The song tells the story of Romeo and his wild-child neighbor and childhood friend, John Roy, two teens enroll in a small Texas college. John Roy decides from a young age that he and Romeo should go down to Mexico to pick up girls and party. The two enter Mexico but are detained by a border guard, who suspects illegal activity due to their possession of cash in United States dollars, and threatens them with "ten years in a Mexican jail." Since a "pocket full" of cash in a tourist's home currency is normally not reasonable grounds to suspect a crime, the song lyrics that compare the event to Paul McCartney's arrest in Japan for may be a hint that they had other items in their possession. Romeo blames John Roy for everything; the attempt fails, and both end up remaining best friends after the ordeal. The chorus quotes a portion of Van Morrison's "Brown Eyed Girl", as well as interpolating the "sha-la-la-la" vocal.
