13. Road To Rupert
Season: 5
Episode: 9
Original Air Date: January 28th, 2007 It's yet another episode that is heavy on Brian and Stewie making travels together, this time to Aspen, Colorado to reacquire Stewie's teddy bear, Rupert, after it is accidentally sold during a Griffin family yard sale and the family who bought the bear have just moved away. After making their way towards Aspen, they find themselves needing to rent a helicopter to get over a snowy mountain. They find out that they can rent the helicopter by check, by cash, or by a jaunty tune. Stewie then performs a dance number with Gene Kelly (with Stewie animated over an actual scene from the 1945 musical, Anchors Aweigh), giving them the helicopter, only for Brian to crash it. Upon finally arriving in Aspen, they meet the buyer of Rupert, voiced by Rob Lowe (unfortunately not by Painfully Awkward Rob Lowe, Less Attractive Rob Lowe, or Super Creepy Rob Lowe), agrees to give Rupert back to Stewie, but only if Stewie can beat him in a downhill ski race. If the buyer wins, he gets to keep Brian. Stewie loses the race, but what fun would it be if Brian just left the show like that? They steal Rupert away, carjack a passing driver, and make their way home. Of all the "Road To..." episodes we've seen, this is easily the most plausible of the bunch, but that doesn't mean that it's really any less funny, which is nice.