[5] Deliberately a cross between a cowboy song and a lullaby, it was first thought up by Taylor as he was driving through Carolina to meet his infant nephew for the first time.

'"[12] On ABC's Good Morning America on September 15, 2008, Taylor acknowledged "there was that element" of being a "self lullaby" given the song's title and the "singing works just fine for me" lyric.

It is often saved for near or at the end of shows, where it serves as the emotional climax with Taylor performing it as the last encore coming back on stage without his band (as was the case for over a decade),[17] or perhaps with just a keyboard player accompanying his guitar.

[8] Taylor was born in Boston, and although he moved to North Carolina when very young, he spent summers in Massachusetts and went to boarding school there.

[4][18] This association has made Taylor a regional favorite in New England, including sell-outs at Tanglewood[9] and a record-setting concert stand at Great Woods.

[19] Taylor performed the song when campaigning for Deval Patrick's re-election during the Massachusetts gubernatorial election, 2010, and the "Stockbridge to Boston" line drew a huge reaction in that context as well.