Plot

Aiming for the top, law intern Rick tells his boss that he'll do anything--such as driving the boss' cute niece from Miami to Los Angeles and returning three days later well-prepared for the the bar exam.

Rick Robinson (Benjamin Gourley) is a ladder-climbing law intern from Miami with four days until the Bar Exam. Desperate to score points with his boss, Maxwell McAllister (Rutger Hauer), he commits to a favor he can't afford and ends up in a rundown truck headed to Los Angeles, California with his boss' possessions, his Hollywood-bound niece Michelle (Mila Kunis), and her pet pig. Amid hitchhikers, breakdowns, and assorted local yokels, Rick finds love, life, and maybe himself in this trans-American road trip from Hell.—Bob Hedlund

With only four days until the bar exam, an utterly unprepared law intern, Rick Robinson (Ben Gourley), is given a rare opportunity to score points with his boss, Maxwell McAllister (Rutger Hauer) and without thinking, commits to a favor he cannot afford. Maxwell asks Rick to move some stuff and take his niece along with him. Maxwell says that his niece is very beautiful, and he put her through college. Maxwell says that she is a bit of a talker and also a little wild. Maxwell warns Rick not to touch her. Maxwell selected Rick as he is an intern and really eager to please. Rick idolizes Maxwell, who is a partner at the firm, works 80 hours a week and has stress related physical ailments.

Rick reaches Maxwell's home at 8 am the next day. He finds instructions to pick up a U-Haul truck, and to pick his niece from an address in Savannah, Georgia, and drive them to an address in LA. Rick is given $300 for the task. Rick calls his friend Carl (Hubbel Palmer) for advise, and Carl says that having 3 days straight with a Southern girl is a chance of a life time which Rick should not pass up. Rick is worried that he will never be back in time for his bar exam. Rick reaches the U-Haul rental. The lady charges Rick per mile instead of $35.95 per day, and the bill comes to $2335. The truck has to be filled with gas every 100 miles. Rick takes the truck back to Maxwell's home to load it with the stuff that needed to be transferred.

Rick soon finds himself stuck in a grueling cross country road trip driving a rundown U-Haul truck carrying all his boss's worldly possessions. To make matters worse, Rick finds himself in charge of Mr. McAllister's bratty Hollywood-bound niece Michelle (Mila Kunis) and her out-of-control pet pig. Rick reaches Savannah to pick up Michelle, but she was having a going-away party with her friends. One of the friends serves Rick a drink due to which he falls unconscious and loses an entire night of driving. Rick and Michelle get underway the following day. As Rick is mad, Michelle distracts him by getting him to talk about his home. Michelle says that she is moving to LA as she is an aspiring actress.

The trip from Miami to Los Angeles meets several snags. The truck breaks down on a backwoods road in the deep South. Michelle ventures out into the deep woods and Rick has no option but to follow her. They come upon a shack in the woods, inhabited by a hillbilly family. The family invites Michelle and Rick for dinner. They also offer to fix the truck after they have had their meal. The family then gets into a Jacuzzi with Rick and Michelle, but Rick's clothes are burned by the hillbilly family kids who were providing them refuge for the night.

Later, Rick gets high from a hallucinating drug and goes on a bender, which results in him being knocked unconscious. Michelle starts screaming for help by the side of the road and Rick is rescued by a peculiar hitchhiker called Orlie (Jon Heder), who finds a motel room for him and Michelle. Orlie asks to accompany Rick and Michelle, and is accepted, as Rick believes he owes him a favor for his rescue. Michelle takes a shine to Orlie, and they proceed to have fun at Rick's expense. Orlie says that his physical body died, but then his spirit swapped places with another body. Rick complains that he had already lost enough time, and wanted to keep going, but Orlie forces him to stop by holding his breath.

After Orlie forces Rick into an unusual encounter in a fast-food restaurant lavatory, Rick decides to leave him behind. He and Michelle grow closer to one another, following a stop at a Texas beach. Rick permits Michelle to drive, despite the insurance liability, due to fatigue. He wakes to find Michelle has taken them to Wichita, Kansas and Rick's home. Consequently, Rick is forced into a painful confrontation with his mentally ill father, an experience for which Michelle apologizes. They grow even closer as Michelle relates her life growing up.

The pair travel to Colorado, where the truck runs out of gas. A semi in which Orlie is traveling as a passenger comes to their aid. Following a stop in a small town, the truck (and Michelle's pig) is stolen by men working for local crime boss "The Lady" (Billy Drago). The Lady forces Rick and Orlie to fight in a cage match before he returns the truck, impressed by the show they put on. Crossing into Utah, Orlie spots a landscape that matches a drawing in his notebook. He believes that he has switched bodies as some past moment when he was near death and believes that the person now occupying his body will arrive here. A switch can then take place. Orlie leaves Rick and Michelle, telling them to keep going.

As the window for Rick to safely arrive back in Miami for the bar exam narrows, he rejects Michelle's assertions that there is something special between them. Rick drives straight to Los Angeles, arriving in Malibu where Mr. McAllister is waiting for them at his beach-side property. He states that Rick has arrived late but does not appear overtly concerned. Realizing he must hurry to fly back to Miami, Rick rushes to the taxi McAllister has arranged for him, leaving Michelle asleep in the truck.

At the airport security checkpoint, Rick realizes he is making a terrible mistake as he observes the Polaroid photos Michelle has snapped throughout their trip. Knowing he is meant to be with Michelle, he scrambles out of the airport and returns to Malibu. Finding Mr. McAllister, Rick confesses his feelings for Michelle. McAllister, having heard similar sentiments from Michelle regarding Rick, thanks him for returning and asks him to take care of her. McAllister adds that his law firm will be opening a Los Angeles branch. The movie ends as Rick reunites with Michelle on the beach, and a man approaches Orlie back in Utah.