Harry and Marv – Home Alone

Honestly, if the only obstacle between you and a big score is a prepubescent boy, and you’re still unable to finish the job, maybe it’s time to think of a new profession. This is doubly true for Harry and Marv, who were outsmarted by a pre-teen Kevin McCallister (Macaulay Culkin) not once, but twice. And something tells me their involvement with a child didn’t win them many friends in the big house.

Ken Pile – A Fish Called Wanda

When Ken Pile (right) is tasked with killing the only witness in a recent jewel heist, he ends up killing the target’s three dogs instead. Pile, an avid animal lover, is emotionally distraught by the killings. Luckily for him, the intended target ends up having a heart attack after witnessing the death of her pets, which means he was successful in his mission, albeit in a roundabout way.

H.I. McDunnough – Raising Arizona

There are probably better ways to meet a woman than repeatedly getting arrested. But that doesn’t stop H.I. McDunnough, who falls in love with the girl in charge of taking mugshot photos at the local jail. The two are later married, but it is soon discovered that his new bride is infertile. As a result, McDunnough decides to kidnap a child from local furniture baron Nathan Arizona, who was recently blessed with quintuplets. The resulting fiasco was not received well at the box office, but became a cult classic, and helped make a name for the Coen brothers.

Jerry Lundegaard – Fargo

Speaking of the Coen brothers, Fargo contains one of the most pathetic criminals in movie history. In an ill conceived plot to extort money from his father-in-law, Jerry Lundegaard hires a team of kidnappers to kidnap his own wife. Things quickly spiral out of control, and a mild mannered Jerry is ill equipped to deal with the situation.

Donnie Smith – Magnolia

I said Jerry Lundegaard might be the most pathetic character on this list. However, I must have forgotten about Donnie Smith (also played by William H. Macy). Smith is a down and out former child quiz-show contestant who is desperately in love with a young bartender with braces. In a bizarre attempt to win the young man’s affection, Smith gets braces of his own. The plan proves unsuccessful, and Smith is forced to steal from his former employer’s safe to pay off the procedure.

Tyrone, Sol, and Vincent – Snatch

If you’re going to point a gun, you’d better be ready to pull the trigger. Tyrone, Sol, and Vincent should have learned this lesson. In a pathetic attempt at robbery, the three use gun replicas to intimidate their victims. However, when their intended target recognizes the ruse, and pulls out his own .50 Desert Eagle, things quickly unravel.

Dignan – Bottle Rocket

Dignan thinks he has hatched the perfect robbery plan, and seeks the backing of a local underworld figure, Mr. Henry. However, Mr. Henry is simply using the the “robbery” as a diversion. While Dignan is busy robbing an empty safe, Mr. Henry is busy robbing Dignan’s house.

Ray – Small Time Crooks

In order to rob a nearby bank, Ray decides to rent a local business and tunnel in from the basement. As cover, Ray’s wife Frenchy starts selling homemade cookies from the storefront above. While Ray and his cronies are busy fumbling there way through an armature heist, Frenchy quickly turns the cookie business into one of the hottest spots in town. Of course, Ray is too busy trying to steal money to realize that his wife is making it hand over fist.

Sam and Eddie – Safe Men

Sam and Eddie are two second-rate lounge singers trying to make a buck. However, their passing resemblance to a pair of first-rate safe crackers draws attention from a local Jewish mobster, Big Fat Bernie Gayle. The two soon find themselves being pressed into service by the mob while at the same time being threatened by their real criminal counterparts.