The most bumbling criminals in film history

Call them the Wet Bandits or the Sticky Bandits, Harry and Marv did have some success. Then, they ran into Kevin McAllister. Twice. Then, the duo suddenly turned into buffoons. Although, frankly, it’s impressive they both survived their run-ins with Kevin, who seems to have a sadistic streak in him.

Maybe it’s hard to find henchmen who are down to kidnap dogs just so you can make a coat. That’s the situation Cruella de Vil finds herself in. Her henchman, Jasper and Horace, aren’t the most effective in 101 Dalmatians, which is probably a good thing for kids watching the movie.

We will feature multiple Coen Brothers characters on this list because they specialize in bumbling criminals. Jerry Lundegaard probably thinks he’s smart. He cooked up a plan to have his wife kidnapped so he could get some of the ransom money from his father-in-law. However, he was so in over his head that, well, we end up with the plot of Fargo.

Kevin Kline won an Oscar for A Fish Called Wanda, and Otto isn’t exactly a smooth criminal. However, he rises above the level of incompetency. Ken, played by Michael Palin, is a little more of a bumbler. After all, he managed to accidentally kill three different dogs on three separate occasions.

In Wes Anderson’s breakout film Bottle Rocket , Dignan is all in on becoming a criminal mastermind. He just doesn’t have the chops for it. Played by an unknown Owen Wilson, Dignan is an underrated character in the Anderson canon.

Nicky was quite successful for a while. He was arguably the world’s greatest cat burglar. On the other hand, the Muppets were able to catch him. If a group that includes Fozzie stops you, you can’t be all that good, right? Then again, maybe Nicky’s mind was clouded with love for Miss Piggy.

Johnny Dangerously is a crime comedy, so naturally, there are some goof-ups and less-than-successful criminals. The titular character, played by Michael Keaton, is a bit of a smooth customer. That’s not as true of his rival Danny Vermin, played by Joe Piscopo in a very ‘80s casting choice.

No, not Morgan Freeman’s character from Shawshank Redemption . We’re talking about the mononymous character played by Danny McBride in Pineapple Express. Saul may be kind of dumb, but he’s a successful marijuana dealer. On the other hand, Red falls short more often and is a bit of a doofus.

Look, Joe couldn’t catch Harry and Lloyd in Dumb & Dumber. Then, he is accidentally killed by the dumb duo. How could you be considered anything but a failed criminal if that’s your ultimate fate?

The Informant! is an underrated movie based on a true story. Matt Damon plays Marc Whitacre, who starts as a whistleblower. All the while, he was committing embezzlement. Whitacre is bipolar, which undoubtedly influenced his erratic behavior and questionable decisions. He also got caught, and his exploits played a part in that.

He struggles to ask for the right amount of money. His goons all seem unqualified. He can’t manage to kill Austin Powers or even his own son. No, Dr. Evil is not all that successful. After all, he’s basically a parody of all those Bond villains who fall short. He just takes it to a bigger, more comedic level.

We’re talking about a character played by Leslie Nielsen well after he stopped playing it straight, so obviously, he’s quite bumbling. The Naked Gun star has the role of the villainous Colonel Chi in the forgotten ’90s film Surf Ninjas. Rob Schneider plays one of the guys who stop him. Need we say more?

Another Coen Brothers character, this one from Burn After Reading. This dark comedy involves a lot of criminal types making mistakes. However, airhead Chad takes the cake in terms of incompetence. Brad Pitt seems to be having a lot of fun as the character, though Chad has a lot less fun.

Speaking of Naked Gun, Ruthless People is directed by the same trio as Airplane! and those other spoof comedies, though it’s not a spoof film. Earl is the dumbest of the bunch, and not only that, he’s played by Bill Pullman in his film debut.

Small Time Crooks is a farce entirely about bumbling criminals. While the movie isn’t entirely successful, it has its moments, and the main characters are failures as criminals. We figured it should be included, and Ray is the main character. Also, he’s played by Woody Allen, so this movie likely will be forgotten soon enough.

In Quick Change, Bill Murray and Geena Davis’ characters seem like they are on the ball. It’s the city of New York and the people they run into that are keeping them from making their getaway after a successful robbery. Also, the third team member, Loomis, is posing a problem. Played by Randy Quaid, he makes some questionable decisions.

Mafia! wants to be Airplane! but for mob movies. It doesn’t reach that level of success. However, it’s a slapstick comedy about criminals. It’s loaded with bumbling crooks. Vincenzo is in the Marlon Brando role, though, and he’s played by Airplane! alum Lloyd Bridges. That’s why we shouted him out.

We’re the Millers is about a weed dealer who hires a stripper and two teenage delinquents to pose as his family so he can transport a big marijuana score. That dealer is David Clark. The entire hook of the movie is incumbent on David not being particularly bright or criminally astute, so he makes the cut.

Before he was a movie star, Adam Sandler was one of the members of the band The Lone Rangers in Airheads . Along with Brendan Fraser and Steve Buscemi, the band decides to hold a radio station hostage to try and get their demo played. If that decision seems questionable, you aren’t the only one who thinks that.

We had to end with one more character from the patron saints of bumbling criminals, Joel and Ethan Coen. Their breakout film, Raising Arizona , features such a character. That’s H.I., played memorably by Nicolas Cage. He’s a recidivist criminal and lowlife when the film begins until he becomes a family man. By kidnapping a baby so he and his wife can finally have a kid, it should be said.