Reply To: Brookline
The song was taken from a Brooklyn, NY lecture series called Little Grey Books. It was hosted by John Hodgman (resident expert on The Daily Show) who hails from Brookline, MA. The topic of the particular night's lecture was BROOKLINE: The Town That Has Everything (and at the Same Time Has Nothing), for which Jonathan, being Musical Director for the series, had to write a song.
His wife is also from Brookline, which lends clarity to the whole ominous-city vibe of the song.