Hollywood’s 25 Most Hilariously Inept Crooks

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?

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.

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.

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.

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.

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.

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.

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.

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.

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’s 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.

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.

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.

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.

“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 accidentally takes rat poison thinking it’s medicine.

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.

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.

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.

“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.

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.

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.

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.

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.

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.

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 shoots him dead.

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.