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Jim is a racing driver, who lost a car in an accident at the beginning of the first film. One day, he goes to a European car dealership in San Francisco, where he meets Carole Bennet, one of the employees, and finds an Apollo GT (the Thorndyke Special) car, but can't seem to afford that car. After meeting Peter Thorndyke, the owner of the dealership, and as he was looking for a price range of up to $80, Thorndyke thought Jim was out of his mind and then bids him good day. Then Herbie comes into Thorndyke's showroom, which makes Thorndyke mad. After he kicks Herbie and Jim stands up for Herbie after witnessing Thorndyke hitting, he leaves the dealership and somehow, Herbie manages to follow Jim home without Jim knowing.
The next morning, the police arrive at Jim's house, suspecting that he stole Herbie, which he didn't. Jim goes with the police detective back to the dealership and has an argument with Thorndyke and he ends up buying Herbie. He takes Herbie out for a drive on the freeway and Herbie gets scared heads back to the city streets and heads back to the dealership, where Jim thinks that Carole and Thorndyke had something to do with Herbie acting up. Then Carole drives Herbie with no problems and then Herbie starts to give Jim problems when he's behind the wheel, then later that night, Herbie does the same to Carole. Then that night, Jim does some adjustments to Herbie and then Herbie runs with no problems.
He ends up racing with Herbie and wins all the races, making headlines, even when Thorndyke races and tries to defeat Jim, he has no luck until one night when he and Carole go out with the Thorndyke Special, Thorndyke sabotages Herbie with whipped cream in his gas tank, where Jim ends up losing the next race. After that, Jim spends all his money on a Lamborghini, and decides to sell Herbie back to Thorndyke. Herbie gets upset, destroys the Lamborghini, and then runs away after feeling that Jim doesn't like him anymore. After tracking Herbie down to the Golden Gate Bridge, where he almost jumps, Jim was able to stop Herbie from jumping. He goes to the police station, where Herbie was taken after doing some damage to a local business in Chinatown, owned by Mr. Tang Wu.
Mr. Wu discovers that Herbie is a famous racing car and since Jim couldn't pay the damage, he and Wu make a deal that he can use Herbie to drive in the El Dorado race and if he wins, Wu can get the prize money and sell Herbie back to Jim for $1 and Wu accepts. Jim races the El Dorado with Carole and Tennessee Steinmetz together with Herbie and end up losing the first lap of the race due to sabotage and tricks by Thorndyke. The final half of the race, Herbie gets a late start due to their timing from the last lap and after fighting against Thorndyke on the race, Herbie breaks in half and takes 1st and 3rd place, where Jim becomes the champion. Jim and Carole get married and Herbie drives them off to their honeymoon, where he decides where they go.
Jim returns in the third installment of The Love Bug series. It's unknown whether he and Carole got divorced or separated after he came to Europe to drive foreign cars (which is mentioned in Herbie Rides Again), but it's never mentioned whether they are still together or not. Jim, his mechanic Wheely Applegate, and Herbie start racing in France. Herbie falls in love with a Lancia Montecarlo, which also has a mind of it's own, driven by a female driver, Diane Darcy, who thinks that Jim is trying to show off and get her attention. Jim tells her about Herbie, but she doesn't seem to believe him at first.
Jim competes in several races up until the Trans-France race from Paris to Monte Carlo, where his biggest rival in the race is the German driver, Bruno von Stickle. Jim and Herbie are way ahead of him until they spot Diane and her car in the river off the road. They rescue her from the river along with her car and they get back in the race. Herbie has trouble trying to get past Bruno until they enter a tunnel on the home stretch to Monte Carlo, where Herbie rides on the walls of the tunnel and gets in front of Stickle and they end up beating him in the race. Later that night, Jim and Diane have a dinner date and Herbie and Diane's Lancia do the same.
After Herbie's "death" from his malevolent counterpart Horace, Jim shows up at Herbie's memorial, along with Herbie's original builder Dr. Gustav Stumpfel. Jim tells Herbie's new owner, Hank Cooper that Herbie can be rebuilt, as long as the new car is built solely from the existing parts. When it comes time to start the car and Hank does not have a key, Jim volunteers a spare key he kept on hand. When Hank and Alex Davis tell Jim about Herbie forcibly taking them on a "date", Jim amusingly recalls Herbie having done this to him as well, noting this is how he met his wife. This is presumably a reference to Carole, suggesting the two are currently together, and no mention is made of Diane. Jim does not participate in the final race against Simon Moore III, but later poses with Hank and Dr. Stumpfel when Alex takes a photo of "the men in the car's life".