According to Allmusic critic Bill Janovitz, the two verses contrast the new baby James, as a lonely cowboy, in the first verse with the lonely grown-up James singing in the second verse. On the other hand, author James Perrone suggests that the young cowboy James in the first verse as well as the James traveling the Massachusetts Turnpike in the second verse are both the adult James who is singing the song. Perrone notes that the two are linked near the end of the song when Taylor sings that the nighttime dreams of the first stanza cowboy and the dreams of the second stanza traveller "still inspire all who 'take to the highway.'"