Rupert gained possession of Herbie by the instruction of his boss, Simon Moore III. However, after failing to win any races with him, Simon tells Rupert to get rid of Herbie. So, he sends him off to the junkyard, where he is later entered in a mechanic's competition and comes into the ownership of Hank Cooper.
After Simon sees Herbie do amazing things he did not see him do before, he gets Rupert to find out more about him and his creator Dr. Gustav Stumpfel. After Simon convinces Stumpfel to build another car, Rupert brings in his favorite picture for the mixture as requested, which happens to be of himself. After Horace is created, Rupert offers to help carry out the destruction of Herbie, and takes Horace with him to get rid of the other car. He prepares to do the job himself, but Horace does the honors to brutally smash Herbie to dearth while Rupert watches in horror.
During the final race, Rupert serves as Simon's co-driver, and helps execute Horace's modifications. After they lose the race and Horace, both Rupert and Simon are arrested by the police.