- A frustrated, unemployed professor joins forces with a scammer and a friend of his in a blackmailing scheme.
- Charlie is an ex-professor turned reluctant call-center employee who gets fired on the first day. Distraught at being unable to provide for his daughter Emily and wife Penelope, he accepts when aspiring scam artist Gus presents Charlie with a seemingly snag-free plan to make some cash. The plan is to blackmail Reverend Smalls, a man of the cloth who's frequently turned up in the company database of visitors to illegal porn sites. Gus plans to extort Reverend Smalls, with the intention of publicly exposing his secret shame should he refuse, thus potentially destroying the man's career. Normally cautious, Charlie is keen on participating in this scam, confident that the money he'll make from the scam will finally help turn things around for him and his family. The plan goes ahead when they are joined by Gus' ex, one-time pageant queen Josie McBroom, but it goes wrong when Reverend Smalls dies thanks to this trio, and this is only the start of their troubles.—????
- A simple plan, so long as everyone sticks to it! Blackmail the local preacher. Hide the money, get your alibi straight, wait for 24 hours and then run.... Right. So Charlie (David Schwimmer), with a family to support goes along with Gus's (Simon Pegg) "simple" plan to net them enough cash to vanish on. But then Josie (Alice Eve) appears and gets herself in on the deal. They do the deed, and Josie cuts the deal with the local preacher. On schedule, Gus goes to collect the money. So far so good.
Gus's alibi, to be set up by Charlie, isn't where he's supposed to be, however, and so Charlie panics, just as Gus is being held at gunpoint by the Reverend. Shots are fired. Charlie races to find Gus, but finds a body in a pool of blood instead. He panics and (weighted with a garden gnome) drops the body in the septic tank. Gus reappears, cleaning the gunshot wound to his leg. Turns out, Charlie just drowned the unconscious Rev!
Deputy Garman (William Rosenfeld a.k.a. Billy Asher) comes knocking on the Reverend's door just as Gus and Charlie discover the snuff movies the Rev has been producing. The deputy informs Charlie, who he assumes lives in the house, that the Reverend's body has just been found in a car down the road. In his surprise at finding out that the person he accidentally killed wasn't the reverend after all, Charlie acts suspiciously enough to invoke the Deputy's detective skills. Desperate to get rid of him, Gus knocks him out with an ornament, and they tie him up. The door opens and the Reverend's wife Mrs. Smalls (Mimi Rogers) enters, confessing to having murdered her husband whom she calls a pervert. She's looking for her partner who is due to arrive and run away with her and the $2 million they have in a bag, revealing the identity of the man that just drowned in the septic tank.
Just when Mrs. Smalls is about to shoot Deputy Garman, Josie comes to the rescue and plants an axe in Mrs Rev.'s head. Three dead, a police deputy for a hostage and a bag of money, the trio figure that it's time to get away. The deputy, heavily intoxicated thanks to Josie's plan to make him appear guilty, tries escaping through the bathroom window and cracks his skull open on the toilet, raising the death toll to four.
So the three fugitives, with two bodies in suitcases in the trunk, drive to get rid of the bodies when they run into another car in town, in the rain, and meet some old little guy. They bribe him to forget about it.
They finally arrive at a remote spot to dump the bodies. Ah. make that one body, and a bloody suitcase that's open. Driving back to find the other body - did Josie's axe in the head actually do the deed? - they run straight into (and over) her, and kill her for sure. Just then, they hear police sirens. Charlie's wife, Penny (Natascha McElhone), who's the sheriff in town, stops them. One very quick adlibbed excuse later, and they are all down at the police station.
Little guy turns out to be the FBI agent Hymes (Jon Polito) sent to investigate the case of the local serial killer "the Oregon Undertaker", and he recognizes the gang. They somehow they get away with it all with only one body left to get rid of. They try the local tar pit, but as Charlie points out it'll take about a week for the body to actually sink. Agent Hymes shows up, having acted on his suspicions, and identifies Josie as the "Wyoming Widow" serial poisoner, and a running battle ensues. Hymes, who turns out to be a dirty agent, kills Gus as he's trying to make a run for it with the bag full of money. Josie and Charlie then kill Hymes with his own disease. Turning on Charlie just when he thinks it's all over, Josie kills him, but the joke is on her as she discovers that the bag of money, seen minutes before with $2 million in it, has a load of toys in it now... The camera cuts to Emily (Olivia Peterson), Charlie's daughter, having fun with a bag of bank notes.
In the final scene, Josie is shown hitching a lift with some guy with an Oregon license plate, who happens to have the body of a young woman in the back of his truck, just like the Oregon Undertaker.
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