Malcolm Smith wins a brand-new automobile, a 1956 Chrysler New Yorker convertible, at a movie theatre raffle. Steve Wiley, Dean Martin, a gambler from New York, obtains a counterfeit of the winning ticket and also claims that the car is his. The theatre manager declares them both winners and that they can split the car any way they want.
Steve needs to sell the car to pay off a gambling debt, but Malcolm wants to drive it to Hollywood to meet actress Anita Ekberg. In a bold move, he aims to turn the prize into a path toward stardom, while Steve keeps a more practical plan in mind. The situation grows tense as the two men press their case, each convinced they deserve the car for different reasons.
Steve claims to know Ekberg, and agrees to drive to Hollywood with Malcolm, secretly planning to steal the car. Along the way, Malcolm brings his formidable dog, a huge Great Dane named Mr. Bascomb, who consistently foils Steve’s attempts to slip away with the prize.
Their road trip takes an unexpected turn when they pick up Terry, Pat Crowley an aspiring dancer, who has a job waiting for her in Las Vegas. On the open road, the trio faces a string of comic mishaps and close calls as they navigate the lure of show business and the pressure of two rival ambitions.
In Las Vegas, Malcolm falls into a stretch of luck, feeling the casino's lucky atmosphere, and wins $10,000. The hotel where he lands also hosts the woman of his dreams, Anita Ekberg, who is there at the same time, leading to a meeting that carries both charm and chaos and delivers a few humorous moments.
Steve begins to show a change of heart. He not only agrees to go along with Malcolm to Hollywood without stealing the car, but he also proposes to Terry, signaling a shift in loyalties and a step toward a more straightforward future.
Malcolm spoils the mood by telling them that he no longer has any of his casino winnings, having used it on a gift for Anita. This revelation shifts the tone of their mission and rekindles tension about the gift, loyalty, and what they owe to each other.
Steve decides to retrieve the gift and they head to Paramount Pictures to locate her. The group traverses a series of back-lot adventures, encountering various cast and crew members, until they finally reach Anita and negotiate the terms of the gift’s return.
After some back-lot adventures, they find Anita, who agrees to return the gift in exchange for the services of Mr. Bascomb in her next movie. The resolution brings a comedic wrap-up to their cross-country drive, with a new sense of partnership emerging from the mismatched plans that originally brought them together.
