The movie opens with a shot of a man in a car with a JATO rocket strapped to it. The relevance of the opening isn't explained for some time as the movie shifts gears to a detailed look into the life of Michael Burrows, a criminal profiler for the San Francisco Police Department. Much of the film is shot in a documentary style, ostensibly as a part of a dissertation by a film school grad who follows Michael through the movie. Fired from the force after his haemophobia lets a murderer get away, he drifts about in a deep depression for several weeks before coming up with a way to combine his obsession with the Darwin Awards with his talent for profiling: help insurance companies detect, before they're sold insurance policies, people that are likely to end their own lives accidentally. After impressing a manager at the insurance company with his talent for profiling, he's paired up with Siri, a specialist in 'weird' insurance cases.
Siri and Michael travel the country investigating several legendary examples of stupidity on behalf of the insurance company, such as the above mentioned JATO rocket car, not all of which would qualify as 'Darwin Awards'. For example, a pair of men who are attempting to ice fish get frustrated and try to use a stick of dynamite to blast a hole in the ice only to have their trusty black lab fetch the stick of dynamite, run back to their brand-new SUV, and sink it to the bottom of the lake without either man being killed. As they investigate those and other cases, Michael tries to find a common factor in these people; the closest the movie gets to an explanation is a confused monologue by Siri about insurance companies always denying claims and driving people insane.
Ironically, Michael narrowly avoids becoming a Darwin Award winner throughout the movie. In one instance, he and Siri are stranded out in the middle of nowhere on a cold winter night. Desperate for warmth, he attempts to set a fire with gasoline to get warm only to blow up his own car. In a later scene, Siri confronts Michael, accusing him of being so obsessed with the Darwin Award winners because he suspects he's one of them.
A twist of fate leads to Michael finding out where the murder suspect he let get away lives. As he attempts to videotape the man in his home by rappelling down the side of his building, the film school student is seen for the first time. He, too, is hanging on the side of the building by a rope- with the other end of the same rope Michael is dangling by. The stone vase the pair is anchored by inches closer to the edge as the serial killer taunts them from the roof, slicing open his own hand in an effort to trigger Michael's haemophobia. Michael is able to overcome his haemophobia, defeat the serial killer, and live happily ever after with Siri.
The film opens with desert scenery, and within it, a secondary road. A dude with a pink sports car uses a JATO engine to drive. Fade to black, and sound of the car crashing onto something.
A voiceover explains the idea behind the Darwin Awards, given to people who did something so stupid which killed them, and so, removing themselves from the possibility of passing their dumb genes onto their offspring. Cut to a skyscraper, where aggressive executive Chris Hunter (Alessandro Nivola) shows off to two of his friends (Ross Patterson & Russell Steinberg) to prove that the glass is unbreakable and bullet-proof. He takes a cushion and jumps... as it happens to his death.
Cut to Michael Burrows (Joseph Fiennes), a criminal profiler for the San Francisco Police Department. It's decided that a documentary will be done about the way he works, so a cameraman (Wilmer Valderrama) will follow him everywhere. Two other detectives (Adonal Foyle and Tom Wright) wonder if the director should be there. Michael finds him a nuisance. He remembers when he realised that he can focus more than anyone else - on fourth grade, Michael (Max Common) realised that one of his fellow students (Vincent Brubaker) was the culprit of a prank, and so the whole class was punished without going out to the playground for the whole year. The boy hit Michael in front of his friends (Elias Stefanek, Zosha Stefanek & Emma C. Taylor) to make him not betray him, Michael's nose bled, he felt dizzy and passed out. It was found out that he had haemophobia - fear of blood.
Michael and the film maker are followed by a serial killer (Tim Blake Nelson). Michael is reading a book about his condition, but as he finds it useless, he throws it in a rubbish bin. He says that he's already done the killer's profile: a short man with literary studies. Michael realises that the killer is following them and he arrests him. As the film maker doesn't want to call the police - he would have to let go of his camera - that gives the opportunity for the killer to attack Burrows. Burrows handcuffs him anyway, but in the ensuing fight, the killer's nose bleeds. Michael passes out, the killer runs away and he punches the film director.
The film director keeps on recording Burrows, now expelled from the police because of his illness. Michael keeps on investigating from home - the cue is given by all the bills he has to pay, including insurance. He talks to an insurance executive (Kevin Dunn) to get a job with his company analysing risk-taking people. At first, the exec doesn't pay much attention, but Michael is able to rip his life apart describing every detail: his lovers, his spending habits, his use of slips as underwear which is causing fertility problems for him. Michael thinks that he will be able to profile people who take stupid risks. Michael also gives the example of fat men (R.J. Owens, Bruce Lee Sage & Bob Sáenz) who use soap bars in the shower, and when they try to pick up the bar, they die because they slip in the shower. Finally, the exec decides to give Michael an opportunity, as there are weird cases all over the United States which are costing the company millions. Michael doesn't want to travel, but he has to take the opportunity as it is.
He is paired with Siri Taylor (Winona Ryder), who investigates weird death cases. She is investigating a wacko cases in which Emile Travers (Ty Burrell) died in a freak case. There is blood all over the place, so Michael faints once again. The Zippy Cola dispensing machine won't work, so he tries to take the can of cola he's already paid for by introducing his arm through the slot, as he does with another dispensing machine which offers snacks. In the latter case he's successful, and steals a snack. He gets stuck, and the shopping mall where he's at closes for the night - and one of the cleaning men can't help him because he's wearing huge headphones as protection against the noise of the cleaning machine. Moreover, the mall is closing for the whole weekend. So Emile tries to pull his arm out. He finally succeeds in releasing himself, but the dispensing machine stumbles back and forth, and finally falls to the ground, smashing Emile as though he were a bug. As with the case of the jumping executive, Michael can picture himself being in that person's shoes doing the weird things that person did. Michael guessed that she had counted the coins and then falls to the ground.
Siri thinks that the legs of the Zippy Cola machine were faulty, so the insurance company will have to pay, but Michael proves otherwise, saving Zippy Cola millions of dollars.
Then, they go to Olson, Minnesota, to prove that the car robbery was fake, because in 32 there weren't any robberies there. Michael takes his own cutlery with him.
Michael focuses on the display fish on the wall of the owner of the stolen 4x4, Mr. Bob Sparrow (Max Perlich) while his wife Mrs. Sparrow (Mary Saudargas) offers them tea and biscuits. The only description he gives of the criminals is "weird men from the city". They go to a frozen lake. As Siri believes that accidents happen out of the blue, they argue. Siri walks on the ice; she slips down and lands on her back - that way, she realises that there's a frozen fish in a tree. Mr Sparrow is going through his midlife crisis, and buys the expensive car. One drinking day spent with his buddy Tom (Chris Penn), bored to death, and they decide to use dynamite to fish out of boredom. They are crappy dynamite users, so they use one to break the ice. But the dog of one of them brings them their dynamite. They run away, they even try to shoot the dog Max, but Max leaves the dynamite under the brand new car. When it explodes, that's the end of the car, and Mr Sparrow falls onto the hole and into the freezing water river. His buddy tries to take him out using his shotgun, which wounds him a little bit. So they throw it in the lake, which immediately freezes again. The police take the car out of the river. Michael thinks that Siri found the key to the crime with sheer luck, but Siri says that sometimes to have to take the risk of making a fool of yourself to accomplish things. Michael thinks that bravery equals stupidity many times.
Michael and Siri visit the wounded friend onto hospital.
They leave for Wendover, Nevada to investigate the disappearance of the wacko driver from the beginning. If they prove that there was a suicide attempt, there's no obligation for the company to pay.
Harvey Weston (David Arquette) likes shooting at old cars with his friend Stan (Brad Hunt).He's the man driving the pink car at the beginning. They are close to a gas station where Joleen (Juliette Lewis) works. Harvey admires a flashy red sports car. Joleen and Harvey make love, and Michael imagines himself making love to Joleen.
Harvey and Stan buy Army tools from two ex-Army soldiers (Myth Busters Adam Savage &Jamie Hyneman). There are grenades, masks... but they finally buy the engine of a military jet. Harvey drives the car with the intention of "being on TV". The engine is designed to empower jets of 200 tonnes, but Harvey's Chevrolet was only two. The car ended being at 650 kilometers per hour. He can't stop the car because the tyres melt at 400 km/h and the hand brake is ineffectual. He turns right, which causes the car to fly at 30 meters high until it crashes against a small steep. Mr. Pearlman (Richmond Arquette) watches it, and thinks it's a UFO. Mrs Pearlman (Nora Dunn) thinks that her husband is eccentric, and that he was distracted by they two quarrelling children (Allie Busch & Matthew Busch). The married couple talk to Siri and Michael. Siri refuses to pay insurance for somebody who has done such a daredevil thing.
They argue. Siri kisses him passionately to give him an opportunity to talk to a cashier called Zoe (Robin Tunney), pretending to split up with Siri. Siri thinks Zoe is desperate for sex and that she'll offer some "consolation" to Michael.
Michael ties himself with a weird harness in the shower, but it gets stuck. As usual, the film director won't help him, so Siri, in revenge, showers his camera. At that moment is when Joy phones him. Michael tells her he'll phone her in a minute, and Siri leaves him there.
Siri thinks that Michael is obsessed with the Darwin Awards because he's afraid he'll die in a stupid way.
A female executive, Carla (Julianna Margulies), in a plane is shown how the automatic pilot works by the pilot (Rod Arrants) himself. That gives her an idea: while driving a van she leaves the driving seat. She turns the automatic pilot on and then gives a blow job to her lover Henry (Tom Hollander). They cause a car driver (Debbie Brubaker) and a lorry driver to swerve wildly. The van crashes into a dentist (Josh Kornbluth)'s office, who was trying to calm down a panicky patient, Mr. Harris (Mickey Breitenstein). The intrusion of the van causes the dentist to hurt Mr Harries, who sues him. However, the marks of the executive's teeth on the dick of her partner are proof enough.
They drive to another location; they get lost and stuck in the middle of nowhere. Siri's phone is out of battery. Michael's phone flies away because he was trying to get some network. They try to fight the cold night by burning some petrol, thus setting fire to the whole car. Only when the batteries of the camera are dead will the film director take the trouble to use his working mobile phone with network. Siri and Michael hit him for not speaking before.
In Tacoma, Washington. Michael mentions two people who bring disgrace to others, but who are themselves immune to harm. Simon (Judah Friedlander) and his buddy Farley (Lukas Haas) go to a Metallica concert in a dirty van and already drinking some beer. Simon's mother (Nancy Clausen) wonders whether Simon has stolen money from her purse. They have to wait outside because the contact who is supposed to sell them their tickets doesn't show up. They try to buy the tickets from two fans (Jason Foster & Lindsay Benner) by giving them 200 bucks, marijuana and even their van. Simon remembers how Lisa Cummings sucked him off in that van, but complains that he's still a virgin.
They try to jump the wall inside the concert's venue. Simon ends up hanging in a tree. He cuts the wing of the tree with his knife, intending to fall onto a bush. They smoke some joints while doing that. Finally, Simon falls onto his own knife. Farley pulls Simon tying him to the van with a rope. But when he's about to pull him, a spark from his joint falls onto his trousers. Waving his arms and legs trying to put that out, Farley leads the van to fall on top of Simon, squashing him. The members of Metallica stop playing and stare at the weird view of the falling van. The driver survives, but Simon is squashed like a bug.
At the Deer Glen Motel, Michael smokes a joint to inspire himself. Michael is frustrated because he can't find any link to all those weird deaths. His job is secure, though, because he's saving the company so much money, as Siri tells him. Siri says that all the procedures in the insurance company lead to people quitting on fair claims.
Michael fights with two bar patrons (Jerry Harrison & John Doe) who laugh about Harvey Weston and Sparrow. Siri is haunted by all those weird deaths, but she tells Michael that he should try to forget it all. The film director is imprisoned in the bathroom so that he can't record their conversation. They kiss and make love.
Siri doesn't give any importance to that sexual relationship. Michael analyses her passion for one-night stands because her father abandoned her when she was a child. She pretends to cut herself to show the blood to him. He falls to the floor but then, it was only ketchup. A couple who are reading books (Michael Horowitz & Cynthia Horowitz) asks him whether he's all right.
The cameraman advises Michael to forget about Siri. At that moment, in their hotel room, Michael watches a reporter (Mike Sugerman) talking about the serial killer who has just killed again in South Beach. He realises that the victims were all reading books. He asks the film director to check that clue in his videotapes. The killer was carrying a beat poet's book in his pocket.
Michael leaves for San Francisco and an ex-workmate lets him in. The film director phones Siri, who watches the scene and describes it to him.
They go to Lawrence Ferlinghetti's book shop. When they finally talk to him, they lead him to a weird book buyer who tries to pass as a beatnik.
Michael hangs himself from a rope and records with the director's heavy camera the killer's apartment from a window. His bloodied boots are there. Siri insists on calling the police, but Michael refuses. The film director hangs himself as well with a smaller lighter camera, which proves to be too heavy for the stone fountain which they have tied the rope to. They tell Siri to go up to the rooftop and secure the fountain.
The killer watches them and he goes up to the rooftop and attacks Siri there, who is putting more weight inside the stone decoration. Michael gives his heavy camera to the film director. The imbalance in the weight makes the film director go down and Michael up. He reaches the rooftop and pulls the killer, holding onto his shirt. They all reach the street softly because of the new weight imbalance.
Once there, the killer asks Michael why he didn't kill him by letting him go from a height, but Michael said that it was just a reflex on his part. However, the decoration mold falls down onto the killer, who just says that he won't ever go on a drinking binge again. The killer is squashed.
The film director gets onto the ambulance recording it. The paramedic (Josh Charles) doesn't want to let him record because of the insurance, but Michael and Siri won't tell on him
Metallica dedicates a song to Simon, while his friend watches it from backstage in a wheelchair. He's so dumb that he lights a lighter close to the pyrotechnics which are to be used later for the concert.