James Taylor is not singing about himself in this song, but about the child who was named in his honor. Taylor wrote the song in 1969, when he drove on his way to Richmond, Virginia to see his older brother, the late Alex Taylor. James had recently returned to America after recording his first album in England, and he was shocked to learn that Alex had become a father for the first time in his absence.

Alex and his wife, Brent Taylor, had given birth to their first child, a baby son, which Brent wanted to name Richmond, after the city in which he was born. However, Alex wanted to name the child James, after his younger brother. So after a few arguments, the couple named the boy James Richmond Taylor. James was elated to discover that he had a new baby nephew, also named James. So the title can be a little confusing, since both the singer and his nephew are named James. The singer is James Vernon Taylor, while his nephew is James Richmond Taylor.

There are some ways this song associates with its writer. As a young child, James Taylor, along with his siblings, often sang each other to sleep at night. The story goes that James couldn’t stand it when his mother sang, because she only sang opera. And because James’ mother was a lyric soprano, she never sang lullabies. James’ father never sang lullabies either, because he didn’t exactly have the knack for music. So when he was a little boy, the young James Taylor was often put in the position of having to sing himself to sleep each night, hence the line, “Singin’ works just fine for me.”

Speaking with Rolling Stone in 2015, Taylor said this was his best song. “It starts as a lullaby, then the second half of the song – ‘the turnpike from Stockbridge to Boston’ – talks about what music means to me. It gets pretty spiritual by the end.”

Taylor spent considerable effort on the lyrics, whose verses he later said used the most intricate rhyming pattern of his career. One of the most famous parts of the lyric is:

Now the First of December was covered with snow
And so was the Turnpike from Stockbridge to Boston
Lord, the Berkshires seemed dream-like on account of that frostin’ With ten miles behind me and ten thousand more to go

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