Plethora of Mistakes

""Fucked it up. The whole plan was fucked up. We ain't do shit right out there, man. Shit"."

- Curtis, Dead Presidents.

Similar to A Simple Plan, but applied to crime dramas, thrillers, etc.. Basically, it's either a very simple plan or a very complicated plan where EVERYTHING goes wrong for the sake of going wrong. This is usually an Anvilicious way of saying crime doesn't pay.

For example, a criminal (or a group of criminals) has an elaborate masterful plan to rob a bank, or perhaps murder someone, or whatever. But that's a lot easier said than done, isn't it? Soon cracks start to show after the plan goes through, or during the execution of said plans, likely in the form of loose ends. Everything starts to unravel when the Plethora of Mistakes are shown. Somebody forgot to disable the security camera, or someone left behind a crucial piece of damning evidence for Inspector Javert. Or maybe one of the group members was a loose cannon who lost his/her cool and killed someone, when the rules of the plan were "not to kill", as it would make things more complicated. Or maybe, during the bank heist, somebody got greedy and started to take more than what they could carry, thus going over the pre-established time limit. Or someone is starting to crack under pressure. Either way, the person or party involved has to fix the mistakes, which usually causes even MORE mistakes.

The bane of Stupid Crooks everywhere. Sometimes overlaps with Diabolus Ex Machina.

Tropes that leads to this one

 * Can't Get Away With Nuthin': likely plays a HUGE part in this trope as well. Very rarely do criminals get away with their plans in mainstream media.
 * Guilt Ridden Accomplice: Exactly What It Says On the Tin, someone whom feels guilty over their crime. Expect these people to undermine and sabotage the heist out of guilt or remorse.
 * Psycho Party Member: A accomplice who's a loose canon, who can't stick to the plan. Or alternatively some one whom was otherwise normal that lost their marbles due to the pressure.
 * Stupid Crooks: Sometimes the criminal(s) just aren't very smart. Although they can be very smart and calculating and still have this trope happen to them.
 * Tragic Mistake: If it's from the criminal's POV expect to see a bunch of Tragic Mistakes.

Anime & Manga

 * Kira comes dangerously close to this in Death Note. Especially with the loose end Naomi Misora.

Film

 * Very Bad Things starts with a Bachelor Party on that's dirtier than their wives/fiances want. Then, while high on cocaine, the hooker they hired is killed when her head is impaled during sex. Hiding the body ends up making things worse and that's when Murder Is the Best Solution comes up... Again and Again...
 * Several movies by the Coen Brothers feature seemingly simple plots gone horribly wrong.
 * Fargo
 * Raising Arizona
 * Blood Simple
 * The Lady Killers (The heist itself goes off without a hitch, it's dealing with the sweet old lady who witnessed it that's problematic)
 * Burn After Reading
 * No Country for Old Men. Boy howdy!
 * The Big Lebowski by contrast, has a number of complicated plots gone horribly wrong, mainly by crashing into each other.
 * Reservoir Dogs. The heist goes to hell due to one of the crew going psycho and shooting up the joint upon the alarm being sounded, and the cops showing up much earlier than they were supposed to due to . And then things get worse.
 * The Liars Club (an obscure teen thriller)
 * Before the Devil Knows You're Dead: Almost to the point of parody. It makes Reservoir Dogs look like Heat.
 * Stag (similar to Very Bad Things, but came out before it)
 * Somewhat subverted in the Denzell Washington film Out Of Time, as the protagonist was able to narrowly intercept and fix the mistakes before they got worse.
 * A Fish Called Wanda.
 * The bank heist in the film Dead Presidents
 * Snatch. Let's just say getting a diamond onto an aeroplane is not nearly so simple as it seems. Neither is understanding Brad Pitt.
 * A Perfect Murder plays with this.
 * Bound. On both sides of the scam.
 * The Next Three Days plays with this a little.
 * Valkyrie
 * Armored is of the Guilt Ridden Accomplice flavor.
 * The Asphalt Jungle turns into one of these due mostly to emotional misjudgements and plain, simple bad luck.

Literature

 * The misleadingly titled book and movie A Simple Plan.
 * The book (and less so, the movie) The Hot Rock. The "simple" crime of stealing a diamond becomes a series of crimes as things keep going wrong. As one character says, "I've heard of the habitual criminal but never the habitual crime".
 * This is a recurring theme in the John Dortmunder novels by Donald Westlake (of which The Hot Rock is the first). Dortmunder is a spectacularly unlucky criminal. The other novels (some of which have been filmed) are: Bank Shot, Jimmy the Kid, Nobody's Perfect, Why Me?, Good Behaviour, Drowned Hopes, Don't Ask, What's the Worst That Could Happen?, Bad News, The Road to Ruin, Thieves' Dozen, Watch Your Back, What's So Funny?, and the novella Walking Around Money.
 * One Fine Day in The Middle of The Night

Live Action TV

 * On Prison Break this happens to Michael's well thought out plans....A LOT. Almost to the point of being a Diabolus Ex Machina.
 * On Luther, this happened to in the fifth episode of series 1. His plan to get hold of some diamonds goes horribly wrong, leading to several unnecessary deaths, and his attempts to fix the mistakes leads to  And trying to fix this ends with.

Tabletop Games

 * Fiasco ("a game of powerful ambition and poor impulse control") is specifically described as "like making your own Coen Brothers movie", and cites several of their films listed above as inspiration.

Video Games

 * Happens a lot in the Grand Theft Auto series.
 * Niko Bellic Lampshades this in GTA IV, sarcastically saying he hopes attack helicopters and submarines don't show up during a mission.