Timmy (Winslow Fegley) tells viewers in the trailer that he lives underneath the water tower in "Portland, Oregon—a place where things get strange." To help illustrate our city's well-documented oddball status, the segment cuts to a scene that resembles the annual Naked Bike Ride, only in Timmy Failure's world everyone has a little bit of clothing on. The procession is led by a shirtless Wallace Shawn bellowing toward the camera, who, at least to our knowledge, has not pedaled in the buff here before.