Jack Corcoran, played by Bill Murray, is a motivational speaker who is struggling to make it in his career. His main sponsor cancels his contract due to a lack of success, leaving him a few speaking gigs in small towns. One day, he receives a telegram informing him that his father has passed away and left him an inheritance. Excited by the possibility of a large sum of money, Jack rushes to the circus where his father worked, only to discover that his inheritance is a rather large Asian elephant named Vera.
Initially, Jack sees the elephant as a burden and tries to sell it off to the highest bidder. He meets zookeeper Mo, played by Matthew McConaughey, who is interested in buying Vera for his zoo, but their negotiations fall through. Then, he meets Terry, played by Linda Fiorentino, who owns a traveling animal show and is equally interested in Vera. Jack is torn between the two options when he decides to keep Vera and, with no other options, decides to take her on a cross-country trip to Terry's show.
As they make their way, Jack and Vera face numerous challenges, from crossing a busy highway to passing through small towns that aren't too welcoming to circus animals. Mo pursues Jack, trying to take Vera away from him, while Terry is at odds with Jack over her treatment of animals. Despite all the challenges, Jack and Vera's relationship grows stronger, and Jack learns to appreciate the joy and companionship that Vera brings to his life. In the end, Jack makes a decision that is best for Vera and sets her free in the wild, but not before he has changed his life for the better and gained a new perspective on what is truly important in life.
