Desperate to win a chance to sing with Dolly Parton, The Chipmunks enter a drawing only open to those born in Nashville. After they are selected as the winners and travel to Tennessee, the boys find themselves in Dolly's house. They find out they cheated Freddy, the runner up, and try to right their wrong but Alvin's scared. Freddy takes them to the county fair to see if they can catch a greased pig, rope a doogie, and ride a bull in the rodeo. During each test Alvin tries to tell Freddy the truth, but he doesn't listen. Later that night, Alvin gives Dolly Parton a call and tells her they can't perform at the concert for they are not from Nashville. However, Dolly and Freddy still want Alvin, Simon, and Theodore to perform with them, for they think The Chipmunks are country-at-heart.
- The title is a spoof of the film Urban Cowboy, starring John Travolta.
- The title shares its name with the album Urban Chipmunk.
- Dolly Parton is Alvin's favorite country singer.
- The episode reveals the fact that The Chipmunks (Alvin in this case) wear shorts underneath their jersey shirts.