This song was written as a lullaby for James Taylor's infant nephew, also named James, who he was driving to meet for the first time. It blends the tenderness of a lullaby with the imagery of a cowboy song, with the chorus echoing the sentiment of "Rock-a-bye Baby." The lyrics contrast the new baby as a lonely cowboy with the lonely grown-up James singing, or perhaps both represent the adult James who is singing the song, linked by dreams that inspire those who "take to the highway." It's a deeply personal piece, considered by Taylor to be his best song, and appears as the title track on his 1970 album. Playing it feels like a warm, wandering journey of connection and reflection.