Season 5, Episode 9: Road to Rupert

Recap: Brian accidentally sells Stewie’s teddy bear, Rupert, at a garage sale. This, of course, upsets Stewie, so Brian takes him on a cross-country road trip to Aspen, Colorado, to find him, where Stewie challenges the culprit to a ski-off to get him back. Meanwhile, Peter’s licence is suspended and Meg becomes his personal chauffer.

My take:

One of the best Family Guy episodes.

Intro starts like a Tom & Jerry clip. Rupert gets sold at a garage sale. Peter sells his anvil and buys his own racing gloves. Herbert makes an appearance looking to buy Chris’ shorts at the aforementioned garage sale. Even though he’s creepy, very creepy, Herbert cracks me up.