The film offers a comedic exploration of two simple-minded friends, Lloyd Christmas and Harry Dunne, navigating a series of misguided adventures. While the movie employs slapstick humor to entertain, it also provides an examination of how these characters, despite their profound ineptitude, manage to display a certain charm and innocence through their actions. The film cleverly unveils their story, beginning with Lloyd, a limousine driver who is deeply infatuated with a passenger, Mary Swanson. His simple infatuation sets the stage for an odyssey that he and his roommate Harry embark upon—an endeavor that challenges their friendship and tests the limits of their naiveté.

At its core, the plot relies heavily on the improbable actions of the protagonists. Lloyd's fixation on Mary becomes the catalyst for their road trip to Aspen, Colorado. After noticing Mary leave a briefcase at the airport, he retrieves it, unaware that it contains ransom money intended for a criminal exchange. This ignorance propels the narrative forward and serves as a consistent source of humor and tension. One could argue that the very essence of the film's comedic appeal lies in the naivety of Lloyd and Harry, which becomes apparent as they consistently misinterpret their environment—often with serendipitously advantageous results. The duo's ignorance is especially evident in their dealings with the thuggish antagonists, whose intimidation compels the two friends to flee their apartment.

The illogicality of their choices underscores the absurd nature of their journey. Following the theft of their van, Harry's parakeet is killed by the thugs—an event made more ludicrous when they later discover the unintentionally comical actions of these "men of the underworld." The film uses such sequences to amplify the inherently humorous dichotomy between the menacing intentions of the antagonists and the completely oblivious state of the protagonists. This dynamic is expanded upon as Lloyd and Harry decide to leave their chaotic lives in Providence behind, aiming to return the briefcase and simultaneously kindle a new life in Aspen. Harry, initially skeptical about the plan, is persuaded by Lloyd, highlighting a recurring theme of blind optimism that pervades their friendship.

As they venture towards Aspen, their escapades continue to illustrate their unawareness of danger and social cues. From fleeing a diner without paying to an accidental poisoning of one of the thugs, their journey is littered with a series of missteps rewarded with unforeseen benefits. Perhaps the most significant is their decision to open the briefcase, sparking a sequence of extravagant, yet imprudent expenditures including hotel stays and outlandish wardrobes. This comedic indulgence serves as a satirical critique of irresponsible consumption, yet remains endearing due to the good-natured idiocy of the protagonists. Their stewardship of the briefcase money is juxtaposed with the I.O.U.'s they fill, humorously underlining their misguided sense of responsibility.

However, the tension between Lloyd and Harry reaches its zenith when both misunderstand Mary's friendship with Harry as romantic interest. Their profound misinterpretation not only threatens their camaraderie but also complicates the increasingly tangled plot entwining them with Mary's kidnapping drama. Yet, their friendship underlies the narrative's emotional core. The climax entrains this chaos to its peak, with rebellious Lloyd seizing a chance to win over Mary, only to inadvertently become entangled in the kidnapping plot devised by the villainous Nicholas Andre.

The culmination of their journey showcases an unexpected layer of critique on gullibility and trust. As the FBI intervenes, revealing they were aware of the kidnapping ploy all along, the viewer is guided to reconsider the seeming triviality of Harry and Lloyd's exploits. Although oblivious to the intricacies of the crime, their pure intentions inadvertently foil the kidnappers' plans—demonstrating an ironically fortuitous ingenuity entangled in their foolishness. This resolution, while humorous, leaves an important point of reflection on simplicity and integrity contrasted with the complex machinations of crime and deceit.

The denouement of the film underscores a disheartening, yet comedic acceptance of their unchanged fate. Despite their fantastical sojourn, they inadvertently eschew a serendipitous opportunity for a glamorous future by unknowingly declining offers to become oil boys for Hawaiian Tropic models. This ending cleverly punctuates the movie's overarching message—the unpredictability of life's opportunities often lies hidden beneath the guise of absurdity. Lloyd optimistically assures Harry that their time will come, encapsulating the hopeful, albeit nonsensical, spirit the audience has come to love. The film, thus, creates an eloquent juxtaposition between their endless optimism and the unfortunate series of events that encapsulate their adventure, firmly rooting as a classic parable of unintended humor, friendship, and the pursuit of simplicity amidst complexity.