High Quality Content by WIKIPEDIA articles! "Road to Rupert" is the ninth episode of season five of Family Guy. The episode follows Brian after he inadvertently sells Stewie`s teddy bear, Rupert, during a yard sale. In an attempt to retrieve him, Stewie and Brian travel across the United States, eventually discovering he is with a child living in Aspen, Colorado. Meanwhile, Peter has his driving license revoked for careless driving and is forced to be driven around by Meg, which annoys him.