The film opens at a convention of recliner salesmen, where Jack Corcoran (Bill Murray) gives a motivational speech based on his book Get Over It. Jack shares the example of his father dying before he was born as a difficult circumstance that must be overcome to succeed. At Jack's engagement party, his agent (Jeremy Piven) updates him on all of his upcoming speaking engagements, and the pair hope that one of the engagements is high profile enough to lead to an infomercial.
As the party winds down, Jack reads telegrams from well wishers. One of the telegrams is from an attorney in Baltimore about the large estate of his recently deceased father Kirk. Jack's mother, Vera, shortly admits that she lied about his father's death. In truth, she left him because she felt he would be a bad example for Jack.
The attorney in Baltimore shows Jack a contract which mentions $35,000. Thinking this is the size of his father's estate, Jack signs the contract. In fact, it is the amount of property damage that the attorney has suffered because of Vera, Kirby's elephant. Vera and Kirby were a traveling circus act, and she is a highly trained elephant. Kirby left a note for Jack that instructed him to call "Blockhead" in Kansas City if there are any problems with Vera. Jack contacts Mo (Janeane Garofalo) at the San Diego Zoo, who happens to be transporting a herd of elephants to Sri Lanka in a few days. She helps Jack ascertain that Vera is a breeding age female, and she agrees to pay $30,000 for the elephant.
Jack and Vera board a train bound for San Diego, but the conductor (Keith David) insists on a bribe. Jack's $600 only gets them as far as Kansas City, where he looks up Blockhead, who is an old circus buddy of Kirby's. Blockhead shows Jack the extent of Vera's training, including a photo of Vera standing on her hind legs, which was a trick that she would only do for Kirby. He puts Jack onto an animal trainer in Los Angeles named Terry Bonura (Linda Fiorentino) who works in show business. Terry offers Jack $40,000 for Vera. So, he and Blockhead attempt to drive to L.A., but his truck breaks down. Jack rents a semi-truck and continues on his own. With no experience driving a big rig, Jack blows out the transmission.
Stuck at a truck stop, he encounters Tip Tucker (Matthew McConaughey) who is a fast-talking, deeply paranoid trucker bound for L.A. Jack slips outside to call Tip's mobile phone, and he tricks Tip into thinking his load has been canceled. Tip agrees to take Jack and Vera to L.A. instead. Along the way, Tip makes a phone call and realizes he has been tricked by Jack. He attacks Jack with a tire iron, but Vera intervenes and saves Jack from a beating. Tip drives off threatening to come back with the police.
Jack and Vera walk into New Mexico to evade Tip. They stumble into a monsoon that is threatening to tear apart a village church. As the villagers struggle to hold the walls up, Vera intervenes, holding the wall up with her head. The wall still threatens to collapse, and Jack gets her to stand on her hind legs to brace the wall for good. The villagers help Jack and Vera board a train that will finally take them to L.A.
As he is about to sign the contract to sell Vera to Terry, Jack realizes that she subjects her animals to a grueling workload, and he witnesses one of Terry's trainers abusing another elephant with an electric goad. He steals one of Terry's trucks and drives to San Diego. Tip found Terry's business card in the cab of his truck, and he arrives just as Jack leaves.
At the San Diego airport, Mo is loading her elephants onto a cargo plane. The tarmac security guard will not let Jack and Vera in because they are not on the manifest. Jack pulls the truck into the passenger drop-off in front of the airport and races through the terminal with Vera. At gate security, Tip finally catches up to them, waving Terry's electric goad. Jack convinces the security guards that Tip is more of a threat than Vera, and they deal with Tip while Jack and Vera catch up to Mo on the tarmac.
Mo explains that she has spent her entire budget and has no money for Vera. Jack confesses to Mo that he will miss Vera, but he knows she would be better off with other elephants. The film ends with a series of captions that indicate Jack left his fiancee for Mo, and the couple witnessed the birth of Vera's first calf in Sri Lanka together. Jack's ex-fiancee married his agent and Jack's mother ran their life. Tip Tucker also managed to get away and is still roaming the roads of America. The captions conclude by saying that Get Over It never made it to a 2nd printing, but Jack's memoir of his cross-country trip with Vera was a runaway besteller.
- Bill Murray as Jack Corcoran
- Tai as Vera
- Matthew McConaughey as Tip Tucker
- Janeane Garofalo as Mo
- Jeremy Piven as Walter
- Pat Hingle as Vernon
- Linda Fiorentino as Terry Bonura
- Keith David as Hurst
- Tracey Walter as Wee St. Francis
- Harve Presnell as Trowbridge Bowers