Lloyd Christmas and Harry Dunne are two good-hearted but dimwitted best friends and roommates living in
Providence, Rhode Island. Lloyd, a
chip-toothed limousine driver, is instantly smitten with his passenger Mary Swanson, who is flying to
Aspen, Colorado. She leaves a briefcase in the airport and Lloyd attempts to return it, unaware it contains ransom money she has left for criminals Joe "Mental" Mentalino and J. P. Shay. Her plane has already departed, and Lloyd falls out of the
jetway. Fired for leaving the scene of an accident, Lloyd returns home to learn that Harry, a
dog groomer, has also been fired for showing up late to a dog show with the dogs covered in food. Mental and Shay follow Lloyd home, but he and Harry mistake the crooks for
debt collectors and flee, returning later to find Harry's
parakeet has been decapitated. Lloyd convinces Harry that they should return Mary's briefcase, and they set off for Aspen in Harry's dog-styled van. Mental poses as a
hitchhiker and is picked up by Harry and Lloyd, who annoy him with their childish antics. Stopping for lunch, Mental plans to slip the duo
rat poison pills, but they prank him by putting
chili peppers in his burger, aggravating his
stomach ulcer. Mistaking the pills for his medication, they inadvertently kill him with the poison but continue their trip. At a gas station, Harry flirts with fellow Aspen-bound driver Beth, and unwittingly saves Lloyd from being assaulted by Sea Bass, a trucker they tricked earlier. Police wait to intercept the duo on the road to
Colorado, but Lloyd takes a wrong turn and drives all night through
Nebraska. Harry gives up on the journey, but Lloyd persuades him to continue after trading their van for a
minibike. The duo arrives in Aspen but cannot find Mary, and a frustrated Harry attacks Lloyd, breaking open the briefcase and discovering the money, which they use on a hotel suite and lavish spending spree. They read in the newspaper that Mary and her family are hosting a charity gala, where a nervous Lloyd asks Harry to talk to her on his behalf. However, Harry agrees to go
skiing with Mary instead, lying to Lloyd that he arranged a date for him. While Harry and Mary have an enjoyable time together, Lloyd waits at the hotel bar and encounters Beth. Visiting Mary's home, he realizes that Harry lied to spend the day with her himself. In retaliation, Lloyd serves him coffee laced with
laxatives, causing Harry to have diarrhea in Mary's broken toilet, while Lloyd reintroduces himself to Mary. Taking her to the hotel to return the briefcase, he confesses his love for her, but she rejects him. Nicholas Andre, a friend of the Swanson family, arrives, from whom Lloyd learns that Mary has a husband named Bobby, and that the money was for him, revealing himself as the mastermind behind the kidnapping. Nicholas holds them at gunpoint and is furious to discover that Harry and Lloyd spent the ransom, replacing it with
IOUs. Harry arrives and after a brief confrontation with Lloyd over Mary is shot by Nicholas, and plays dead before ineptly returning fire. An
FBI team bursts in, led by Beth, revealing that she's an agent on the kidnappers' case and prepared Harry with a
bulletproof vest and gun. Nicholas and Shay are arrested, and Mary and Bobby are reunited, much to Lloyd's dismay. With their trip rendered pointless and their hopes for the trip crushed, Harry and Lloyd travel home on foot, after all their purchases were confiscated and their minibike broke down. They encounter a busload of bikini models on a national tour, but ignorantly reject an offer to be their "oil boys". Harry tells Lloyd that they will get their "break" one day, and they play a game of
tag as they walk back to
Rhode Island. ==Cast==