Jack Corcoran [Bill Murray] is a charismatic motivational speaker who promotes his best-selling book Get Over It. The film opens with a convention of recliner salesmen where he delivers a high-energy talk about overcoming hardship, using his own life as the prime example—how his father’s absence shaped his drive to succeed. At his engagement party, his agent Walter [Jeremy Piven] fills him in on a string of upcoming speaking engagements, and the two dream of landing a publicity-worthy gig that could spark an infomercial breakthrough.
The mood shifts when a series of telegrams arrives, including one from a Baltimore attorney about the estate of Jack’s recently deceased father, Kirby. Jack’s mother later confesses a long-held secret: she didn’t die and never intended for Jack to meet his father. She had left him, believing he would be a bad influence on Jack. Trusting a contract he’s shown by the Baltimore attorney, Jack signs with the assumption that it governs a substantial inheritance. Instead, the paperwork reveals only a lien of $35,000 tied to property damage caused by Vera, Kirby’s well-trained elephant from a traveling circus act. Kirby had left a cryptic note directing Jack to call “Blockhead” in Kansas City if Vera’s presence caused trouble.
With Vera suddenly in his hands, Jack seeks a way to monetize her talents. He consults Mo [Maureen Mueller] at the San Diego Zoo, who happens to be moving a herd of elephants to Sri Lanka, and she agrees to pay $30,000 for Vera. The plan is simple in theory: get Vera to Sri Lanka to join the herd and settle the debt. The journey begins with a train ride toward the West Coast, but a bribery demand from the conductor derails their progress, and Jack’s cash barely stretches to Kansas City, where he tracks down Blockhead, an old circus friend of Kirby’s. Blockhead starts to reveal the extent of Vera’s training, including a remarkable trick that Vera would perform only for Kirby: standing on her hind legs.
Blockhead points Jack to Terry Bonura, a seasoned Los Angeles-based trainer who works in show business. Terry offers $40,000 for Vera, shoring up Jack’s finances but widening the moral gap. On a failed attempt to reach Los Angeles, Jack’s vehicle breaks down, and he rents a semi-truck to press on, only to blow the transmission along the way. Stranded at a truck stop, Jack crosses paths with Tip Tucker [Richie Allan], a fast-talking, highly paranoid trucker bound for LA. A ruse involving a canceled load leads Tip to reluctantly agree to haul Vera to Los Angeles, but Tip soon realizes he’s been duped and becomes enraged.
The road trip veers into danger when a monsoon unleashes in New Mexico, threatening a village church. Vera acts as a stabilizing force, pressing her head against the walls to keep them from crumbling as villagers struggle to reinforce the structure. Jack then persuades Vera to demonstrate her strength by standing on her hind legs, bracing the church and enabling the villagers to secure safe passage for Vera and Jack onto a train bound for Los Angeles.
As the moment to sign with Terry approaches, Jack has a change of heart. He discovers that Terry’s operations rely on brutal treatment of elephants, including the use of an electric goad on other animals. He sabotages the deal by stealing one of Terry’s trucks and fleeing toward San Diego. Tip, who found Terry’s business card in the cab, races to catch up as Jack heads for the airport.
At the San Diego airport, Mo is loading her elephants onto a C-5 Galaxy cargo plane. Security initially blocks Jack and Vera from boarding because they aren’t on the manifest. In a tense sequence, Jack speeds a truck to the terminal, racing through the crowd to reach Mo on the tarmac. Tip closes in, waving Terry’s electric goad, and the guards must decide who poses a greater threat. They determine that Tip’s actions are the greater danger, allowing Jack and Vera to reunite with Mo before the cargo plane leaves.
Mo reveals that her budget is exhausted and Vera’s fate now lies in jeopardy. Jack confesses that he will miss Vera, but believes she would be better off with a capable elephant herd rather than with him. The final captions reveal a bittersweet but hopeful future: Jack leaves his fiancée for Mo, and the two witness Vera’s first calf being born in Sri Lanka. The rest of the cast’s fates are sketched in quick succession—Jack’s ex-fiancée moves on with his agent, and his mother’s life continues to be a complicated backdrop to his choices. Tip Tucker remains on the road, continuing his solitary wanderings, while Vera’s cross-continental journey becomes the basis for Jack’s memoir—a runaway bestseller that never saw a second printing, even as its real-life journey captured hearts.
