The Clumsiest Criminals in Film History

The Clumsiest Criminals in Film History

A clever, devious movie villain can somehow pull off the most ingenious robberies or diabolical murders. Although such villains almost always pay for their crimes, they show us plenty of skill and intelligence along the way and sometimes even earn our grudging admiration. (These are the 50 most popular villains of all time.)

Well, most movie villains, anyway. Some, on the other hand are, well, dumb. They conjure up grand criminal plots, but fail at the execution. They don’t consider every contingency or they just have bad luck. When things go wrong, they panic, make wrong decisions, and often double-cross their partners. They’re bumblers. 

 To identify the most bumbling criminals in film history, 24/7 Tempo reviewed plot summaries from IMDb, an online movie and TV database owned by Amazon, and other sources in the U.S. and U.K.

Some of the criminals on our list are good people at heart who stumble into crime with no idea what they’re doing. Others are evil and get done in by their own greed.

 Often, it’s rotten luck or bad timing that foils their plots. In “The Godfather II,” Carmine and Tony Rosato’s plan to kill a rival mobster in broad daylight at a bar is interrupted when a police officer walks in. Luckless Joe “Mental” Mentalino of “Dumb & Dumber” accidently poisons himself with what he thinks is his ulcer medication. The bank robbers in “Quick Change” get robbed themselves when they get lost in Brooklyn on the way to the airport.

Other miscreants underestimate their intended victims – like Jasper and Horace from “101 Dalmatians,” who are outwitted by man’s best friend, or Harry and Marv from “Home Alone,” tormented by the young boy whose house they’re trying to rob.

Some bumbling criminals are characters in serious films and come to truly tragic ends. Happily, though, many of them are in comedies, so we get to laugh at their expense. (Here’s a list of the funniest American movies of all time.)

Source: Michael Ochs Archives / Getty Images

Carmine and Tony Rosato from “The Godfather II” (1974)
> Portrayed by: Carmine Caridi and Danny Aiello

Low-level hoodlums Carmine and Tony Rosato cook up a plan to kill rival mobster, Frank Pentangeli. During a sit down between Carmine and Pentangeli at a bar, Tony Rosato starts to garrote Pentangeli and yells, “Michael Corleone says hello!” But the murder is interrupted when a bet cop, drawn by Pentangeli’s cries, enters the bar and a shootout ensues. Maybe killing someone in a bar during the day wasn’t the best idea?

Source: Courtesy of Focus Features

Chad Feldheimer and Linda Litzke from “Burn After Reading” (2008)
> Portrayed by: Brad Pitt and Frances McDormand

Personal trainer Chad Feldheimer thinks he’s found a goldmine in a memoir written by a CIA agent. He and a co-worker, Linda Litzke, decide to sell what they think is secret government info to the Russians. In an effort to get more information, Linda and Chad break into the home of the CIA agent, but Chad is shot dead by Linda’s secret lover.

Source: Courtesy of Twentieth Century Fox

Chazz, Pip, Rex from “Airheads” (1994)
> Portrayed by: Brendan Fraser, Adam Sandler, Steve Buscemi

Chazz, Rex, and Pip play in a Los Angeles hard rock band called “The Lone Rangers.” A misguided attempt to get the band’s demo tape played at a local rock station ends up with the tape destroyed and the station being surrounded by a SWAT team after Chazz pulls out a water pistol filled with hot sauce. In the end the band members are seen playing a concert in prison after being charged with kidnapping, theft, and assault with hot sauce – but their album, “Live in Prison,” goes triple platinum.

Source: Courtesy of Warner Bros.

Clarence Worley from “True Romance” (1993)
> Portrayed by: Christian Slater

Some crooks are just plain lucky. Elvis Presley fanatic Clarence Worley kills his girlfriend’s pimp. After the murder, Alabama, now his wife, and Clarence flee with the pimp’s cocaine haul. In Los Angeles, the couple tries to sell the cocaine but cops and gangsters ambush the deal. Clarence and Alabama escape a shootout and flee to Mexico with the money from the cocaine sale.

Source: Courtesy of Warner Bros.

David Clark from “We’re the Millers” (2013)
> Portrayed by: Jason Sudeikis

Small-time marijuana dealer David Clark brings together a fake family, the Millers, to smuggle drugs across the border to Mexico to pay off a debt to his drug supplier. Along the way, the family’s RV goes off the road and one of the family members is hospitalized. Clark tries to abandon his newfound family, but the group stays together in the witness protection program after the drug deal goes down.

Source: Courtesy of Sony Pictures Releasing

Dignan from “Bottle Rocket” (1996)
> Portrayed by: Owen Wilson

Dignan’s problem is he thinks of grand criminal schemes, but can’t quite pull them off. Dignan helps his friend, Anthony, escape from a psychiatric unit where he is staying voluntarily. The two decide to go on a crime spree, but Dignan ends up in jail in the end.

Source: Courtesy of New Line Cinema

Dr. Evil from “Austin Powers: International Man of Mystery” (1997)
> Portrayed by: Mike Myers

A parody of a James Bond villain, Dr. Evil plots to take over the world after being frozen cryogenically for 30 years. Like all Bond villains, he’s foiled by a suave English spy – in this case, Austin Powers. His schemes, like blowing up the ozone layer, have already been tried, so he plans to hold the world hostage for $1 million (later raised to $100 million) with a warhead from a breakaway Russian republic. Powers gets wind of his plan and deactivates the warhead.

Source: Courtesy of Buena Vista Distribution Company

Earl from “Ruthless People” (1986)
> Portrayed by: Bill Pullman

Kidnappers grab the wife of Sam, a Beverly Hills fashion tycoon, but he’d planned to kill her anyway and doesn’t want her back. Earl, the boyfriend of Sam’s mistress, gets involved in the plot, and films what he thinks is Sam disposing of his wife’s body – but it’s not. Sam ends up deciding to pay the ransom, and Earl tries to steal it, but gets arrested.

Source: Courtesy of Warner Bros.

Grimm, Loomis, Phyllis from “Quick Change” (1990)
> Portrayed by: Bill Murray, Randy Quaid, and Geena Davis

Dressed as a clown, Grimm robs a bank, getting away with $1 million with his girlfriend Phyllis and friend Loomis. Although the robbery goes off as planned, their escape does not, as the trio tries to leave New York City and gets lost in Brooklyn, robbed, and nearly shot. Eventually, they successfully flee the country on a plane.

Source: Courtesy of Twentieth Century Fox

H.I. McDonough from “Raising Arizona” (1987)
> Portrayed by: Nicolas Cage

Convenience store robber H.I. “Hi” McDunnough and his wife, police officer Edwina, kidnap a baby. The baby is subsequently kidnapped by another man and then a pair of ex-convicts. When Hi and Edwina rescue the baby and try to give him to his real father, the father lets them keep him, as he was one of quintuplet sons. Along the way, HI kills a biker who was beating him by pulling the pin of a grenade in the biker’s jacket. The kidnapped baby grows up to become a football star and Hi and Edwina are seen surrounded by children and grandchildren at the end of the film.

Source: Courtesy of Twentieth Century Fox

Harry and Marv from “Home Alone” (1990)
> Portrayed by: Joe Pesci and Daniel Stern

Thieves Harry and Marv plan to break into a house over Christmas. A young boy, Kevin, was accidentally left home alone by his family when they left on vacation. As Harry and Marv try to break in, Kevin thwarts them with a series of clever and painful traps. The thieves are arrested and Kevin is reunited with his family.

Source: Courtesy of Buena Vista Distribution Company

Jasper and Horace from “101 Dalmatians” (1961)
> Portrayed by: J. Pat O’Malley and Frederick Worlock (voices)

Villainess Cruella de Vil hires Jasper and Horace Baddum to kidnap a bunch of Dalmatian puppies for their fur. But the dogs rally and outsmart the would-be kidnappers. The puppies are returned to their humans.

Source: Courtesy of Gramercy Pictures

Jerry Lundegaard from “Fargo” (1996)
> Portrayed by: William H. Macy

Car salesman Jerry Lundegaard wants money from his wealthy father-in-law, so he hires two henchmen to kidnap his wife. But the father-in-law is killed when he refuses to hand over the ransom. A smart police detective trails Jerry, and in the end he’s arrested for his role in the plot.

Source: Courtesy of New Line Cinema

Joe Mentalino from “Dumb & Dumber” (1994)
> Portrayed by: Mike Starr

“Dumb & Dumber” follows two clueless friends as they try to return a briefcase full of money – which they don’t realize was a ransom payoff. The kidnapper, Joe “Mental” Mentalino, chases the two friends cross-country to retrieve the cash. Unfortunately, Mental never gets the money after he accidently takes rat poison thinking it’s medicine.

Source: Courtesy of Twentieth Century Fox

Johnny Dangerously from “Johnny Dangerously” (1984)
> Portrayed by: Michael Keaton

Good guy Johnny Kelly, aka Johnny Dangerously, enters a life of crime to pay his mother’s medical bills and send his brother, Tommy, to law school. In this parody of 1930s gangster movies, Johnny escapes Death Row after he’s framed for a murder he didn’t commit and is eventually pardoned by the governor.

Source: Courtesy of Metro-Goldwyn-Mayer

Ken Pile from “A Fish Called Wanda” (1988)
> Portrayed by: Michael Palin

Ken Pile teams up with his gangster partner, George, and two American con artists to steal a cache of diamonds. Like all partners in crime, they all end up betraying each other and only Ken knows how to access the diamonds hidden in a safe deposit box. Ken, an animal lover, tries to kill the only witness to the crime, but accidentally kills her dogs and the woman dies of a heart attack. Trying to get him to reveal where the diamonds are, one of the Americans eats Ken’s pet fish.

Source: Courtesy of Embassy Pictures

Leo, Max from “The Producers” (1967)
> Portrayed by: Gene Wilder, Zero Mostel

Corrupt Broadway producer Max Bialystock convinces skittish accountant Leo Bloom to participate in his scheme to finance a flop. By duping investors, a flop could make more money, Max says. But to their surprise their musical, “Springtime for Hitler,” turns out to be a hit, and the fraudsters end up in jail.

Source: Courtesy of Continental Distributing

Professor Marcus from “The Ladykillers” (1955)
> Portrayed by: Alec Guinness

“Professor Marcus” and his team of criminals pretend to be musicians as they rent rooms from an eccentric old lady Mrs. Wilberforce. But they’re really planning a heist. After robbing a van, the Professor and his partners have Mrs. W. retrieve the money. She is unaware the loot is from a robbery. When she catches wind of their plan, Mrs. W. tells them she will go to the police. The criminals decide to kill her, but they are anything but “lady killers” as they end up killing each other instead.

Source: Courtesy of DreamWorks Distribution

Ray Winkler from “Small Time Crooks” (2000)
> Portrayed by: Woody Allen

Small time crook Ray Winkler wants to rent a pizzeria so he and his team can tunnel under it to a nearby bank. The robbery fails, but Ray’s wife, Frenchy, opens a cookie business in the building and makes millions. Ray and Frenchy split, and Ray tries to steal a valuable necklace at a party by making a duplicate. Ray gets the real and fake necklace mixed up and gives the fake one to Frenchy when he tries to reconcile with her. All ends well as the two end up together after all.

Source: Courtesy of Twentieth Century Fox

Robert Lewis from “A Life Less Ordinary” (1997)
> Portrayed by: Ewan McGregor

When janitor Robert is fired by his company, he kidnaps the boss’s daughter, a spoiled 20-something named Celine. A busted bank robbery and much bickering between Robert and Celine ensue before the two realize they’re in love.

Source: Courtesy of Sony Pictures Entertainment

Sol, Tyrone, Vinny from “Snatch” (2000)
> Portrayed by: Lennie James, Ade, Robbie Gee

Sol, Tyrone, and Vinny are minor players in a diamond heist. Though they have the diamond in their possession at one time in this rather complex plot, Tony ends up dead, and Sol and Vinny are arrested.

Source: Courtesy of Warner Bros.

Sonny and Sal from “Dog Day Afternoon” (1975)
> Portrayed by: Al Pacino and John Cazale

Sonny and his partner Sal attempt to rob a bank in Brooklyn, but find the bank only has $1,100 in cash because the money has already been picked up for the day. After taking the bank employees hostage, Sonny yells “Attica, Attica!” after police surround the bank. Sonny ends up in prison after trying to escape and Sal is shot in the head.

Source: Courtesy of Warner Bros.

Stacks Edwards from “Goodfellas” (1990)
> Portrayed by: Samuel L. Jackson

Stacks Edwards had one job – get rid of the van a group of mobsters led by Henry Hill and Jimmy Conway used in the heist of Lufthansa airlines at what is now JFK Airport. He didn’t, and left the van for the police to find. Jimmy then has Stacks, among others involved in the plot, killed.

Source: Courtesy of Miramax

Vincent Vega from “Pulp Fiction” (1994)
> Portrayed by: John Travolta

Sometimes nature calls at the most inopportune times. Hitman Vincent Vega is sent to kill a boxer, Butch, who double-crossed Vega’s boss, Marsellus. But when Vega arrives at the boxer’s apartment, Vincent is on the toilet and the boxer shots him dead.

Source: Courtesy of Cinerama Releasing Corporation

Virgil Starkwell from “Take the Money and Run” (1969)
> Portrayed by: Woody Allen

Virgil Starkwell wasn’t cut out for a life of crime. During a bank robbery, he argues with the cashier about the handwriting on the demand note. Caught and imprisoned, he tries to escape with a gun made out of soap, but fails when the “gun” melts in the rain. He does eventually escape, but is the only inmate to do so after a mass escape was called off. Virgil is again imprisoned and seen once again sculpting a gun from soap and asking if it happens to be raining.

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