Rupert Andrews was a young toff who bullied Dennis Tanner when Dennis joined Rupert and his friends Caroline Critchley, Jane Maxwell, Daniel Palmer and Michael Grafton on an outing to Oulton Park in 1965. There at Caroline's invitation, Dennis wasn't a friend of the group but a hairdresser at Gerard's Salon, asked along to the motor racing for a laugh.
Knowing Caroline, Rupert suspected "a slight case of Tanner-baiting" when he learned that Dennis came from the working-class Coronation Street. The ringleader of the group, Rupert immediately started picking on the lad, making fun of his ambition to open his own salon and mimicking his accent. When he realised that Dennis was desperate to make a good impression on his "new friends", Rupert began heckling him, offering to sell him his sports car for £500 when Dennis said that he was thinking about buying one to impress them (in reality, he barely had two pennies to rub together). Later, he got Dennis to pay for an extra round of drinks by pretending to have lost his wallet, knowing that Dennis wouldn't stand up to him.
When before the final race the group decided to move on without Dennis, Rupert spun the lad a yarn about them being asked to an invite-only party by the Fotherbys - who Dennis pretended to have heard of, despite Rupert having made the name up - in order to ditch him. As Dennis set off home, as a final insult Rupert made up directions which would supposedly take him to the nearest bus stop, leading Dennis on a wild goose chase. The hapless hairdresser arrived home hours later, penniless and crushed by the experience.