Robert Miranda) are fictional, but if they were real, they would be remembered with the same reverence as Richard “The Iceman” Kuklinski. Which is to say: they’d be laughed out of the room for even suggesting they were affiliated with the mob. After all, no one would believe that two mafia hitmen couldn’t manage to take out a simple accountant despite having multiple opportunities to do so. [Jen Lennon]

Dmitri Desgoffe-und-Taxis - The Grand Budapest Hotel
The Grand Budapest Hotel - Shootout Scene

In Dmitri’s defense, he’s not exactly what you would call a trained hitman. Indeed, he typically has no real need to be one himself, not when he employs the services of the genuinely terrifying J. G. Jopling (Willem Dafoe) to stalk and murder the family members of servants, or disapproving local lawyers. Suffice to say, he probably wasn’t expecting to get thrust into the role, but when Zero (Tony Revolori) manages to use the element of surprise to shove Jopling to his death from an icy cliff, Dmitri has no choice but to get his own hands dirty for once.And uh, it doesn’t go particularly well. Dmitri can cut a menacing figure when he’s stalking Agatha (Saoirse Ronan), but when the chips are down he simply reverts to grabbing for his ankle gun and firing in wildly ineffectual fashion, inadvertently kicking off a massive firefight between confused soldiers above the lobby of the titular hotel. As he might have put it himself, after negligently realizing that Boy With Apple was missing from his parlor after more than two weeks: “What’s the meaning of this shit?!?” [Jim Vorel]

Burke and Stokes - Death To Smoochy
Death to Smoochy - Chasing Burke

They got the wrong rhino. That’s the most distilled version of what happens when TV exec Marion Frank Stokes (Jon Stewart) and talent agent Burke Bennett (Danny DeVito) plot to kill children’s TV host Sheldon Mopes (Edward Norton), a.k.a Smoochy the Rhino. The people they hired were supposed to kill Smoochy; they killed Moochy (Michael Rispoli) instead. After that spectacular failure, they follow it up by hiring a children’s entertainer named Buggy Ding Dong (Vincent Schiavelli) to take out Smoochy. Clearly, Buggy Ding Dong will succeed where the other guys failed. Except, of course he botches it, because they entrusted a high-stakes job to someone who willingly goes by the name Buggy Ding Dong. Honestly, this one is on them. [Jen Lennon]

 
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