Freaks and Geeks (1999)

S6E24 The Great Race

Hank Thackery, proprietor of the Pixley House, a competitor to Shady Rest, devises a plan to launch a jitney service connecting Pixley and Hooterville, challenging the Cannonball. He wagers Joe that he can outpace the Cannonball from Pixley to Hooterville, with the loser serving as the other's bellboy for a month. Joe faces a major hurdle in motivating Wendell to adopt a racing mindset. Meanwhile, Hank persuades the county commissioner that the outcome of the race will determine the future of the Cannonball. In an unexpected twist, the Cannonball secures victory. Hal Smith guest stars as Jug Gunderson.