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Movie starts off with introductions of the characters. Nick (Brendon Meyer) is checking out of the Venetian hotel in Las Vegas, after attending a friend's bachelor party. He's a little straitlaced, he even objects to his bill having several porno movie charges on it. His friend wants him to stay as the party is still going on, but he wants to get back to Chicago. Vera (Whoopi Goldberg) is meeting the daughter (Lanai Chapman) who she gave up for adoption. The Pear Family (John Lovitz and Kathy Najimi and two kids) are checking in for a vacation. Owen Templeton (Cuba Gooding Jr.) is drowning his sorrows, he is a football referee who blew the coin toss of overtime of a big game, and the Cody Brothers (Seth Green and Vince Vieluf, who speaks garbled throughout the move because of a swollen pierced tongue) attempt to fake an accident but fail, causing a woman to fall down the stairs (with lawyer Gloria Aldred in a cameo). All of them play the slots, and a gold coin appears in their winnings, which sends them to a penthouse office.
They meet each other, and Mr. Pollini (Rowan Atkinson) joins them. They are met by the billionaire owner of the casino, Donald Sinclair (John Cleese) and his lawyer Mr. Grisham (Dave Thomas). He has an interesting game for them. In Silver City, New Mexico, there is a train station locker with a bag containing $2 million. He gives them all identical keys with trackers, and tells them the first one there gets to keep the money
After some trepidation, they leave, except for Nick, who decides to not even participate. Unbeknownst to them, however, they are actually part of a human horse race, for Sinclair's highest rollers.
Now all the paths diverge, but meet up later, so I'll give the character's individual paths:
Is stranded at the airport (because of The Cody's sabotage of the airport radar, to keep the others from flying). Meets Tracy Faucet (Amy Smart) a helicopter pilot, and decides to try for the money, and he's also smitten with her. She takes him in a helicopter (which can fly, different radar system), but takes a detour, where she find's her boyfriend (Dean Cain) in the pool with his ex. She buzzes them and chases him, crashing the helicopter, and they are being close behind by the cops. She takes her truck which he was trying to get away in, and Nick, after some hesitation, joins her. He reveals the game, and they go on together.
After she and her daughter get into a rental car, they drive along and meet a crazy squirrel saleswoman (Kathy Bates). They don't buy a squirrel, but Bates gives them directions to what she says is a shortcut. It turns out to be a steep ravine, with signs saying "You should have bought a squirrel." Their car disabled, they wander in the desert to the salt flats, where a high speed car is trying to break the land-speed record.
They steal the car, and travel hundreds of miles. They end up disoriented and in the bus of a group of mental patients.
One of the kids sees a sign for a Barbie museum, but Lovitz doesn't want to stop (he hasn't told them of the game). Najimi forces him to stop, but it's not a museum about a doll, but of a Nazi. The Cody's sabotage their van, but the Pears see Adolf Hitler's touring car, and "borrow it". After accidentally ticking off a group of lady bikers, they crash into a W.W.II Veteran's Meeting, and nearly get shot. Lovitz finally tells Najimi the truth, and she doesn't want to continue. After seeing the Barbie Museum people at a rest stop, Lovitz puts sleeping pills in milkshakes knocking the rest of family out, and hitches a family ride with a truck driver.
He's in a taxi with a driver (Paul Rodriguez) who lost $20,000 on the game he was refereeing. He drives Owen to the desert, forcibly takes off his pants, and leaves him there. Owen walks till he sees a rest stop, along with a bus full of Lucille Ball impersonators, heading to a convention. After tricking the regular bus driver out of his uniform, he takes the bus and the impersonators. After running off the road due to a cow (more on that later) He tells the truth to the Lucy's, who chase him for ruining their vacation.
He gives them the slip, and gets on a horse.
After the sabotage at the airport and the museum, they decide to split up, so they have a copy of the key made. However the keymaker overhears them, and steals the key. They chase him to a hot-air balloon festival. They get the key back, and the keymaker is stuck in the balloon with a rope attached to the leg of a cow (which hits the windshield of Owen's bus, and which will be important later). They continue, but Vincent flirts with a girl with as many piercings as he does while driving. She flashes them, and they crash right into a line of cars about to be crunched by a monster truck at a speedway. They escape, and steal the truck.
Falls asleep standing up before he leaves the casino (he's narcoleptic). After he wakes, runs to catch a taxi but is hit by an ambulance (driven by Wayne Knight), who is delivering a human heart for a transplant.
They take a look at it, and promptly drop it, and then let it fall out of the window, and into the mouth of a dog. They recover it, but Knight thinks the heart is ruined, and eyes Atkinson to "replace" it. He somehow jumps onto a moving train headed for Silver City.
Sinclair and Grisham:
While all this is going on, they are doing sidebets with the gamblers, such as predicting what the middle of a chocolate from a sampler would be, and having Grisham give a ridiculous request to a call girl, and predicting what her price would be. (again, this is important.)
Finally, they all reach Silver City. Sinclair sends Grisham to the locker to declare the winner. Pollini gets there first, but falls asleep with the key in the locker. The others get there at the same time, and pull his key out and fight to put theirs in. The Cody's get it in the lock, open it and........it's empty.
Grisham and the call girl from earlier take off in a convertible with the moneybag. However, the keymaker in the balloon lands right on top of them. The cow is still attached to the balloon, and as the people in the convertible are fighting, the keymaker attaches the moneybag to the balloon, and the car crashes. The balloon floats away, with the money.
Sinclair takes the gamblers to Silver City, since all bets were still valid (in the meantime doing another side bet, having the pilot swerve violently to see who would be the last person to vomit). All of the others jump in a tour bus, and chase the balloon. They catch up with the balloon, and get to the bag, intending to share the money, when all of a sudden lights go up, and the group Smash Mouth is shown for a Feed the Earth concert. Everyone thinks the money is a donation, and everyone, even the Cody's (Seth needs some convincing from Vincent, who also meets the piercing girl from earlier, who can talk about as well as he can.) give the money to the charity.
Sinclair and all of the gamblers arrive, and Nick grabs the mike and announces that Sinclair was responsible for all this, because he wanted to do something for the planet, and that he and the other gamblers will happily match any donations made.
All of the racers end up in a mosh pit while Smash Mouth sings "All-Star" and the toteboard rings up over $20 million (which Sinclair and the other have to match to save face).
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